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Product Details of [ 13910-49-1 ]

CAS No. :	13910-49-1	MDL No. :	MFCD03001135
Formula :	C₁₁H₁₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	178.27	Pubchem ID :	-
Synonyms :

Safety of [ 13910-49-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P305+P351+P338	UN#:
Hazard Statements:	H302-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 13910-49-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 13910-49-1 ]

[ 13910-49-1 ] Synthesis Path-Downstream 1~23

1
[ 23873-65-6 ]
[ 13910-49-1 ]

Yield	Reaction Conditions	Operation in experiment
80.6%	With lithium aluminium tetrahydride In diethyl ether Reflux;	1.3 3 N-methyl-N-benzyl-3-aminopropionitrile 120g (0.69 mol) was added dropwise to a solution of 39.4 g (1.04 mol) of lithium aluminum hydride in diethyl ether, and heated to reflux. Slowly drip 20% sodium hydroxide solution, filter, mother liquor was spin-dried, and distilled to obtain 99 g of N-methyl-N-benzyl-3-aminopropyldiamine, the yield was 80.6%
	durch Reduktion;
	With ammonia; hydrogen In ethanol

	With ammonia; hydrogen In Petroleum ether
	With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h;	4.1.1. Synthesis of intermediate amines Va-c (Scheme 1) General procedure: Twenty five millimole of N-methylbenzylamine (3.03 g, 3.22 mL) and 30 mmol of ϖ-chloroalkanonitrile were refluxed with 30 mmol of anhydrous potassium carbonate (4.14 g) in 30 mL of anhydrous acetone for 3 h (reaction conditions A, Scheme 1). After cooling to rt and filtration, the solution was evaporated to dryness and the residue separated on SP1. A pale yellow oil was obtained that was identified through ESI-MS and NMR and used without further purification (IVa-c, yield 80-93%). A solution of 20 mmol of nitrile IVa-c in 50 mL of anhydrous THF was cannulated into a suspension of 1.25 g of lithium aluminum hydride (33 mmol) in 40 mL of anhydrous THF, kept under vigorous magnetic stirring at 0 °C (reaction conditions B). After 1 h the suspension was cautiously added with water until effervescence disappeared, then filtered and evaporated to dryness. Amines Va-c were obtained as pale yellow oils in a 61-84% yield, identified through ESI-MS and NMR and used without further purification.

Reference： [1]Current Patent Assignee: LIAONING KEJI PHARMACEUTICAL - CN108003141, 2018, A Location in patent: Paragraph 0032; 0037; 0049
[2]Shapiro et al. [Journal of the American Chemical Society, 1959, vol. 81, p. 3083,3084]
[3]Freifelder,M. [Journal of the American Chemical Society, 1960, vol. 82, p. 2386 - 2389]
[4]Roufos, Ioannis; Hays, Sheryl; Schwarz, Roy D. [Journal of Medicinal Chemistry, 1996, vol. 39, # 7, p. 1514 - 1520]
[5]Catto, Marco; Pisani, Leonardo; Leonetti, Francesco; Nicolotti, Orazio; Pesce, Paolo; Stefanachi, Angela; Cellamare, Saverio; Carotti, Angelo [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 1, p. 146 - 152]

2
[ 13910-49-1 ]
[ 14527-26-5 ]
[ 46737-78-4 ]

Reference： [1]Chemical and pharmaceutical bulletin,1967,vol. 15,p. 228 - 232

3
[ 221196-22-1 ]
[ 13910-49-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrazine hydrate In ethanol; water for 12h; Reflux;	1.1.3. General procedure for preparation of compounds 18 to 22 General procedure: Compound 13-17 (1 eq.) was dissolved in EtOH (100 mL for 2.5 to 5 g of phthalimide) and hydrazine hydrate (aqueous solution, 60% wt, 4 eq.) was added dropwise under stirring. The mixture was refluxed for 12 h and then cooled down to rt. The obtained suspension was filtered and the precipitate was washed thoroughly with EtOH. The filtrate was cooled in an ice-water bath and treated dropwise with a concentrated aqueous HCl solution (6 eq.). The formed solid was removed by fitration and washed with EtOH (approximately 100 mL for 5 g of phthalimide). One supplementary fraction of solid was removed by reacidification of the filtrate (if precipitate didn’t appear, the mixture was allowed to cool at 4 °C for 1 h). The filtrate was concentrated under reduced pressure, cooled in an ice-water bath and then gently dissolved in a minimum amount of an aqueous KOH solution (50% wt). The obtained solution was extracted with Et2O (3 × 75 mL for 5 g of phthalimide). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to afford a transparent to pale yellow oily liquid. This crude product was used directly for the next step or purified by distillation under reduced pressure to yield pure amines.
87.8%	With hydrazine hydrate In ethanol Reflux;	General procedure for the preparation of compounds 11-13. General procedure: Amixture of the compounds 8-10 (10mmol) and 80% Hydrazine hydrate solution (30 mmol) was added in 50 mL ethanol.The reaction mixture was heated under reux for 3-5 h, and ltered, the ltratewas concentrated under reduced pressure. The residue was dissolved indichloromethane (50 mL), washed with water (30 mL × 2) and saturated aqueous NaCl(30 mL), dried over Na2SO4, and filtered. The solventwas evaporated under reduced pressure. The residue was purified on a silica gelchromatography using mixtures of CH2Cl2/CH3OHas eluent to obtain the light yellow oil 11-13. N-Benzyl-N-methyl-propane-1,3-diamine(11a).Compound 8a was treated with 80%hydrazine hydrate solution according to the general procedure to give thedesired product 11a as light yellowoil, yield 87.8%.1HNMR (400 MHz, CDCl3) δ 7.26-7.19 (m, 5H), 4.27 (brs,2H), 3.43 (s, 2H), 2.81 (t, J = 6.4 Hz, 2H), 2.42 (t, J = 6.4 Hz, 2H), 2.16 (s, 3H), 1.70-1.66(m, 2H).
	With hydrazine hydrate In ethanol for 1h; Heating; Yield given;

