[ CAS No. 16691-43-3 ] {[proInfo.proName]}

Name: 16691-43-3|3-Amino-1H-1,2,4-triazole-5-thiol|95%
Brand: Ambeed
SKU: A919564
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Quality Control of [ 16691-43-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 16691-43-3 ]

CAS No. :	16691-43-3	MDL No. :	MFCD00005231
Formula :	C₂H₄N₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WZUUZPAYWFIBDF-UHFFFAOYSA-N
M.W :	116.15	Pubchem ID :	2723869
Synonyms :

Calculated chemistry of [ 16691-43-3 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	28.04
TPSA :	106.39 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.12
Log Po/w (XLOGP3) :	0.12
Log Po/w (WLOGP) :	-0.32
Log Po/w (MLOGP) :	-1.42
Log Po/w (SILICOS-IT) :	0.86
Consensus Log Po/w :	-0.13

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.16
Solubility :	7.96 mg/ml ; 0.0685 mol/l
Class :	Very soluble
Log S (Ali) :	-1.91
Solubility :	1.43 mg/ml ; 0.0123 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.56
Solubility :	32.0 mg/ml ; 0.275 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.57

Safety of [ 16691-43-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 16691-43-3 ]

* 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.

Upstream synthesis route of [ 16691-43-3 ]
Downstream synthetic route of [ 16691-43-3 ]

[ 16691-43-3 ] Synthesis Path-Upstream 1~2

1
[ 142-46-1 ]
[ 16691-43-3 ]

Reference： [1] Asian Journal of Chemistry, 2011, vol. 23, # 2, p. 602 - 608
[2] European Journal of Medicinal Chemistry, 2013, vol. 64, p. 54 - 61

2
[ 108302-28-9 ]
[ 16691-43-3 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 355 - 360

[ 16691-43-3 ] Synthesis Path-Downstream 1~24

1
[ 142-46-1 ]
[ 16691-43-3 ]

Reference： [1]Chemische Berichte,1922,vol. 55,p. 13
[2]Journal of the Indian Institute of Science, Section A,1938,vol. 21,p. 51
Chemisches Zentralblatt,1938,vol. 109,p. 2933

2
[ 3034-48-8 ]
[ 16691-43-3 ]
[ 79134-07-9 ]

Reference： [1]European Journal of Medicinal Chemistry,1981,vol. 16,p. 233 - 239

3
[ 10602-37-6 ]
[ 16691-43-3 ]
[ 85599-39-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With acetic acid for 1.5h; Heating;

Reference： [1]Kuenstlinger, M.; Breitmaier, E. [Synthesis, 1983, # 1, p. 44 - 47]

4
[ 765-09-3 ]
[ 16691-43-3 ]
[ 183793-94-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In acetonitrile for 2h; Heating;

Reference： [1]White, Andrew D.; Creswell, Mark W.; Chucholowski, Alexander W.; Blankley, C. John; Wilson, Michael W.; Bousley, Richard F.; Essenburg, Arnold D.; Hamelehle, Katherine L.; Krause, Brian R.; Stanfield, Richard L.; Dominick, Mark A.; Neub, Martin [Journal of Medicinal Chemistry, 1996, vol. 39, # 22, p. 4382 - 4395]

5
[ 105-36-2 ]
[ 16691-43-3 ]
[ 352349-53-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydroxide In methanol; water at 20℃; for 2h;

Reference： [1]Chen, Qiong; Zhu, Xiao-Lei; Jiang, Li-Li; Liu, Zu-Ming; Yang, Guang-Fu [European Journal of Medicinal Chemistry, 2008, vol. 43, # 3, p. 595 - 603]

6
[ 66648-50-8 ]
[ 16691-43-3 ]
C₁₁H₁₀N₄O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In ethanol; for 2.0h;Heating / reflux;	The caffeic ethylester denoted by the chemical formula 2 10 g is dissolved in ethanol 50 ml, triazol derivate denoted by the chemical formula 3 5 g is applied, reflux stirring for 2 hours is performed and lastly it is cooled to the room temperature.After strong hydrochloric acid 1 mL is applied, it is kept cool. By filtering the sediment and drying, the caffeic acid derivative 12 g (yield 80%) is achieved. By the result of the element analysis, it shows a proportions of ?C 48.92 H 3.54 N 19.98 O 17.51; S 11.45? so that it is identified that the achieved caffeic acid derivative is the material (C11H10N403S1(278.33): C 47.47 H 3.62 N 20.13 O 17.24 S 11.52) which satisfies the chemical formula 1.

Reference： [1]Patent: US2008/319059,2008,A1 .Location in patent: Page/Page column 3

7
[ 142-46-1 ]
[ 16691-43-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water; for 3h;Reflux;	(2) NaOH (225g, 5.62mol) was dissolved in water (960mL). 2 was then added and the solution was refluxed for 3h. After cooling, the pH value of the solution was adjusted to 1 using hydrochloric acid. After that the solid was precipitated and recrystallization from methanol gave 3 as colorless crystals.

