Name: 332026-86-5|4-(1H-Benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine|98%
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SKU: A542473
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1
[ 332026-86-5 ]
3-amino-4-(1-ethyl-1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;
85%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Sergievskii; Krasnoshek; Mel'nikova; Tselinskii [Russian Journal of Organic Chemistry, 2002, vol. 38, # 6, p. 872 - 874]
[2]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

2
[ 107-13-1 ]
[ 332026-86-5 ]
[ 798578-48-0 ]

Yield	Reaction Conditions	Operation in experiment
68.7%	With pyridine; sodium methylate In methanol at 60℃; Cooling with ice;	1.2.1 (1) Preparation of compound 1a (3-[4-(1H-benzimidazol-2-yl)-1,2,5-oxadiazol-3-yl]amino}propionitrile): Dissolve 4-(1H-benzimidazol-2-yl)-1,2,5-oxadiazol-3-amine (18.2 g, 90.5 mmol) in 240 ml of anhydrous pyridine. After cooling in an ice water bath, a 30 mL methanol solution of sodium methoxide (8.8 g, 162.9 mmol) and acrylonitrile (6 mL, 90.5 mmol) were sequentially added. The reaction solution was stirred overnight at 60°C. After the completion of the reaction was detected by thin-layer silica gel chromatography, the reaction solution was evaporated to dryness under reduced pressure, 300 ml of water was added to the residue, and the mixture was extracted 3 times with 100 ml of ethyl acetate. The organic phases were combined, washed with 100 ml of saturated brine, dried with anhydrous sodium sulfate, and concentrated. The residue was recrystallized with ethyl acetate/n-hexane to obtain 15.8 g of white crystal product 1a with a yield of 68.7%.
	With sodium methylate In pyridine; methanol at 20℃; Cooling with ice;	1.A To an ice-cooled, stirred solution of 18.2 g of 4-(lH-benzoimidazol-2-yl)-furazan-3- ylamine (90.5 mmol, 1 eq) in 240 ml of pyridine are added 30 ml of sodium methoxide solution (30% in MeOH) (163 mmol, 1.8 eq) and subsequently 6 ml of acrylonitrile (90.5 mmol, 1 eq). The reaction mixture is stirred at room temperature overnight, before it is concentrated under reduced pressure. The residue is suspended in 250 ml of water and extracted with 4x 400 ml of ethyl acetate. The combined organic layers are washed with 2x 500 ml of brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product is dissolved in about 1000 ml of refluxing ethyl acetate. Then 1700 ml of n- hexane are added to the solution. The resulting turbid mixture is allowed to stand at room temperature overnight and the formed precipitate is filtered to provide 11.1 g of the product as light yellow solid. The filtrate is concentrated to dryness under reduced pressure and the residue is suspended in 100 ml of a 1/1 mixture of n-hexane / ethyl acetate. The suspension is filtered to provide 4.7 g additional product.MS (ESI+): 255 [M+H].1H NMR (400 MHz, DMSO-d6) ppm: 13.75 (broad, IH), 7.81 (broad, IH), 7.61 (broad, IH), 7.37-7.34 (m, 2H), 7.21 (t, IH, J=6 Hz), 3.68 (q, 2H, J=6 Hz), 2.94 (t, 2H, J=6 Hz).
	With sodium methylate In pyridine at 0℃;	6a Example 6a: 4- (1 H-BENZIMIDAZOL-2-YIL)-FURAZAN-3-YL-N- (2-CYANOETHYL)-AMINE To a solution OF 4- (1 H-BENZIMIDAZOL-2-YL)-FURAZAN-3-YLAMINE (0.10 g, 0.497 MMOL) in pyridine (5 ml) sodium in methanol (0.02 g, 0.86 mmol in 1 ml) and acrylonitrile (0.03 g, 0.39 MMOL) are added sequentially at 0°C. The mixture is stirred over night. Evaporation of the solvent under reduced pressure and partitioning of the resulting residue between water and ethyl acetate followed by drying of the organic solution over sodium sulphate gives the title compound in pure FORM. 1H-NMR (400 MHz, D6-DMSO) : 13. 7 (s, 1H) ; 7.82 (d, 1 H) ; 7.60 (d, 1 H) ; 7.36 (m, 2H); 7.20 (t, 1 H) ; 3.67 (q, 2H); 2.94 (t, 2H).