	With hydrazine hydrate In ethanol for 5h; Reflux;
	With hydrazine hydrate In ethanol Reflux;	General procedure for the synthesis of intermediates 14-17a-d General procedure: 80% Hydrazine hydrate solution (8.0 mmol) was added to the solution of the corresponding compound 10-13a-d (1.6 mmol) in 20mL ethanol. The reaction mixture was heated to reflux for 4-5 h. After filteration, the filtrate was concentrated. The residue was dissolved in dichloromethane (40 mL), washed with water (20 mL×2) and saturated aqueous sodium chloride (20 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure to give intermediates 14-17a-d as light yellow oils in high purity. The products were dried over P2O5 under vacuum for 24 h and used for further reactions directly.
	With hydrazine hydrate In ethanol for 5h; Reflux;	4.1.3 General procedure for the synthesis of compounds 8-11 General procedure: Compounds 4-7 (10mmol) and 80% hydrazine hydrate solution (30mmol) were added in ethanol (50mL). The reaction mixture was heated under reflux for 3-5h, and then filtered, the filtrate was concentrated under reduced pressure. The residue was dissolved in dichloromethane (50mL), washed with water (30mL×2) and saturated aqueous sodium chloride (30mL), dried over Na2SO4, and filtered. The solvent was evaporated under reduced pressure to obtain compounds 8-11 as light yellow oil with high purity. The products were dried over P2O5 under vacuum for 24h and used for further reactions directly.
	With hydrazine hydrate In ethanol for 6h; Reflux;	1 4.1.4. General procedure for the synthesis of 10-12 General procedure: To a solution of N-aminoalkylphthalimide derivatives 7-9 (4 mmol)in ethanol (50 mL) was added hydrazine hydrate (1.23 mL, 20 mmol). The mixture was refluxed for 6 h. Then the solvent was removed under reduced pressure. The residue was diluted with 5% aqueous sodium hydroxide solution (20 mL) and the mixture was stirred for 0.5 h. Then the water (30 mL) was added and the mixture was extracted with dichloromethane(30 mL×3). The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give compounds 10-12 as colorless oil,which were used without further purification

Reference： [1]Ghedira, Donia; Voissière, Aurélien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valérie [European Journal of Medicinal Chemistry, 2018, vol. 158, p. 51 - 67]
[2]Pan, Wanli; Hu, Ke; Bai, Ping; Yu, Lintao; Ma, Qinge; Li, Tao; Zhang, Xu; Chen, Changzhong; Peng, Kelin; Liu, Wenmin; Sang, Zhipei [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2539 - 2543]
[3]Contreras, Jean-Marie; Rival, Yveline M.; Chayer, Said; Bourguignon, Jean-Jacques; Wermuth, Camille G. [Journal of Medicinal Chemistry, 1999, vol. 42, # 4, p. 730 - 741]
[4]Liu, Qiang; Qiang, Xiaoming; Li, Yan; Sang, Zhipei; Li, Yuxing; Tan, Zhenghuai; Deng, Yong [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 5, p. 911 - 923]
[5]Li, Yuxing; Qiang, Xiaoming; Li, Yan; Yang, Xia; Luo, Li; Xiao, Ganyuan; Cao, Zhongcheng; Tan, Zhenghuai; Deng, Yong [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 2035 - 2039]
[6]Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Xu, Rui; Cao, Zhongcheng; Song, Qing; Wang, Ting; Zhang, Xiaoyu; Liu, Hongyan; Tan, Zhenghuai; Deng, Yong [European Journal of Medicinal Chemistry, 2017, vol. 135, p. 307 - 323]
[7]Song, Qing; Li, Yan; Cao, Zhongcheng; Qiang, Xiaoming; Tan, Zhenghuai; Deng, Yong [Bioorganic Chemistry, 2019, vol. 84, p. 137 - 149]