Reference： [1]Asian Journal of Chemistry,2011,vol. 23,p. 602 - 608
[2]European Journal of Medicinal Chemistry,2013,vol. 64,p. 54 - 61

8
[ 2582-30-1 ]
[ 16691-43-3 ]

Yield	Reaction Conditions	Operation in experiment
80.1%		Step 1: A mixture of <strong>[2582-30-1]aminoguanidine bicarbonate</strong> (27.78 g, 0.2 mol), ammonium thiocyanate (8.27 g, 0.24 mol), and 10 mL of distilled water was added into a 250-mL three necked flask equipped with a motor stirrer, a thermometer, and a tail gas absorption device.The resulting solution was heated to 80 C under stirring until no air bubbles were observed, and the produced water was then removed by vacuum distillation. Concentrated hydrochloric acid (27.6 mL) was added dropwise to the above mixture and kept stirring for 1 h. After that, 22 mL aqueous solution (40%) of NaOH was added dropwise, and the resulting solution was heated and refluxed for 2 h, which was then cooled to room temperature. The white gray crude product was obtained by filtration after the pH was adjusted to 1 by concentrated hydrochloric acid. Recrystallization of the crude product from water gives white pure 5-amino-1H-1,2,4-triazole-3-thiol (ATT) with a yield of 80.1%. 1H-NMR (400 MHz, DMSO) delta: 12.26 (s, 1H), 12.04 (s, 1H), 5.72 (s, 2H). IR (KBr, cm-1): 3378(m),1644(s), 1584(m), 1481(m), 1231(s), 1135(m), 1066(w), 1025(m). Elemental Analysis (%): Found (Calcd) for ATT: C, 20.72 (20.68); H, 3.45 (3.47); N, 48.22 (48.24).

Reference： [1]Journal of Coordination Chemistry,2015,vol. 68,p. 2225 - 2239

9
[ 4857-04-9 ]
[ 16691-43-3 ]
C₁₀H₁₀N₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium carbonate; sodium iodide; In acetone; at 60℃;	General procedure: To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0g) in acetone (30mL) were added sodium carbonate (1.37g, 12.92mmol), sodium iodide (129.06mg, 0.861mmol) and benzyl bromide (1.13mL, 9.47mmol) or 2-(chloromethyl)-1H-benzo[d]imidazole (1.58g, 9.47mmol). The reaction mixture was stirred at 60C for 3-6h before cooling to room temperature. Na2CO3 and NaI were removed via filtration. The residue was concentrated under vacuum and then dissolved in EtOAc. The organic layer was washed with water (2×10mL) and brine (2×20mL) and then dried over MgSO4. After removal of the solvent, the resulting residue was subjected to column chromatography, giving the corresponding products 2a and 2b. Compound 2a, white solid (1.3g), yield: 73.2%.
	With sodium carbonate; sodium iodide; In acetone; at 60℃;	General procedure: Compounds D1-D22 were prepared following the previouslyreported method [37]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 C for 3e6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue was concentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine(2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products D1-D22.
	With sodium carbonate; In acetone; at 60℃;	General procedure: Compounds A1-A20 were prepared following the previously reported method as described for A1 [1]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone was added sodium carbonate (1.37 g, 12.92 mmol) and alkyl halide (9.47 mmol). The mixture was then stirred at 60 oC for 3-6 h before cooling to room temperature. Upon completion of the reaction monitored by TLC, Na2CO3 were removed via filtration and the filtrate was evaporated under vacuum. The residue was purified by column chromatography, generating A1. 5-(((5-chlorobenzo[b]thiophen-3-yl)methyl)thio)-4H-1,2,4-triazol-3-amine, white solid, yield: 64 %.

With sodium carbonate; sodium iodide; In acetone; at 60℃;

General procedure: Compounds Q1-Q22 were synthesized following the previouslyreported method as described for the synthesis of Q1 [8]. 3-Amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) reacted with differentn-bromopropane (9.47 mmol) in the presence of sodium carbonate(1.37 g,12.92 mmol) and sodium iodide (129.06 mg, 0.861 mmol) inacetone (30 mL). Upon completion of the reaction monitored bythin-layer chromatography, Na2CO3 and NaI were removed viafiltration. The filtrate was concentrated under vacuum and thendissolved in EtOAc. The organic layer was washed with water(2 x 10 mL) and brine (2 x 20 mL), which was then dried overanhydrous MgSO4. After filtration, the solvent was removed undervacuum. The resulting residue was then purified by column chromatography,affording product Q1.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 940 - 951
[2]European Journal of Medicinal Chemistry,2019,vol. 167,p. 388 - 401
[3]Chinese Chemical Letters,2020,vol. 31,p. 418 - 422
[4]European Journal of Medicinal Chemistry,2020,vol. 202
[5]European Journal of Medicinal Chemistry,2020,vol. 203
[6]Journal of Medicinal Chemistry,2020,vol. 63,p. 15979 - 15996

10
[ 16691-43-3 ]
[ 14867-28-8 ]
3-amino-5-[3-(trimethoxysilyl)propylthio]-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.1%	Stage #1: 5-amino-3-mercapto-4H-[1,2,4]triazole With sodium methylate In methanol at 10 - 20℃; for 0.5h; Stage #2: 3-iodopropyltrimethoxysilane In methanol at 20 - 30℃; for 4h;	1-3 Synthesis of 3-amino-5-[3-(trimethoxysilyl)propylthio]-4H-1,2,4-triazole A suspension composed of 6.96 g (60 mmol) of 3-amino-5-mercapto-1,2,4-triazole and 100 ml of dehydrated methanol was cooled to 10°C, thereto was added 3.24 g (60 mmol) of sodium methoxide (solid) to form an uniform solution, followed by returning to room temperature and stirring for 30 minutes, and thereto was added dropwise a solution composed of 17.42 g (60 mmol) of 3-iodopropyltrimethoxysilane and 20 ml of dehydrated methanol at room temperature over a period of 30 minutes, followed by further stirring at from 27 to 30°C for 3 hours and 30 minutes.The reaction solution was concentrated under a reduced pressure, and 26.4 g of the resulting white viscous substance was extracted three times with 100 ml of diethyl ether, and the extract was filtered and concentrated under a reduced pressure to obtain 9.20 g (33 mmol, yield of 55.1 %) of a slightly yellow-brown colored oily substance.