Reference： [1]Current Patent Assignee: YUNNAN BAIYAO GROUP CO., LTD.; YUNBAIYAO ZHENGWU SCIENT SHANGHAI - CN111454254, 2020, A Location in patent: Paragraph 0038-0044
[2]Current Patent Assignee: BASILEA PHARMACEUTICA - WO2011/12577, 2011, A1 Location in patent: Page/Page column 29; 31; 32
[3]Current Patent Assignee: BASILEA PHARMACEUTICA - WO2004/103994, 2004, A1 Location in patent: Page 41

3
[ 63823-75-6 ]
[ 332026-86-5 ]

Yield	Reaction Conditions	Operation in experiment
78.9%	With hydroxylamine hydrochloride; potassium hydroxide In diethylene glycol dimethyl ether; water at 20℃; for 6h; Cooling with ice; Reflux;	1.1 (1) 4-(1H-Benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine (Intermediate 1) The synthesis was carried out by taking 2-cyanomethylbenzimidazole (1 g, 6.36 mmol) in an eggplant-shaped flask.It was dissolved in acetic acid (10 ml), and an aqueous solution of sodium nitrite (0.44 g, 6.36 mmol) was added dropwise thereto in an ice bath, and a solid was formed, stirred for 40 minutes in an ice bath, and then filtered.The filter cake was washed once with water and twice with diethyl ether. Take another eggplant bottle,Hydroxylamine hydrochloride (0.53 g, 7.63 mmol) was added to the ice bath, and water was added as a solvent.Add potassium hydroxide (0.54 g, 9.54 mmol),Then add diglyme (6ml) and finally add the filter cake from the previous step.After the reaction system was raised to room temperature, heating was started and refluxed for 6 hours.Cooled to room temperature; a large amount of gold-pink crystals precipitated,Filter by suction, wash the filter cake once with water, wash twice with ether, and dry.The intermediate 4-(1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine is obtained(1.01 g, yield 78.90%).
78.9%	With hydroxylamine hydrochloride; water; potassium hydroxide In diethylene glycol dimethyl ether for 6h; Cooling with ice; Reflux;	1.1 (1) Synthesis of 4-(1H-benzo(d)imidazol-2-yl)-1,2,5-oxadiazol-3-amine (Intermediate 1) Take 2-cyanomethylbenzimidazole (1g, 6.36mmol) in an eggplant-shaped flask, dissolve it with acetic acid (10ml), add dropwise an aqueous solution of sodium nitrite (0.44g, 6.36mmol) under an ice bath, and a solid will form. After stirring for 40 minutes in an ice bath, filter with suction, and wash the filter cake once with water and twice with ether. Take another eggplant-shaped bottle, add hydroxylamine hydrochloride (0.53g, 7.63mmol) in an ice bath, add water as solvent, add potassium hydroxide (0.54g, 9.54mmol), and then add diglyme (6ml) Finally, add the filter cake of the previous step, return the reaction system to room temperature, start heating, reflux for 6 hours, and cool to room temperature; a large amount of gold-pink crystals are precipitated, filtered with suction, the filter cake is washed with water once, ether washed twice, and dried to obtain Intermediate 4-(1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine (1.01 g, yield 78.90%).
76%	With hydroxylamine hydrochloride; potassium hydroxide In diethylene glycol dimethyl ether at 110℃; for 6h;

	With hydroxylamine hydrochloride; potassium hydroxide In diethylene glycol dimethyl ether at 170℃; Cooling with ice;	1.A To an ice-cooled stirred solution of 13.2 g of hydroxylamine hydrochloride (190 mmol, 3 eq) in 20 ml of water, 15.3 g of potassium hydroxide (27.2 mmol, 4.3 eq) are slowly added. Then 60 ml of diglyme (diethylene glycol dimethyl ether) and 11.8 g of (IH- benzoimidazol-2-yl)-hydroxyimino-acetonitrile (63.4 mmol, 1 eq) are added. The ice-bath is removed and the reaction mixture is heated to reflux for 8h (bath temperature 1700C). After cooling to room temperature, the reaction mixture is filtered and the residue is washed with water to give the first crop of the desired product (6.2 g). The filtrate is treated with 150 ml of water. The resulting suspension is filtered and washed with water to provide a second product crop (2.17 g). Both crops are combined and used in the next step. MS (ESI+): 202 [M+H].1H NMR (400MHz, DMSO-d6) ppm: 13.7 (broad, IH), 7.78 (broad, 2H), 7.35-7.32 (m, 2H), 6.84(s, 2H).
	With hydroxylamine hydrochloride; potassium hydroxide In diethylene glycol dimethyl ether; water at 110℃; for 6h; Cooling with ice;