4
[ 849473-02-5 ]
[ 13910-49-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogenchloride In 1,4-dioxane at 20℃; for 18h;	11 General procedure for the synthesis of substituted compounds 5a-c General procedure: The compound 1.3 (1 eq) was dissolved in 72mL of 3M HCl in dry 1,4-dioxane. The resulting mixture was stirred at room temperature overnight. Then, the solvent was removed under reduced pressure to give the desired product of sufficient purity for use without purification in the next step. 5.1.3.11 N1-Benzyl-N1-methylpropane-1,3-diamine (5a) (0037) Yield 98%. Mp: 77°C. 1H NMR (300MHz, CDCl3), δ: 11.27 (br s, 1H, NH); 8.37 (br s, 3H, NH); 7.66-7.41 (m, 5H, Haro); 4.27 (m, 2H, CH2), 3.27-2.28 (m, 4H, 2 CH2); 2.60 (s, 3H, CH3); 2.13 (p, J=7.4Hz, 2H, CH2). 13C NMR (75MHz, CDCl3) δ: 123.0 (Caro); 130.3 (Caro); 129.9 (2 Caro); 129.2 (2 Caro); 58.6 (CH2); 52.1 (CH2); 39.0 (CH3); 36.7 (CH2); 22.0 (CH2). LCMS m/z calc for [M+H+]: 179.1; found: 179.0.
	With trifluoroacetic acid In dichloromethane at 20℃; for 0.5h;
	Stage #1: [3-(benzylmethylamino)propyl]carbamic acid tert-butyl ester With trifluoroacetic acid In dichloromethane at 20℃; for 0.5h; Stage #2: With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 0.25h;

Reference： [1]Donnier-Maréchal, Marion; Carato, Pascal; Larchanché, Paul-Emmanuel; Ravez, Séverine; Boulahjar, Rajaa; Barczyk, Amélie; Oxombre, Bénédicte; Vermersch, Patrick; Melnyk, Patricia [European Journal of Medicinal Chemistry, 2017, vol. 138, p. 964 - 978]
[2]Gassiot, Amaury Cazenave; Charton, Julie; Girault-Mizzi, Sophie; Gilleron, Pauline; Debreu-Fontaine, Marie-Ange; Sergheraert, Christian; Melnyk, Patricia [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 21, p. 4828 - 4832]
[3]Location in patent: experimental part Toussaint, Marion; Mousset, Deborah; Foulon, Catherine; Jacquemard, Ulrich; Vaccher, Claude; Melnyk, Patricia [European Journal of Medicinal Chemistry, 2010, vol. 45, # 1, p. 256 - 263]

5
[ 13910-49-1 ]
[ 54880-50-1 ]
[ 1662697-41-7 ]

Yield	Reaction Conditions	Operation in experiment
57%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 24h;	1 4.1.10. General procedure for the synthesis of compounds 24-44 General procedure: To a mixture of the corresponding carboxylic acid derivatives 20-22 (0.21 mmol), EDCI (0.32 mmol) and HOBt (0.21 mmol) in THF were added the appropriate intermediates 11a-d, 12a-h, and 13a-d (0.25 mmol). The reaction mixture was stirred for 24 h at room temperature. The solvent was evaporated under reduced pressure. H2O (10 mL) was added to the residue and the mixture was extracted with dichloromethane (8 mL×3). The combined organic phases were washed successively with saturated aqueous NaHCO3 (5 mL×2) and saturated aqueous NaCl (10 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using petroleum ether/acetone (12:1) as eluent to obtain the corresponding compounds 24-44. 4.1.10.1 N-(3-(Benzyl(methyl)amino)propyl)-5-hydroxy-7-methoxy-4-oxo-4H-chromene-2-carboxamide (24) It was synthesized from 5-hydroxy-7-methoxy-4-oxo-4H-chromene-2-carboxylic acid (20) and N-benzyl-N-methylpropane-1,3-diamine (11a) according to the general procedure and gave compound 24 as a light yellow oil; 57% yield. 1H NMR (400 MHz, CDCl3) δ 12.51 (s, 1H), 9.11 (br s, 1H), 7.31-7.18 (m, 5H), 7.02 (s, 1H), 0.94 (d, J = 2 Hz, 1H), 5.95 (s, 1H), 3.74 (s, 3H), 3.59-3.54 (m, 4H), 2.66-2.63 (t, J = 5.6 Hz, 2H), 2.36 (s, 3H), 1.84 (br s, 2H). 13C NMR (100 MHz, CDCl3) δ 182.34, 165.77, 162.12, 158.37, 156.56, 155.59, 137.71, 129.08, 128.38, 127.34, 110.30, 106.02, 98.24, 92.73, 62.94, 56.77, 55.60, 41.81, 40.46, 24.60. HRMS-ESI [M+H]+ calcd for C22H24N2O5: 397.1685, found 397.1688.