Reference： [1]Current Patent Assignee: SHIKOKU CHEMICALS CORPORATION - KR2016/29029, 2016, A Location in patent: Paragraph 0389-0392; 0397

11
[ 5089-70-3 ]
[ 16691-43-3 ]
3-amino-5-[3-(triethoxysilanyl)propylthio]-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.7%	Stage #1: 5-amino-3-mercapto-4H-[1,2,4]triazole With sodium ethanolate In ethanol at 10 - 20℃; for 0.5h; Stage #2: (3-chloropropyl)triethoxysilane In ethanol at 20 - 78℃; for 6.16667h;	1-5 Synthesis of 3-amino-5-[3-(triethoxysilyl)propylthio]-1,2,4-triazole A suspension composed of 3.48 g (30 mmol) of 3-amino-5-mercapto-1,2,4-triazole and 50 ml of dehydrated ethanol was cooled to 10°C, thereto was added 10.2 g (30 mmol) of a 20% sodium ethoxide ethanol solution to form an uniform solution, followed by returning to room temperature and stirring for 30 minutes, and thereto was added dropwise a solution composed of 6.74 g (30 mmol) of 3-chloropropyltriethoxysilane and 10 ml of dehydrated ethanol at the same temperature over a period of 10 minutes, followed by further stirring at 78°C for 6 hours.The reaction solution was concentrated under a reduced pressure, and 10.8 g of the resulting white viscous substance was extracted three times with 40 ml of diethyl ether, and the extract was filtered and concentrated under a reduced pressure to obtain 7.8 g (25 mmol, yield of 85.7%) of slightly yellow-brown colored crystals.

Reference： [1]Current Patent Assignee: SHIKOKU CHEMICALS CORPORATION - KR2016/29029, 2016, A Location in patent: Paragraph 0407-0410; 0416

12
[ 16691-43-3 ]
[ 20443-99-6 ]
[ 303150-34-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ethanol; water at 70℃; for 0.333333h;

Reference： [1]Helgren, Travis R.; Chen, Congling; Wangtrakuldee, Phumvadee; Edwards, Thomas E.; Staker, Bart L.; Abendroth, Jan; Sankaran, Banumathi; Housley, Nicole A.; Myler, Peter J.; Audia, Jonathon P.; Horn, James R.; Hagen, Timothy J. [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 3, p. 813 - 824]

13
[ 603-67-8 ]
[ 16691-43-3 ]
7-mercapto-3-nitro-1,2,4-triazolo[5,1-c]-1,2,4-triazin-4(1H)-one sodium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1 : Diazotization of compound (B): A solution (solution [1], herein after) was prepared of 5.8 g (0.05 ) of 5-amino-3-mercapto-1 ,2,4-triazole in 6.7 ml of nitric acid (15 M) and 12 ml of water. Said solution [1] was refrigerated to - 7C . Then a 40% sodium nitrite solution was added to the solution [1] in portions of 0.5 mL to obtain a total amount of sodium nitrite equal to 3.8 g in the mixture. Step 2: Condensation of diazonium compound with an a-nitroester: To the resulting diazonium salt of step 1 , 8.54 ml of diethyl nitromaionate was added. After holding for five minutes, a cooled solution of sodium hydroxide was slowly added dropwise to the reaction mixture until the pH was between pH 9 and pH 10 (solution [2], herein after). The resulting solution [2] was stirred at 0C for 1 hour and at room temperature for 2 hours.
		A solution (solution [1], herein after) was prepared of 5.8 g (0.05 M) of 5-amino-3-mercapto-1 ,2,4-triazole in 6.7 ml of nitric acid (15 M) and 12 ml of water. Said solution [1] was refrigerated to - 7C . Then a 40% sodium nitrite solution was added to the solution [1] in portions of 0.5 mL to obtain a total amount of sodium nitrite equal to 3.8 g in the mixture. To the resulting diazonium salt of step 1 , 8.54 ml of <strong>[603-67-8]diethyl nitromalonate</strong> was added. After holding for five minutes, a cooled solution of sodium hydroxide was slowly added dropwise to the reaction mixture until the pH was between pH 9 and pH 10 (solution [2], herein after). The resulting solution [2] was stirred at 0C for 1 hour and at room temperature for 2 hours.