Reference： [1]Current Patent Assignee: CHINA PHARMACEUTICAL UNIVERSITY - CN109265451, 2019, A Location in patent: Paragraph 0032; 0033; 0034
[2]Current Patent Assignee: CHINA PHARMACEUTICAL UNIVERSITY - CN112920178, 2021, A Location in patent: Paragraph 0021; 0032-0034
[3]Li, Qi; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; Xiong, Baichen; He, Siyu; Lu, Weixuan; Liu, Yang; Yang, Hongyu; Li, Qihang; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [Journal of Medicinal Chemistry, 2020, vol. 63, # 17, p. 10030 - 10044]
[4]Current Patent Assignee: BASILEA PHARMACEUTICA - WO2011/12577, 2011, A1 Location in patent: Page/Page column 29; 31
[5]Li, Qi; Chen, Ying; Xing, Shuaishuai; Liao, Qinghong; Xiong, Baichen; Wang, Yuanyuan; Lu, Weixuan; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [Journal of Medicinal Chemistry, 2021, vol. 64, # 10, p. 6856 - 6876]

4
[ 3289-76-7 ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)-N-(2-chlorophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.
66%	With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 7h;

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]
[2]Li, Qi; Chen, Ying; Xing, Shuaishuai; Liao, Qinghong; Xiong, Baichen; Wang, Yuanyuan; Lu, Weixuan; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [Journal of Medicinal Chemistry, 2021, vol. 64, # 10, p. 6856 - 6876]

5
[ 332026-86-5 ]
3-amino-4-[1-(naphthalen-1-ylmethyl)-1H-benzimidazol-2-yl]-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

6
[ 332026-86-5 ]
3-amino-4-[1-(pyridin-2-ylmethyl)-1H-benzimidazol-2-yl]-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

7
[ 332026-86-5 ]
3-amino-4-[1-(pyridin-4-ylmethyl)-1H-benzimidazol-2-yl]-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

8
[ 332026-86-5 ]
3-amino-4-(1-[(6-bromobenzo[d][1,3]dioxol-5-yl)methyl]-1H-benzimidazol-2-yl)-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

9
[ 332026-86-5 ]
3-amino-4-[1-(2-chloro-6-fluorobenzyl)-1H-benzoimidazol-2-yl]-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

10
[ 332026-86-5 ]
3-amino-4-[1-(2-chlorobenzyl)-1H-benzimidazol-2-yl]-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

11
[ 332026-86-5 ]
3-amino-4-[1-(2-fluorobenzyl)-1H-benzimidazol-2-yl]-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

12
[ 332026-86-5 ]
2-[2-(4-aminofurazan-3-yl)-1H-benzimidazol-1-yl]-N-(2,4-difluorophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

13
[ 332026-86-5 ]
[ 333414-56-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

14
[ 332026-86-5 ]
2-[2-(4-aminofurazan-3-yl)-1H-benzimidazol-1-yl]-N-(2-oxo-2,3-dihydrobenzofuran-6-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

15
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)-N-(3,4,5-trimethoxyphenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

16
[ 332026-86-5 ]
2-[2-(4-aminofurazan-3-yl)-1H-benzimidazol-1-yl]-N-(3,4-difluorophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

17
[ 332026-86-5 ]
2-[2-(4-aminofurazan-3-yl)-1H-benzimidazol-1-yl]-N-(3-chloro-4-fluorophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

18
[ 332026-86-5 ]
2-[2-(4-aminofurazan-3-yl)-1H-benzimidazol-1-yl]-N-(3-chloro-4-methoxyphenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

19
[ 332026-86-5 ]
2-[2-(4-aminofurazan-3-yl)-1H-benzimidazol-1-yl]-N-(4-fluorobenzyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