Reference： [1]Liu, Qiang; Qiang, Xiaoming; Li, Yan; Sang, Zhipei; Li, Yuxing; Tan, Zhenghuai; Deng, Yong [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 5, p. 911 - 923]

6
[ 1016897-12-3 ]
[ 13910-49-1 ]
[ 1884491-74-0 ]

Yield	Reaction Conditions	Operation in experiment
82.3%	Stage #1: (E)-2-(4-(3,5-dimethoxystyryl)phenoxy)acetic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 3(-N-methyl-N-benzylamino)propylamine In tetrahydrofuran for 24h;	General procedure for preparation of derivatives of pterostilbene (18-21a-d) General procedure: A suspension of (1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 82 mg, 0.429 mmol) with compound 3 (90 mg, 0.286 mmol) in THF (2 mL) was stirred for 30 min at room temperature, then added the solution of the appropriate intermediates 14-17a-d (0.343 mmol) in THF (2mL). The solvent was evaporated after stirring for 24 h. The residue was dissolved in dichloromethane (40 mL), washed with water (20 mL×2) and saturated aqueous sodium chloride (20 mL), dried over sodium sulfate, and filtered. After being concentrated, the crude product was purified by column chromatography to afford 18-21a-d.

Reference： [1]Li, Yuxing; Qiang, Xiaoming; Li, Yan; Yang, Xia; Luo, Li; Xiao, Ganyuan; Cao, Zhongcheng; Tan, Zhenghuai; Deng, Yong [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 2035 - 2039]

7
[ 537-98-4 ]
[ 13910-49-1 ]
[ 1909254-81-4 ]

Yield	Reaction Conditions	Operation in experiment
57.3%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 8h;	General procedure for thepreparation of compounds 15-17. General procedure: To a mixture of ferulic acid (0.5 mmol), the corresponding compounds 11-13 (0.6 mmol), EDCI (0.75 mmol) and HOBT (0.5 mmol) was added in CH2Cl2 (3ml). The mixture was stirred at room temperature for 8h, and then CH2Cl2(20ml) was added, washed with 30% NaHCO3 (20 mL×2) and saturated aqueous NaCl (20 mL), dried over Na2SO4, and filtered. The solvent was evaporated to drynessunder reduced pressure. The residue was purified on a silica gel chromatographyusing mixtures of CH2Cl2/CH3OH as eluent toobtain the oil products 15-17(E)-N-(3-(benzyl(methyl)amino)propyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide(15a).Ferulic acid was treated with compound 11a according to the general procedure to give the desired product 15a as colorless oil, yield 57.3%. 1HNMR (400 MHz, CDCl3) δ 7.46 (d, J= 15.6 Hz, 1H), 7.34 (brs, 1H), 7.33-7.27 (m, 5H), 6.97 (d, J = 7.2Hz, 1H), 6.93 (s, 1H), 6.89 (d, J = 7.2 Hz, 1H), 6.14 (d, J = 15.6 Hz, 1H), 5.58 (brs, 1H), 3.86(s, 3H), 3.55 (s, 2H), 3.49-3.46 (m, 2H), 2.58 (t, J = 7.6 Hz, 2H), 2.25 (s, 3H), 1.81-1.75 (m, 2H). 13C NMR (100MHz, CDCl3) δ 166.29, 147.46,146.89, 140.34, 138.36, 129.38 (2C), 128.50 (3C), 127.37, 121.96, 118.67,114.86, 109.79, 62.64, 56.24, 55.91, 41.78, 39.35, 25.56. MS(ESI) m/z 355.2 [M+ H]+.

Reference： [1]Pan, Wanli; Hu, Ke; Bai, Ping; Yu, Lintao; Ma, Qinge; Li, Tao; Zhang, Xu; Chen, Changzhong; Peng, Kelin; Liu, Wenmin; Sang, Zhipei [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2539 - 2543]