Reference： [1]Patent: WO2017/144709,2017,A1 .Location in patent: Page/Page column 24
[2]Patent: WO2017/144708,2017,A2 .Location in patent: Page/Page column 23-24

14
[ 540-54-5 ]
[ 16691-43-3 ]
[ 51493-17-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. General method for the synthesis of A1-A20 General procedure: Compounds A1-A20 were prepared following the previouslyreported method [43]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 °C for 3-6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue wasconcentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine (2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products A1-A20.
	With sodium carbonate In acetone at 20℃;	1.1 (1) Preparation of Compound Q 1 g (about 8.61 mmol) of 2-amino-5-mercapto-1,2,4-triazole and1.37 g (about 12.92 mmoL) of sodium carbonate was added to the reaction flask,Then add about 20 mL of acetone and slowly add 909.73 μL (about 10.33 mmoL) of chloropropane.The reaction was carried out at room temperature, and the reaction was monitored by thin layer chromatography TLC.After completion of the reaction, the mixture was directly filtered under suction, and the filtrate was subjected to column chromatography (dichloromethane:methanol = 20:1) to afford pure compound Q. Calculated by measurement:Compound Q is a white solid with a yield of about 76%.
	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. General method for the synthesis of D1-D22 General procedure: Compounds D1-D22 were prepared following the previouslyreported method [37]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 C for 3e6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue was concentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine(2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products D1-D22.

	With sodium carbonate In acetone at 60℃;	4.2. General method for the synthesis of A1-A20 General procedure: Compounds A1-A20 were prepared following the previously reported method as described for A1 [1]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone was added sodium carbonate (1.37 g, 12.92 mmol) and alkyl halide (9.47 mmol). The mixture was then stirred at 60 oC for 3-6 h before cooling to room temperature. Upon completion of the reaction monitored by TLC, Na2CO3 were removed via filtration and the filtrate was evaporated under vacuum. The residue was purified by column chromatography, generating A1. 5-(((5-chlorobenzo[b]thiophen-3-yl)methyl)thio)-4H-1,2,4-triazol-3-amine, white solid, yield: 64 %.
	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. The general method for the synthesis of Q1-Q22 General procedure: Compounds Q1-Q22 were synthesized following the previouslyreported method as described for the synthesis of Q1 [8]. 3-Amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) reacted with differentn-bromopropane (9.47 mmol) in the presence of sodium carbonate(1.37 g,12.92 mmol) and sodium iodide (129.06 mg, 0.861 mmol) inacetone (30 mL). Upon completion of the reaction monitored bythin-layer chromatography, Na2CO3 and NaI were removed viafiltration. The filtrate was concentrated under vacuum and thendissolved in EtOAc. The organic layer was washed with water(2 x 10 mL) and brine (2 x 20 mL), which was then dried overanhydrous MgSO4. After filtration, the solvent was removed undervacuum. The resulting residue was then purified by column chromatography,affording product Q1.
	With sodium carbonate; sodium iodide In acetone Reflux;
	With sodium carbonate In acetone at 60℃;

Reference： [1]Li, Zhong-Rui; Wang, Shuai; Yang, Linlin; Yuan, Xiao-Han; Suo, Feng-Zhi; Yu, Bin; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2019, vol. 166, p. 432 - 444]
[2]Current Patent Assignee: ZHENGZHOU UNIVERSITY - CN109293664, 2019, A Location in patent: Paragraph 0053; 0057
[3]Wang, Shuai; Li, Zhong-Rui; Suo, Feng-Zhi; Yuan, Xiao-Han; Yu, Bin; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2019, vol. 167, p. 388 - 401]
[4]Wang, Shuai; Shen, Dandan; Zhao, Lijie; Yuan, Xiaohan; Cheng, Jialing; Yu, Bin; Zheng, Yichao; Liu, Hongmin [Chinese Chemical Letters, 2020, vol. 31, # 2, p. 418 - 422]
[5]Shi, Xiao-Jing; Wang, Shuai; Li, Xiao-Jing; Yuan, Xiao-Han; Cao, Li-Juan; Yu, Bin; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2020, vol. 203]
[6]Wang, Shuai; Wang, Sai-Qi; Teng, Qiu-Xu; Yang, Linlin; Lei, Zi-Ning; Yuan, Xiao-Han; Huo, Jun-Feng; Chen, Xiao-Bing; Wang, Mengru; Yu, Bin; Chen, Zhe-Sheng; Liu, Hong-Min [Journal of Medicinal Chemistry, 2020, vol. 63, # 24, p. 15979 - 15996]
[7]Wang, Shuai; Wang, Sai-Qi; Teng, Qiu-Xu; Lei, Zi-Ning; Chen, Zhe-Sheng; Chen, Xiao-Bing; Liu, Hong-Min; Yu, Bin [Journal of Medicinal Chemistry, 2021, vol. 64, # 21, p. 16187 - 16204]

15
[ 624-65-7 ]
[ 16691-43-3 ]
[ 53918-44-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. General method for the synthesis of A1-A20 General procedure: Compounds A1-A20 were prepared following the previouslyreported method [43]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 °C for 3-6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue wasconcentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine (2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products A1-A20.
	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. General method for the synthesis of D1-D22 General procedure: Compounds D1-D22 were prepared following the previouslyreported method [37]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 C for 3e6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue was concentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine(2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products D1-D22.
	With sodium carbonate In acetone at 60℃;	4.2. General method for the synthesis of A1-A20 General procedure: Compounds A1-A20 were prepared following the previously reported method as described for A1 [1]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone was added sodium carbonate (1.37 g, 12.92 mmol) and alkyl halide (9.47 mmol). The mixture was then stirred at 60 oC for 3-6 h before cooling to room temperature. Upon completion of the reaction monitored by TLC, Na2CO3 were removed via filtration and the filtrate was evaporated under vacuum. The residue was purified by column chromatography, generating A1. 5-(((5-chlorobenzo[b]thiophen-3-yl)methyl)thio)-4H-1,2,4-triazol-3-amine, white solid, yield: 64 %.