20
[ 332026-86-5 ]
2-[2-(4-amino-furazan-3-yl)-1H-benzimidazol-1-yl]-N-[4-(trifluoromethoxy)phenyl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

21
[ 332026-86-5 ]
3-amino-4-[1-(3,4-diethoxybenzyl)-1H-benzimidazol-2-yl]-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

22
[ 332026-86-5 ]
3-amino-4-[1-(3-bromobenzyl)-1H-benzimidazol-2-yl]-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

23
[ 332026-86-5 ]
3-amino-4-[1-(3-fluorobenzyl)-1H-benzimidazol-2-yl]-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

24
[ 332026-86-5 ]
3-amino-4-[1-(3-methoxy-4-methylbenzyl)-1H-benzimidazol-2-yl]-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

25
[ 332026-86-5 ]
[ 696617-63-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

26
[ 332026-86-5 ]
3-amino-4-[1-(3-trifluoromethylbenzyl)-1H-benzimidazol-2-yl]-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

27
[ 332026-86-5 ]
[ 296771-04-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

28
[ 332026-86-5 ]
3-amino-4-[1-(4-cyanobenzyl)-1H-benzimidazol-2-yl]-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

29
[ 332026-86-5 ]
[ 328962-06-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

30
[ 332026-86-5 ]
3-amino-4-[1-(4-methylbenzyl)-1H-benzimidazol-2-yl]-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

31
[ 332026-86-5 ]
6-([2-(4-amino-furazan-3-yl)-1H-benzimidazol-1-yl]methyl)-1,3,5-triazine-2,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

32
[ 332026-86-5 ]
6-([2-(4-aminofurazan-3-yl)-1H-benzimidazol-1-yl]methyl)-2-dimethylamino-1,3,5-triazine-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

33
[ 332026-86-5 ]
2-[2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzimidazol-1-yl]-N-(3-fluoro-4-methylphenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

34
[ 332026-86-5 ]
3-amino-4-(1-[(6-chlorobenzo[d][1,3]dioxol-5-yl)methyl]-1H-benzimidazol-2-yl)-furazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; regioselective reaction;	4.1.3.1 Alkylation by benzylhalides 12′-39′ and 41′-43′ General procedure: A mixture of 3-amino-4-(1H-benzimidazol-2-yl)-furazan 9a-n (0.01mol), benzylhalide 12′-43′ (0.011mol), and K2CO3 (1.52g, 0.011mol), in dry DMF (30mL) was stirred at 80-90°C for 4-5h (reflux condenser was used for volatile benzylhalides). The mixture was cooled to room temperature and diluted with water (100mL). The precipitate was filtered and recrystallized from acetic acid. Yields of 12-39 and 41-43 were 70-90%.

Reference： [1]Stepanov, Andrei I.; Astrat'ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V. [European Journal of Medicinal Chemistry, 2015, vol. 94, p. 237 - 251]

35
2-chloro-N-(2-methylquinoline-6-yl)acetamide [ No CAS ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)-N-(2-methylquinolin-6-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.24%	With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 9h;	1.3 (3)2-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)-N-(2-methylquinolin-6-yl)acetamideSynthesis 2-Chloro-N-(2-methylquinolin-6-yl)acetamide (Intermediate 2, 194.41 mg, 0.83 mmol)In a tomato-shaped flask, DMF (6 ml) was added to dissolve.Then cesium carbonate (269.91 mg, 0.83 mmol) was added successively.And 4-(1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazole3-amine (intermediate 1, 150 mg, 0.75 mmol),After reacting at 70 ° C for 9 hours, a large amount of solid was precipitated by adding water, suction filtered, and washed twice with ethyl acetate.Wash twice with methanol, dry the filter cake to give a white solid.That is 2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)-N-(2-methylquinolin-6-yl)acetamide (Compound 1, 230 mg, yield 77.24%).TLC detected a point, the UV lamp had dark spots at 254 nm and no fluorescence at 365 nm.
	With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 9h;

Reference： [1]Current Patent Assignee: CHINA PHARMACEUTICAL UNIVERSITY - CN109265451, 2019, A Location in patent: Paragraph 0032; 0039; 0040
[2]Li, Qi; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; Xiong, Baichen; He, Siyu; Lu, Weixuan; Liu, Yang; Yang, Hongyu; Li, Qihang; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [Journal of Medicinal Chemistry, 2020, vol. 63, # 17, p. 10030 - 10044]