8
[ 13910-49-1 ]
[ 65-85-0 ]
[ 1328467-33-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: benzoic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 3(-N-methyl-N-benzylamino)propylamine With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	20 General procedure E2 General procedure: Reaction was carried out under nitrogen atmosphere. In 10mL of DCM, benzoic acid (1 eq), HOBt (1.2 eq) and HBtu (1.2 eq) were added and stirred at room temperature for 10min. A solution of N,N-disubstitutedalkyldiamine 5a-f or commercially available amine (1 eq) and DIEA (15 eq) in DCM was added to the reacting mixture. After stirring at room temperature for 24h, the solvent was removed under reduced pressure and DCM was added to the residue. The solution was washed with a solution of NaHCO3 (5%) then saturated NaCl solution. The organic layer was dried over magnesium sulphate and evaporated under reduced pressure. The crude product was purified by thick layer chromatography (DCM:MeOH(NH3), 9:1 (v/v)) or column chromatography (DCM:MeOH(NH3), 9:1 (v/v)). 5.1.3.20 N-[3-(N-benzyl-N-methylamino)propyl]benzamide (7a) (0046) Procedure E2. Purification by thick layer chromatography was performed. Yield: 75%. 1H NMR (300MHz, CDCl3), δ: 8.05 (br s, 1H, NH); 7.70 (m, 2H, H2, H6); 7.49-7.30 (m, 3H, H3, H4, H5); 7.29-7.22 (m, 5H, Haro); 3.61-3.52 (m, 4H, 2 CH2); 2.65 (t, J=6.7Hz, 2H, CH2); 2.29 (s, 3H, CH3); 1.84 (p, J=6.8Hz, 2H, CH2). 13C NMR (75MHz, CDCl3) δ: 167.3 (CO); 137.8 (Caro); 134.7 (Caro); 131.1 (2 Caro); 129.4 (2 Caro); 128.4 (Caro); 128.4 (2 Caro); 127.4 (Caro); 126.9 (2 Caro); 63.1 (CH2); 56.9 (CH2); 41.6 (CH3); 40.1 (CH2); 25.3 (CH2). LCMS m/z calc for [M+H+]: 283.2; found: 283.1. HPLC (C4, 35min): tR 17.5min, PHPLC 97%; HPLC (C18, 35min): tR 15.2min, PHPLC 99%.

9
[ 52710-27-7 ]
[ 13910-49-1 ]
[ 1844838-53-4 ]

Yield	Reaction Conditions	Operation in experiment
61%	With triethylamine In dichloromethane at 0 - 20℃; for 12h;	21 5.1.3.18 General procedure E1 General procedure: A solution of N,N-disubstitutedalkyldiamine 5a-f or commercially available amine (1 eq), and triethylamine (3 eq) in 10mL of DCM was cooled at 0°C. A solution of substituted benzoylchloride (1 eq) in 5mL of DCM was added slowly. The resulting mixture was stirred at room temperature overnight. The solution was evaporated under reduced pressure. An aqueous solution of 3% sodium hydroxide (20mL) was added and the mixture was stirred for 1h. The solution was extracted with DCM. The organic layer was dried over magnesium sulphate and concentrated to give an oily product. The residue was purified by thick layer chromatography (DCM:MeOH(NH3), 9:1 (v/v)) or column chromatography (DCM:MeOH(NH3), 9:1 (v/v)).

10
[ 13910-49-1 ]
[ 329-15-7 ]
[ 1328397-48-3 ]

Yield	Reaction Conditions	Operation in experiment
57%	With triethylamine In dichloromethane at 0 - 20℃; for 12h;	24 5.1.3.18 General procedure E1 General procedure: A solution of N,N-disubstitutedalkyldiamine 5a-f or commercially available amine (1 eq), and triethylamine (3 eq) in 10mL of DCM was cooled at 0°C. A solution of substituted benzoylchloride (1 eq) in 5mL of DCM was added slowly. The resulting mixture was stirred at room temperature overnight. The solution was evaporated under reduced pressure. An aqueous solution of 3% sodium hydroxide (20mL) was added and the mixture was stirred for 1h. The solution was extracted with DCM. The organic layer was dried over magnesium sulphate and concentrated to give an oily product. The residue was purified by thick layer chromatography (DCM:MeOH(NH3), 9:1 (v/v)) or column chromatography (DCM:MeOH(NH3), 9:1 (v/v)).

11
[ 586-76-5 ]
[ 13910-49-1 ]
[ 1328023-71-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: 4-Bromobenzoic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 3(-N-methyl-N-benzylamino)propylamine With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	32 General procedure E2 General procedure: Reaction was carried out under nitrogen atmosphere. In 10mL of DCM, benzoic acid (1 eq), HOBt (1.2 eq) and HBtu (1.2 eq) were added and stirred at room temperature for 10min. A solution of N,N-disubstitutedalkyldiamine 5a-f or commercially available amine (1 eq) and DIEA (15 eq) in DCM was added to the reacting mixture. After stirring at room temperature for 24h, the solvent was removed under reduced pressure and DCM was added to the residue. The solution was washed with a solution of NaHCO3 (5%) then saturated NaCl solution. The organic layer was dried over magnesium sulphate and evaporated under reduced pressure. The crude product was purified by thick layer chromatography (DCM:MeOH(NH3), 9:1 (v/v)) or column chromatography (DCM:MeOH(NH3), 9:1 (v/v)).

12
[ 456-22-4 ]
[ 13910-49-1 ]
[ 1259181-34-4 ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: 4-Fluorobenzoic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 3(-N-methyl-N-benzylamino)propylamine With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	33 General procedure E2 General procedure: Reaction was carried out under nitrogen atmosphere. In 10mL of DCM, benzoic acid (1 eq), HOBt (1.2 eq) and HBtu (1.2 eq) were added and stirred at room temperature for 10min. A solution of N,N-disubstitutedalkyldiamine 5a-f or commercially available amine (1 eq) and DIEA (15 eq) in DCM was added to the reacting mixture. After stirring at room temperature for 24h, the solvent was removed under reduced pressure and DCM was added to the residue. The solution was washed with a solution of NaHCO3 (5%) then saturated NaCl solution. The organic layer was dried over magnesium sulphate and evaporated under reduced pressure. The crude product was purified by thick layer chromatography (DCM:MeOH(NH3), 9:1 (v/v)) or column chromatography (DCM:MeOH(NH3), 9:1 (v/v)).

13
[ 51-44-5 ]
[ 13910-49-1 ]
N-[3-(N-benzyl-N-methylamino)propyl]-3,4-dichlorobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	Stage #1: 3,4-dichlorbenzoic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 3(-N-methyl-N-benzylamino)propylamine With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	36 General procedure E2 General procedure: Reaction was carried out under nitrogen atmosphere. In 10mL of DCM, benzoic acid (1 eq), HOBt (1.2 eq) and HBtu (1.2 eq) were added and stirred at room temperature for 10min. A solution of N,N-disubstitutedalkyldiamine 5a-f or commercially available amine (1 eq) and DIEA (15 eq) in DCM was added to the reacting mixture. After stirring at room temperature for 24h, the solvent was removed under reduced pressure and DCM was added to the residue. The solution was washed with a solution of NaHCO3 (5%) then saturated NaCl solution. The organic layer was dried over magnesium sulphate and evaporated under reduced pressure. The crude product was purified by thick layer chromatography (DCM:MeOH(NH3), 9:1 (v/v)) or column chromatography (DCM:MeOH(NH3), 9:1 (v/v)).

14
[ 51-36-5 ]
[ 13910-49-1 ]
N-[3-(N-benzyl-N-methylamino)propyl]-3,5-dichlorobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%		General procedure: Reaction was carried out under nitrogen atmosphere. In 10mL of DCM, benzoic acid (1 eq), HOBt (1.2 eq) and HBtu (1.2 eq) were added and stirred at room temperature for 10min. A solution of N,N-disubstitutedalkyldiamine 5a-f or commercially available amine (1 eq) and DIEA (15 eq) in DCM was added to the reacting mixture. After stirring at room temperature for 24h, the solvent was removed under reduced pressure and DCM was added to the residue. The solution was washed with a solution of NaHCO3 (5%) then saturated NaCl solution. The organic layer was dried over magnesium sulphate and evaporated under reduced pressure. The crude product was purified by thick layer chromatography (DCM:MeOH(NH3), 9:1 (v/v)) or column chromatography (DCM:MeOH(NH3), 9:1 (v/v)).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 138,p. 964 - 978

15
[ 13910-49-1 ]
[ 100-09-4 ]
[ 1043061-65-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: 4-methoxybenzoic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 3(-N-methyl-N-benzylamino)propylamine With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	40 General procedure E2 General procedure: Reaction was carried out under nitrogen atmosphere. In 10mL of DCM, benzoic acid (1 eq), HOBt (1.2 eq) and HBtu (1.2 eq) were added and stirred at room temperature for 10min. A solution of N,N-disubstitutedalkyldiamine 5a-f or commercially available amine (1 eq) and DIEA (15 eq) in DCM was added to the reacting mixture. After stirring at room temperature for 24h, the solvent was removed under reduced pressure and DCM was added to the residue. The solution was washed with a solution of NaHCO3 (5%) then saturated NaCl solution. The organic layer was dried over magnesium sulphate and evaporated under reduced pressure. The crude product was purified by thick layer chromatography (DCM:MeOH(NH3), 9:1 (v/v)) or column chromatography (DCM:MeOH(NH3), 9:1 (v/v)).