	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. The general method for the synthesis of Q1-Q22 General procedure: Compounds Q1-Q22 were synthesized following the previouslyreported method as described for the synthesis of Q1 [8]. 3-Amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) reacted with differentn-bromopropane (9.47 mmol) in the presence of sodium carbonate(1.37 g,12.92 mmol) and sodium iodide (129.06 mg, 0.861 mmol) inacetone (30 mL). Upon completion of the reaction monitored bythin-layer chromatography, Na2CO3 and NaI were removed viafiltration. The filtrate was concentrated under vacuum and thendissolved in EtOAc. The organic layer was washed with water(2 x 10 mL) and brine (2 x 20 mL), which was then dried overanhydrous MgSO4. After filtration, the solvent was removed undervacuum. The resulting residue was then purified by column chromatography,affording product Q1.
	With sodium carbonate In acetone at 60℃;
	With sodium carbonate; sodium iodide In acetone Reflux;

Reference： [1]Li, Zhong-Rui; Wang, Shuai; Yang, Linlin; Yuan, Xiao-Han; Suo, Feng-Zhi; Yu, Bin; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2019, vol. 166, p. 432 - 444]
[2]Wang, Shuai; Li, Zhong-Rui; Suo, Feng-Zhi; Yuan, Xiao-Han; Yu, Bin; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2019, vol. 167, p. 388 - 401]
[3]Wang, Shuai; Shen, Dandan; Zhao, Lijie; Yuan, Xiaohan; Cheng, Jialing; Yu, Bin; Zheng, Yichao; Liu, Hongmin [Chinese Chemical Letters, 2020, vol. 31, # 2, p. 418 - 422]
[4]Shi, Xiao-Jing; Wang, Shuai; Li, Xiao-Jing; Yuan, Xiao-Han; Cao, Li-Juan; Yu, Bin; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2020, vol. 203]
[5]Wang, Shuai; Ma, Xu-Bin; Yuan, Xiao-Han; Yu, Bin; Xu, Yi-Chao; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2020, vol. 203] Wang, Shuai; Wang, Sai-Qi; Teng, Qiu-Xu; Lei, Zi-Ning; Chen, Zhe-Sheng; Chen, Xiao-Bing; Liu, Hong-Min; Yu, Bin [Journal of Medicinal Chemistry, 2021, vol. 64, # 21, p. 16187 - 16204]
[6]Wang, Shuai; Wang, Sai-Qi; Teng, Qiu-Xu; Yang, Linlin; Lei, Zi-Ning; Yuan, Xiao-Han; Huo, Jun-Feng; Chen, Xiao-Bing; Wang, Mengru; Yu, Bin; Chen, Zhe-Sheng; Liu, Hong-Min [Journal of Medicinal Chemistry, 2020, vol. 63, # 24, p. 15979 - 15996]

16
[ 16691-43-3 ]
[ 5911-08-0 ]
5-((cyclopropylmethyl)thio)-4H-1,2,4-triazol-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. General method for the synthesis of A1-A20 General procedure: Compounds A1-A20 were prepared following the previouslyreported method [43]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 °C for 3-6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue wasconcentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine (2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products A1-A20.
	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. General method for the synthesis of D1-D22 General procedure: Compounds D1-D22 were prepared following the previouslyreported method [37]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 C for 3e6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue was concentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine(2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products D1-D22.
	With sodium carbonate In acetone at 60℃;	4.2. General method for the synthesis of A1-A20 General procedure: Compounds A1-A20 were prepared following the previously reported method as described for A1 [1]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone was added sodium carbonate (1.37 g, 12.92 mmol) and alkyl halide (9.47 mmol). The mixture was then stirred at 60 oC for 3-6 h before cooling to room temperature. Upon completion of the reaction monitored by TLC, Na2CO3 were removed via filtration and the filtrate was evaporated under vacuum. The residue was purified by column chromatography, generating A1. 5-(((5-chlorobenzo[b]thiophen-3-yl)methyl)thio)-4H-1,2,4-triazol-3-amine, white solid, yield: 64 %.

	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. The general method for the synthesis of Q1-Q22 General procedure: Compounds Q1-Q22 were synthesized following the previouslyreported method as described for the synthesis of Q1 [8]. 3-Amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) reacted with differentn-bromopropane (9.47 mmol) in the presence of sodium carbonate(1.37 g,12.92 mmol) and sodium iodide (129.06 mg, 0.861 mmol) inacetone (30 mL). Upon completion of the reaction monitored bythin-layer chromatography, Na2CO3 and NaI were removed viafiltration. The filtrate was concentrated under vacuum and thendissolved in EtOAc. The organic layer was washed with water(2 x 10 mL) and brine (2 x 20 mL), which was then dried overanhydrous MgSO4. After filtration, the solvent was removed undervacuum. The resulting residue was then purified by column chromatography,affording product Q1.
	With sodium carbonate; sodium iodide In acetone Reflux;

17
[ 16691-43-3 ]
[ 352-11-4 ]
[ 714203-98-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. General method for the synthesis of A1-A20 General procedure: Compounds A1-A20 were prepared following the previouslyreported method [43]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 °C for 3-6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue wasconcentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine (2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products A1-A20.
	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. General method for the synthesis of D1-D22 General procedure: Compounds D1-D22 were prepared following the previouslyreported method [37]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 C for 3e6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue was concentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine(2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products D1-D22.
	Stage #1: 5-amino-3-mercapto-4H-[1,2,4]triazole With potassium carbonate In acetone for 0.0833333h; Stage #2: 1-chloromethyl-4-fluorobenzene In acetone at 50℃;	Synthesis of variedly substituted 5-(benzylthio)-4H-1,2,4-triazol-3-amine (13a-j) General procedure: To a solution of 5-amino-4H-1,2,4-triazole-3-thiol 11 (230 mg, 0.002 mol) in 10 ml of acetone, 2 eq. K2CO3 was added. Reaction mixture was kept on stirring. After 5 minutes, variedly substituted benzyl chlorides (12a-j) were added into the reaction mixture. Further reaction mixture was left on stirring for 24 hours at 50°C. TLC confirmed the formation of product. After completion of reaction, the mixture was filtered to remove K2CO3 and concentrated. Obtained crude product was dried and recrystallized in methanol to afford the pure product 13a-j.

	With sodium carbonate In acetone at 60℃;	4.2. General method for the synthesis of A1-A20 General procedure: Compounds A1-A20 were prepared following the previously reported method as described for A1 [1]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone was added sodium carbonate (1.37 g, 12.92 mmol) and alkyl halide (9.47 mmol). The mixture was then stirred at 60 oC for 3-6 h before cooling to room temperature. Upon completion of the reaction monitored by TLC, Na2CO3 were removed via filtration and the filtrate was evaporated under vacuum. The residue was purified by column chromatography, generating A1. 5-(((5-chlorobenzo[b]thiophen-3-yl)methyl)thio)-4H-1,2,4-triazol-3-amine, white solid, yield: 64 %.
	With sodium carbonate In acetone at 60℃;
	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. The general method for the synthesis of Q1-Q22 General procedure: Compounds Q1-Q22 were synthesized following the previouslyreported method as described for the synthesis of Q1 [8]. 3-Amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) reacted with differentn-bromopropane (9.47 mmol) in the presence of sodium carbonate(1.37 g,12.92 mmol) and sodium iodide (129.06 mg, 0.861 mmol) inacetone (30 mL). Upon completion of the reaction monitored bythin-layer chromatography, Na2CO3 and NaI were removed viafiltration. The filtrate was concentrated under vacuum and thendissolved in EtOAc. The organic layer was washed with water(2 x 10 mL) and brine (2 x 20 mL), which was then dried overanhydrous MgSO4. After filtration, the solvent was removed undervacuum. The resulting residue was then purified by column chromatography,affording product Q1.
	With sodium carbonate; sodium iodide In acetone Reflux;

Reference： [1]Li, Zhong-Rui; Wang, Shuai; Yang, Linlin; Yuan, Xiao-Han; Suo, Feng-Zhi; Yu, Bin; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2019, vol. 166, p. 432 - 444]
[2]Wang, Shuai; Li, Zhong-Rui; Suo, Feng-Zhi; Yuan, Xiao-Han; Yu, Bin; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2019, vol. 167, p. 388 - 401]
[3]Singh, Pankaj Kumar; Chaudhari, Dasharath; Jain, Sanyog; Silakari, Om [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 13, p. 1565 - 1571]
[4]Wang, Shuai; Shen, Dandan; Zhao, Lijie; Yuan, Xiaohan; Cheng, Jialing; Yu, Bin; Zheng, Yichao; Liu, Hongmin [Chinese Chemical Letters, 2020, vol. 31, # 2, p. 418 - 422]
[5]Huo, Jin-ling; Liu, Hong-Min; Lu, Nan; Wang, Shuai; Yuan, Xiao-Han [European Journal of Medicinal Chemistry, 2020, vol. 202] Wang, Shuai; Wang, Sai-Qi; Teng, Qiu-Xu; Lei, Zi-Ning; Chen, Zhe-Sheng; Chen, Xiao-Bing; Liu, Hong-Min; Yu, Bin [Journal of Medicinal Chemistry, 2021, vol. 64, # 21, p. 16187 - 16204]
[6]Shi, Xiao-Jing; Wang, Shuai; Li, Xiao-Jing; Yuan, Xiao-Han; Cao, Li-Juan; Yu, Bin; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2020, vol. 203]
[7]Wang, Shuai; Wang, Sai-Qi; Teng, Qiu-Xu; Yang, Linlin; Lei, Zi-Ning; Yuan, Xiao-Han; Huo, Jun-Feng; Chen, Xiao-Bing; Wang, Mengru; Yu, Bin; Chen, Zhe-Sheng; Liu, Hong-Min [Journal of Medicinal Chemistry, 2020, vol. 63, # 24, p. 15979 - 15996]

18
[ 2014-83-7 ]
[ 16691-43-3 ]
5-((2,6-dichlorobenzyl)thio)-4H-1,2,4-triazol-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; sodium iodide; In acetone; at 60℃;	General procedure: Compounds A1-A20 were prepared following the previouslyreported method [43]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 C for 3-6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue wasconcentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine (2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products A1-A20.
	With sodium carbonate; sodium iodide; In acetone; at 60℃;	General procedure: Compounds D1-D22 were prepared following the previouslyreported method [37]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 C for 3e6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue was concentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine(2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products D1-D22.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 166,p. 432 - 444
[2]European Journal of Medicinal Chemistry,2019,vol. 167,p. 388 - 401
[3]European Journal of Medicinal Chemistry,2020,vol. 202
[4]European Journal of Medicinal Chemistry,2020,vol. 203

19
[ 939-99-1 ]
[ 16691-43-3 ]
5-((4-(trifluoromethyl)benzyl)thio)-4H-1,2,4-triazol-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. General method for the synthesis of A1-A20 General procedure: Compounds A1-A20 were prepared following the previouslyreported method [43]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 °C for 3-6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue wasconcentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine (2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products A1-A20.
	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. General method for the synthesis of D1-D22 General procedure: Compounds D1-D22 were prepared following the previouslyreported method [37]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 C for 3e6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue was concentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine(2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products D1-D22.
	With sodium carbonate In acetone at 60℃;	4.2. General method for the synthesis of A1-A20 General procedure: Compounds A1-A20 were prepared following the previously reported method as described for A1 [1]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone was added sodium carbonate (1.37 g, 12.92 mmol) and alkyl halide (9.47 mmol). The mixture was then stirred at 60 oC for 3-6 h before cooling to room temperature. Upon completion of the reaction monitored by TLC, Na2CO3 were removed via filtration and the filtrate was evaporated under vacuum. The residue was purified by column chromatography, generating A1. 5-(((5-chlorobenzo[b]thiophen-3-yl)methyl)thio)-4H-1,2,4-triazol-3-amine, white solid, yield: 64 %.

	With sodium carbonate In acetone at 60℃;
	With sodium carbonate; sodium iodide In acetone at 60℃;	4.2. The general method for the synthesis of Q1-Q22 General procedure: Compounds Q1-Q22 were synthesized following the previouslyreported method as described for the synthesis of Q1 [8]. 3-Amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) reacted with differentn-bromopropane (9.47 mmol) in the presence of sodium carbonate(1.37 g,12.92 mmol) and sodium iodide (129.06 mg, 0.861 mmol) inacetone (30 mL). Upon completion of the reaction monitored bythin-layer chromatography, Na2CO3 and NaI were removed viafiltration. The filtrate was concentrated under vacuum and thendissolved in EtOAc. The organic layer was washed with water(2 x 10 mL) and brine (2 x 20 mL), which was then dried overanhydrous MgSO4. After filtration, the solvent was removed undervacuum. The resulting residue was then purified by column chromatography,affording product Q1.
	With sodium carbonate; sodium iodide In acetone Reflux;

Reference： [1]Li, Zhong-Rui; Wang, Shuai; Yang, Linlin; Yuan, Xiao-Han; Suo, Feng-Zhi; Yu, Bin; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2019, vol. 166, p. 432 - 444]
[2]Wang, Shuai; Li, Zhong-Rui; Suo, Feng-Zhi; Yuan, Xiao-Han; Yu, Bin; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2019, vol. 167, p. 388 - 401]
[3]Wang, Shuai; Shen, Dandan; Zhao, Lijie; Yuan, Xiaohan; Cheng, Jialing; Yu, Bin; Zheng, Yichao; Liu, Hongmin [Chinese Chemical Letters, 2020, vol. 31, # 2, p. 418 - 422]
[4]Huo, Jin-ling; Liu, Hong-Min; Lu, Nan; Wang, Shuai; Yuan, Xiao-Han [European Journal of Medicinal Chemistry, 2020, vol. 202] Wang, Shuai; Ma, Xu-Bin; Yuan, Xiao-Han; Yu, Bin; Xu, Yi-Chao; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2020, vol. 203] Wang, Shuai; Wang, Sai-Qi; Teng, Qiu-Xu; Lei, Zi-Ning; Chen, Zhe-Sheng; Chen, Xiao-Bing; Liu, Hong-Min; Yu, Bin [Journal of Medicinal Chemistry, 2021, vol. 64, # 21, p. 16187 - 16204]
[5]Shi, Xiao-Jing; Wang, Shuai; Li, Xiao-Jing; Yuan, Xiao-Han; Cao, Li-Juan; Yu, Bin; Liu, Hong-Min [European Journal of Medicinal Chemistry, 2020, vol. 203]
[6]Wang, Shuai; Wang, Sai-Qi; Teng, Qiu-Xu; Yang, Linlin; Lei, Zi-Ning; Yuan, Xiao-Han; Huo, Jun-Feng; Chen, Xiao-Bing; Wang, Mengru; Yu, Bin; Chen, Zhe-Sheng; Liu, Hong-Min [Journal of Medicinal Chemistry, 2020, vol. 63, # 24, p. 15979 - 15996]

20
[ 21742-00-7 ]
[ 16691-43-3 ]
5-((2-(trifluoromethyl)benzyl)thio)-4H-1,2,4-triazol-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; sodium iodide; In acetone; at 60℃;	General procedure: Compounds A1-A20 were prepared following the previouslyreported method [43]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 C for 3-6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue wasconcentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine (2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products A1-A20.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 166,p. 432 - 444
[2]European Journal of Medicinal Chemistry,2020,vol. 202

21
[ 104-52-9 ]
[ 16691-43-3 ]
5-((3-phenylpropyl)thio)-4H-1,2,4-triazol-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; sodium iodide; In acetone; at 60℃;	General procedure: Compounds A1-A20 were prepared following the previouslyreported method [43]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 C for 3-6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue wasconcentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine (2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products A1-A20.
	With sodium carbonate; sodium iodide; In acetone; at 60℃;	General procedure: Compounds D1-D22 were prepared following the previouslyreported method [37]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 C for 3e6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue was concentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine(2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products D1-D22.
	With sodium carbonate; In acetone; at 60℃;	General procedure: Compounds A1-A20 were prepared following the previously reported method as described for A1 [1]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone was added sodium carbonate (1.37 g, 12.92 mmol) and alkyl halide (9.47 mmol). The mixture was then stirred at 60 oC for 3-6 h before cooling to room temperature. Upon completion of the reaction monitored by TLC, Na2CO3 were removed via filtration and the filtrate was evaporated under vacuum. The residue was purified by column chromatography, generating A1. 5-(((5-chlorobenzo[b]thiophen-3-yl)methyl)thio)-4H-1,2,4-triazol-3-amine, white solid, yield: 64 %.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 166,p. 432 - 444
[2]European Journal of Medicinal Chemistry,2019,vol. 167,p. 388 - 401
[3]Chinese Chemical Letters,2020,vol. 31,p. 418 - 422

22
[ 2994-69-6 ]
[ 16691-43-3 ]
5-((3-chloro-4-fluorobenzyl)thio)-4H-1,2,4-triazol-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; sodium iodide; In acetone; at 60℃;	General procedure: Compounds D1-D22 were prepared following the previouslyreported method [37]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone (30 mL) were added sodiumcarbonate (1.37 g, 12.92 mmol), sodium iodide (129.06 mg,0.861 mmol) and alkyl halide (9.47 mmol). The reaction mixturewas stirred at 60 C for 3e6 h before cooling to room temperature.Na2CO3 and NaI were removed via filtration. The residue was concentrated under vacuum and then dissolved in EtOAc. Theorganic layer was washed with water (2 x 10 mL) and brine(2 x 20 mL) and then dried over anhydrous MgSO4. After removal ofthe solvent, the resulting residue was subjected to column chromatography,giving the corresponding products D1-D22.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 167,p. 388 - 401

23
[ 94-99-5 ]
[ 16691-43-3 ]
[ 303150-34-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5-amino-3-mercapto-4H-[1,2,4]triazole With potassium carbonate In acetone for 0.0833333h; Stage #2: 2,4-Dichlorobenzyl chloride In acetone at 50℃;	Synthesis of variedly substituted 5-(benzylthio)-4H-1,2,4-triazol-3-amine (13a-j) General procedure: To a solution of 5-amino-4H-1,2,4-triazole-3-thiol 11 (230 mg, 0.002 mol) in 10 ml of acetone, 2 eq. K2CO3 was added. Reaction mixture was kept on stirring. After 5 minutes, variedly substituted benzyl chlorides (12a-j) were added into the reaction mixture. Further reaction mixture was left on stirring for 24 hours at 50°C. TLC confirmed the formation of product. After completion of reaction, the mixture was filtered to remove K2CO3 and concentrated. Obtained crude product was dried and recrystallized in methanol to afford the pure product 13a-j.

Reference： [1]Singh, Pankaj Kumar; Chaudhari, Dasharath; Jain, Sanyog; Silakari, Om [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 13, p. 1565 - 1571]

24
[ 2530-83-8 ]
[ 16691-43-3 ]
C₁₁H₂₄N₄O₅SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 65℃; for 18h;	In a first step, 3.36 g (28.4 mmol) 5-amino-4H-1 ,2,4-triazole-3-thiol (azole compound of formula (III), wherein X denotes NH2 and Y denotes NH) were suspended in 70 ml meth- anol and an azole suspension was obtained. (0215) In a second step, a solution made by dissolving 6.91 g (28.4 mmol) 3- glycidoxypropyltrimethoxysilane (silane compound of formula (IV), wherein R denotes CH3 and n is 3) in 20 ml methanol was added to the azole suspension. As a result, a re- action suspension was obtained. (0216) In a third step, the reaction suspension was heated to reflux (temperature approximately 65 C) for 18 hours. During that time the suspension turned into a clear solution indicat- ing that the azole compound was fully used up. Afterwards, the solvent (methanol) was removed and approximately 10 g (yield 100%) of a yellow, highly viscous substance were obtained as product, primarily being the azole silane compound of formula (lb). The thus obtained product was free of any halides and utilized without further purification. (0217) 1H NMR: (400 MHz, DMSO-d6) d 6.03 (s, 2H), 5.33 - 5.08 (m, 1 H), 3.87 - 3.75 (m, 1 H), 3.54 - 3.25 (m, 13H), 3.22 - 3.08 (m, 1 H), 2.97 {dd, J = 13.3, 7.0 Hz, 1 H), 1.55 (dddd, J = 12.7, 1 1.1 , 6.6, 3.5 Hz, 2H), 0.67 - 0.50 (m, 2H) ESI-MS: m/z: 352.12 (100.0%), 353.13 (11.9%) (0218) Both NMR and ESI-MS confirm the presence of the azole silane compound of formula (lb). The theoretical molar mass is 352 g/mol.

Reference： [1]Patent: WO2019/243180,2019,A1 .Location in patent: Page/Page column 22; 23

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[ CAS No. 16691-43-3 ] {[proInfo.proName]}

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[ 16691-43-3 ] Synthesis Path-Upstream 1~2

[ 16691-43-3 ] Synthesis Path-Downstream 1~24

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Amines

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Triazoles

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