36
[ 105-36-2 ]
[ 332026-86-5 ]
ethyl 2-[2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl] acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.1%	Stage #1: 3-amino-4-(1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazole With caesium carbonate In acetonitrile at 20℃; for 0.25h; Stage #2: ethyl bromoacetate In acetonitrile	1.2 (2) 2-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1H-benzo(d)imidazol-1-yl)ethyl acetate (Intermediate 2) Synthesis Take 4-(1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine (Intermediate 1,1g, 4.97mmol) in an eggplant-shaped flask, and use acetonitrile ( 50mL) was dissolved, cesium carbonate (3.24g, 9.94mmol) was added, and after stirring at room temperature for 15 minutes, ethyl bromoacetate (1.66g, 9.94mmol) was slowly added dropwise to the reaction flask. After the addition, the solvent was removed under reduced pressure, dichloromethane and saturated sodium bicarbonate solution were added to the reaction flask, the mixed solution was transferred to a separatory funnel, the combined organic phases were collected, dried with anhydrous sodium sulfate, and removed under reduced pressure Solvent to give a pale yellow solid 2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl) ethyl acetate (intermediate 2,1.3g, the yield was 91.10%).

Reference： [1]Current Patent Assignee: CHINA PHARMACEUTICAL UNIVERSITY - CN112920178, 2021, A Location in patent: Paragraph 0021; 0035-0036

37
[ 227199-07-7 ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)-N-(benzo[d][1,3]dioxol-5-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 7h;

Reference： [1]Li, Qi; Chen, Ying; Xing, Shuaishuai; Liao, Qinghong; Xiong, Baichen; Wang, Yuanyuan; Lu, Weixuan; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [Journal of Medicinal Chemistry, 2021, vol. 64, # 10, p. 6856 - 6876]

38
[ 121221-08-7 ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)-N-(quinolin-5-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 7h;

Reference： [1]Li, Qi; Chen, Ying; Xing, Shuaishuai; Liao, Qinghong; Xiong, Baichen; Wang, Yuanyuan; Lu, Weixuan; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [Journal of Medicinal Chemistry, 2021, vol. 64, # 10, p. 6856 - 6876]

39
[ 347-66-0 ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)-N-(2-fluorophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 7h;

Reference： [1]Li, Qi; Chen, Ying; Xing, Shuaishuai; Liao, Qinghong; Xiong, Baichen; Wang, Yuanyuan; Lu, Weixuan; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [Journal of Medicinal Chemistry, 2021, vol. 64, # 10, p. 6856 - 6876]

40
[ 2564-03-6 ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)-N-(3-bromophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 7h;

Reference： [1]Li, Qi; Chen, Ying; Xing, Shuaishuai; Liao, Qinghong; Xiong, Baichen; Wang, Yuanyuan; Lu, Weixuan; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [Journal of Medicinal Chemistry, 2021, vol. 64, # 10, p. 6856 - 6876]

41
[ 17641-08-6 ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)-N-(3-methoxyphenyl)acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2021,vol. 64,p. 6856 - 6876

42
[ 874804-29-2 ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3,5-difluorophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3,5-difluorophenyl)acetamide (2). According to the general proceduredescribed above, compound 2 was synthesized with 2a and 1b, with ayield of 46%, mp 274-275 .C, 96.4% HPLC purity.1HNMR (300 MHz,DMSO-d6):11.07 (s, 1H), 7.89 (dd, J = 11.94, 7.64 Hz, 2H), 7.51-7.39d=(m, 2H), 7.33 (dd, J2.16, 9.50 Hz, 2H), 7.05 (s, 2H), 5.71-5.58 (m,= 2.16, 9.50 Hz, 2H), 7.05 (s, 2H), 5.71-5.58 (m,1H), 5.64 (s, 2H). 13C13CDMSO-d6):1H), 5.64 (s, 2H).NMR (100 MHz,166.32, 156.45,d141.95, 141.79, 138.66, 136.31, 132.81, 129.09, 125.26, 123.76,120.42, 120.09, 119.28, 115.72, 115.43, 111.41, 48.26. HR MS (m/z)calcd. for C17H12F2N6O2 [M + H]+ 371.1063 found 371.1061.+
46%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3,5-difluorophenyl)acetamide (2). According to the general proceduredescribed above, compound 2 was synthesized with 2a and 1b, with ayield of 46%, mp 274-275 .C, 96.4% HPLC purity.1HNMR (300 MHz,DMSO-d6):11.07 (s, 1H), 7.89 (dd, J = 11.94, 7.64 Hz, 2H), 7.51-7.39d=(m, 2H), 7.33 (dd, J2.16, 9.50 Hz, 2H), 7.05 (s, 2H), 5.71-5.58 (m,= 2.16, 9.50 Hz, 2H), 7.05 (s, 2H), 5.71-5.58 (m,1H), 5.64 (s, 2H). 13C13CDMSO-d6):1H), 5.64 (s, 2H).NMR (100 MHz,166.32, 156.45,d141.95, 141.79, 138.66, 136.31, 132.81, 129.09, 125.26, 123.76,120.42, 120.09, 119.28, 115.72, 115.43, 111.41, 48.26. HR MS (m/z)calcd. for C17H12F2N6O2 [M + H]+ 371.1063 found 371.1061.+