16
[ 13910-49-1 ]
[ 98-60-2 ]
[ 1328902-85-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With triethylamine In dichloromethane at 0 - 20℃; for 12h;	54 5.1.3.18 General procedure E1 General procedure: A solution of N,N-disubstitutedalkyldiamine 5a-f or commercially available amine (1 eq), and triethylamine (3 eq) in 10mL of DCM was cooled at 0°C. A solution of substituted benzoylchloride (1 eq) in 5mL of DCM was added slowly. The resulting mixture was stirred at room temperature overnight. The solution was evaporated under reduced pressure. An aqueous solution of 3% sodium hydroxide (20mL) was added and the mixture was stirred for 1h. The solution was extracted with DCM. The organic layer was dried over magnesium sulphate and concentrated to give an oily product. The residue was purified by thick layer chromatography (DCM:MeOH(NH3), 9:1 (v/v)) or column chromatography (DCM:MeOH(NH3), 9:1 (v/v)).

17
[ 2905-60-4 ]
[ 13910-49-1 ]
N-[3-(N-benzyl-N-methylamino)propyl]-2,3-dichlorobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With triethylamine In dichloromethane at 0 - 20℃; for 12h;	34 5.1.3.18 General procedure E1 General procedure: A solution of N,N-disubstitutedalkyldiamine 5a-f or commercially available amine (1 eq), and triethylamine (3 eq) in 10mL of DCM was cooled at 0°C. A solution of substituted benzoylchloride (1 eq) in 5mL of DCM was added slowly. The resulting mixture was stirred at room temperature overnight. The solution was evaporated under reduced pressure. An aqueous solution of 3% sodium hydroxide (20mL) was added and the mixture was stirred for 1h. The solution was extracted with DCM. The organic layer was dried over magnesium sulphate and concentrated to give an oily product. The residue was purified by thick layer chromatography (DCM:MeOH(NH3), 9:1 (v/v)) or column chromatography (DCM:MeOH(NH3), 9:1 (v/v)).

18
[ 13910-49-1 ]
[ 151982-51-3 ]
N-[3-(N-benzyl-N-methylamino)propyl]-4-bromo-2-fluorobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With triethylamine; In dichloromethane; at 0 - 20℃; for 12h;	General procedure: A solution of N,N-disubstitutedalkyldiamine 5a-f or commercially available amine (1 eq), and triethylamine (3 eq) in 10mL of DCM was cooled at 0C. A solution of substituted benzoylchloride (1 eq) in 5mL of DCM was added slowly. The resulting mixture was stirred at room temperature overnight. The solution was evaporated under reduced pressure. An aqueous solution of 3% sodium hydroxide (20mL) was added and the mixture was stirred for 1h. The solution was extracted with DCM. The organic layer was dried over magnesium sulphate and concentrated to give an oily product. The residue was purified by thick layer chromatography (DCM:MeOH(NH3), 9:1 (v/v)) or column chromatography (DCM:MeOH(NH3), 9:1 (v/v)).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 138,p. 964 - 978

19
[ 13910-49-1 ]
[ 122-01-0 ]
[ 1327827-70-2 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine In dichloromethane at 0 - 20℃; for 12h;	28 5.1.3.18 General procedure E1 General procedure: A solution of N,N-disubstitutedalkyldiamine 5a-f or commercially available amine (1 eq), and triethylamine (3 eq) in 10mL of DCM was cooled at 0°C. A solution of substituted benzoylchloride (1 eq) in 5mL of DCM was added slowly. The resulting mixture was stirred at room temperature overnight. The solution was evaporated under reduced pressure. An aqueous solution of 3% sodium hydroxide (20mL) was added and the mixture was stirred for 1h. The solution was extracted with DCM. The organic layer was dried over magnesium sulphate and concentrated to give an oily product. The residue was purified by thick layer chromatography (DCM:MeOH(NH3), 9:1 (v/v)) or column chromatography (DCM:MeOH(NH3), 9:1 (v/v)).

20
[ 13910-49-1 ]
[ 97655-98-6 ]
[ 2226199-50-2 ]

Yield	Reaction Conditions	Operation in experiment
57.1%	With pyridine In dichloromethane at 20℃; for 48h;	4.1 General procedure for the synthesis of 9-11 General procedure: To a stirred solution of compound 5 (100mg, 0.37mmol) and pyridine (0.06mL, 0.75mmol) in CH2Cl2 (1 mL), corresponding primary amines 6-8 (0.56mmol) was added dropwise. The reaction mixture was stirred for 2d at room temperature. After the reaction was completed, the mixture was concentrated. Then water (10mL) was added to the residue and the mixture was extracted with ethyl acetate (8mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (10mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude compound. The obtained residue was purified by preparative thin-layer chromatogram to afford 9-11. a

Reference： [1]Xu, Rui; Xiao, Ganyuan; Li, Yan; Liu, Hongyan; Song, Qing; Zhang, Xiaoyu; Yang, Ziyi; Zheng, Yunxiaozhu; Tan, Zhenghuai; Deng, Yong [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1885 - 1895]

21
[ 52449-98-6 ]
[ 13910-49-1 ]
C₁₆H₂₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
101 g	With triethylamine; In 1,2-dichloro-ethane; at 5 - 35℃; for 3h;	4 Under dry conditions, 66.6 g (0.616 mol) of thionyl chloride was added dropwise to tetrahydrofurancarboxylic acid, and the temperature was controlled at 35 C for 3 hours to obtain tetrahydrofuroyl chloride, and then the temperature was controlled at 5 to 15 C, tetrahydrofuroyl chloride was added dropwise to 56.7 g (0.56 mol) of the acid-binding agent triethylamine, the organic solvent dichloroethane and N-methyl-N-benzyl-3-aminopropyldiamine 99 g ( 0.56mol) of the mixed solution, dripping, temperature control 35 C, reaction for 3 hours, adjusted to pH 8 with sodium bicarbonate solution, extracted with organic solvent, spin dry to obtain N-methyl-N-benzyl-3-acryl-tetrahydrofurancarboxamide crude product 128g, after purification to obtain refined product 101g, the yield is 65.8%

Reference： [1]Patent: CN108003141,2018,A .Location in patent: Paragraph 0032; 0038; 0052

22
[ 127-88-8 ]
[ 13910-49-1 ]
[ 39070-14-9 ]
(1-methyl-2-nitro-1H-imidazol-5-yl)methyl N,N-bis(2-chloroethyl)-N'-[3-(N''-benzyl-N''-methylamino)propyl]phosphorodiamidate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%		General procedure: To a solution of <strong>[39070-14-9](1-methyl-2-nitro-1H-imidazol-5-yl)methanol</strong> (6) (1 eq.) in freshly distilled anhydrous THF (10?mL for 3?mmol of alcohol 6) was added dropwise lithium bis(trimethylsilyl)amide (1?M in THF, 1.1 eq.) at -78?C under an inert atmosphere. The reaction mixture was stirred around 5?min?at -78?C, and a solution of bis(2-chloroethyl)phosphoramidic dichloride (8) (1.1 eq.) in THF (3.3?mmol in 10?mL), previously cooled at -78?C, was added all at once at the same temperature (T0). The reaction mixture was stirred for 15-80?min, before the addition of a solution of the appropriate amine 18-22 (2-2.2 eq.) in THF (3?mL for 5?mmol of amine) and stirring was maintained at -78?C for 5?min to 75?min. These reaction times were determined by 31P NMR monitoring for each compound. The reaction was stopped by addition of water (20?mL for 3?mmol of alcohol 6), concentrated in vacuum and then extracted with EtOAc (3?*?50?mL for 3?mmol of alcohol 6). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using an eluent gradient (EtOAc/EtOH with TEA or NH4OH) to afford compounds 23-27 as yellow to orange oils.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 158,p. 51 - 67

23
[ 13910-49-1 ]
[ 610-92-4 ]
 N¹,N⁴-bis(3-(benzyl(methyl)amino)propyl)-2,5-dihydroxyterephthalamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62.6%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; at 20℃;	General procedure: To a stirred solution of compound 4 (50 mg, 0.252 mmol), EDCI (169 mg, 0.882 mmol), HOBt (119 mg, 0.881 mmol) and triethylamine (0.176 mL, 1.26 mmol) in tetrahydrofuran (3 mL), corresponding primary amines 5-7 (0.882mmol) was added. The reaction mixture was stirred at room temperature overnight. After the reaction was completed, the mixture was concentrated. Then dichloromethane (15 mL) was added to the residue and the mixture was washed with saturated aqueous sodium bicarbonate solution (10 mL) and brine (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude compound. The obtained residue was purified by silica gel column chromatography to afford 8-10. 4.1.4.1 N1,N4-bis(3-(benzyl(methyl)amino)propyl)-2,5-dihydroxyterephthalamide (8a) Compound 8a was synthesized from intermediate 4 and 5a according to the general procedure. After purification by chromatography on silica gel using dichloromethane/acetone (1:3) as eluent, the pure product 8a was obtained as yellow oil, yield 62.6%. 1H NMR (400 MHz, CDCl3) delta 11.80 (brs, 2H), 8.76 (brs, 2H), 7.33-7.26 (m, 10H), 6.87 (s, 2H), 3.64 (s, 4H), 3.55-3.45 (m, 4H), 2.65-2.60 (m, 4H), 2.39 (s, 6H), 1.86-1.79 (m, 4H); 13C NMR (100 MHz, CDCl3) delta 168.7, 152.7, 136.9, 129.4, 128.6, 127.6, 119.2, 114.3, 62.9, 56.1, 41.8, 40.0, 24.6. ESI-MS m/z: 519.4 [M+H]+

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 6115 - 6127

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P378
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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.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 13910-49-1 ] {[proInfo.proName]}

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[ 13910-49-1 ] Synthesis Path-Downstream 1~23

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