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]
[2]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

43
[ 33560-48-4 ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3,5-dichlorophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

44
[ 174700-38-0 ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3,5-dimethylphenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

45
[ 198488-19-6 ]
[ 332026-86-5 ]
dimethyl 5-(2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)acetamido)isophthalate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

46
C₈H₆Cl₂FNO [ No CAS ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3-chloro-5-fluorophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

47
C₈H₆BrCl₂NO [ No CAS ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3-bromo-5-chlorophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

48
C₉H₉ClFNO [ No CAS ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3-fluoro-5-methylphenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

49
[ 99585-91-8 ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3-chloro-5-methylphenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

50
C₉H₉BrClNO [ No CAS ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3-bromo-5-methylphenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

51
[ 630116-32-4 ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3-fluoro-5-(trifluoromethyl)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

52
C₉H₆Cl₂F₃NO [ No CAS ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3-chloro-5-(trifluoromethyl)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

53
C₉H₆Cl₂N₂O [ No CAS ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3-chloro-5-cyanophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

54
C₉H₆BrClN₂O [ No CAS ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3-bromo-5-cyanophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

55
2-chloro-N-(3-methyl-5-nitrophenyl)acetamide [ No CAS ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3-methyl-5-nitrophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

56
C₈H₆Cl₂N₂O₃ [ No CAS ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3-chloro-4-nitrophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

57
C₈H₆BrClN₂O₃ [ No CAS ]
[ 332026-86-5 ]
2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazole-1-yl)-N-(3-bromo-4-nitrophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With Cs₂CO₃ In N,N-dimethyl-formamide at 70℃;	General procedure: Intermediates 2a to 25a (1 mmoL) were dissolved in DMF (15 mL).Cesium carbonate (1.1 mmoL) and 1b (0.9 mmoL) were successivelyadded. The solution was stirred at 70 .C for 8 h, and then 40 mL of waterwas added into the reaction to produce a large amount of precipitation.The mixture was filtered and the residue was washed with water (30mL), then petroleum ether (20 mL) and then methanol (20 mL) to producedesired product 2 to 25. Some compounds were further purified bycolumn chromatography.

Reference： [1]Li, Qi; Xiong, Baichen; Wang, Yuanyuan; Lyu, Weiping; Xing, Shuaishuai; Chen, Ying; Liao, Qinghong; He, Siyu; Feng, Feng; Liu, Wenyuan; Chen, Yao; Sun, Haopeng [European Journal of Medicinal Chemistry, 2022, vol. 239]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	332026-86-5	MDL No. :	MFCD00501862
Formula :	C₉H₇N₅O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QEPDSNAEMKSMGN-UHFFFAOYSA-N
M.W :	201.18	Pubchem ID :	738531
Synonyms :

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P301+P310	UN#:	2811
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 332026-86-5 ] {[proInfo.proName]}

Quality Control of [ 332026-86-5 ]

Related Doc. of [ 332026-86-5 ]

Product Details of [ 332026-86-5 ]

Safety of [ 332026-86-5 ]

Application In Synthesis of [ 332026-86-5 ]

[ 332026-86-5 ] Synthesis Path-Downstream 1~57

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry