[ CAS No. 4922-98-9 ] {[proInfo.proName]}

Name: 4922-98-9|5-Phenyl-1H-1,2,4-triazol-3-amine|97%
Brand: Ambeed
SKU: A236620
Price: 38.0 USD
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Quality Control of [ 4922-98-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 4922-98-9 ]

Product Details of [ 4922-98-9 ]

CAS No. :	4922-98-9	MDL No. :	MFCD00086332
Formula :	C₈H₈N₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GHUDJFJZFUVPIQ-UHFFFAOYSA-N
M.W :	160.18	Pubchem ID :	95778
Synonyms :

Calculated chemistry of [ 4922-98-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	46.22
TPSA :	67.59 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) :	-6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.01
Log Po/w (XLOGP3) :	1.53
Log Po/w (WLOGP) :	1.06
Log Po/w (MLOGP) :	1.17
Log Po/w (SILICOS-IT) :	1.35
Consensus Log Po/w :	1.22

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.41
Solubility :	0.624 mg/ml ; 0.0039 mol/l
Class :	Soluble
Log S (Ali) :	-2.56
Solubility :	0.443 mg/ml ; 0.00277 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.01
Solubility :	0.157 mg/ml ; 0.000979 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.86

Safety of [ 4922-98-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4922-98-9 ]

* 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 [ 4922-98-9 ]
Downstream synthetic route of [ 4922-98-9 ]

[ 4922-98-9 ] Synthesis Path-Upstream 1~5

1
[ 3679-92-3 ]
[ 4922-98-9 ]

Yield	Reaction Conditions	Operation in experiment
70.1%	at 110℃; for 6 h;	The N-benzamido guanidine (4.76 g, 26.7 mmol) obtained in Step 3 - 1 was added to 40 mL of water and heated under reflux at 110 ° C. for 6 hours. After completion of the reaction, the reaction solution was distilled off under reduced pressure to obtain 3-phenyl-1H-1,2,4-triazole-5-amine (3.0 g, 18.7 mmol, yield 70.1percent)

Reference： [1] Patent: JP6099045, 2017, B2, . Location in patent: Paragraph 0064
[2] Journal of Medicinal Chemistry, 1996, vol. 39, # 15, p. 3019 - 3029
[3] Bioorganic Chemistry, 2013, vol. 50, p. 34 - 40
[4] European Journal of Medicinal Chemistry, 2016, vol. 113, p. 11 - 27
[5] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 774 - 789

2
[ 3679-92-3 ]
[ 4922-98-9 ]

Reference： [1] Tetrahedron Letters, 2009, vol. 50, # 18, p. 2124 - 2128
[2] Heterocycles, 2007, vol. 71, # 2, p. 429 - 436
[3] Tetrahedron, 2007, vol. 63, # 52, p. 12888 - 12895
[4] European Journal of Medicinal Chemistry, 2013, vol. 67, p. 325 - 334
[5] Bioorganic Chemistry, 2018, vol. 80, p. 361 - 374

3
[ 613-94-5 ]
[ 4922-98-9 ]

Reference： [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 15, p. 3019 - 3029
[2] European Journal of Medicinal Chemistry, 2013, vol. 67, p. 325 - 334
[3] European Journal of Medicinal Chemistry, 2016, vol. 113, p. 11 - 27
[4] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 774 - 789

4
[ 98-88-4 ]
[ 4922-98-9 ]

Reference： [1] European Journal of Medicinal Chemistry, 2013, vol. 67, p. 325 - 334
[2] Patent: JP6099045, 2017, B2,
[3] Bioorganic Chemistry, 2018, vol. 80, p. 361 - 374

5
[ 65-85-0 ]
[ 4922-98-9 ]

Reference： [1] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 774 - 789

[ 4922-98-9 ] Synthesis Path-Downstream 1~88

1
[ 517-23-7 ]
[ 4922-98-9 ]
[ 74258-83-6 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 927 - 937

2
[ 13218-13-8 ]
[ 4922-98-9 ]
[ 99777-32-9 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 576 - 582
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 682 - 688

3
[ 626-35-7 ]
[ 4922-98-9 ]
[ 83809-89-6 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1980,p. 974 - 978
Khimiya Geterotsiklicheskikh Soedinenii,1980,vol. 16,p. 1283 - 1298

4
[ 14090-88-1 ]
[ 4922-98-9 ]
[ 87253-63-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 735 - 751

5
[ 4428-98-2 ]
[ 4922-98-9 ]
[ 28610-03-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 1121 - 1123

6
[ 34461-00-2 ]
[ 4922-98-9 ]
[ 107753-08-2 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1986,vol. 22,p. 543 - 546
Khimiya Geterotsiklicheskikh Soedinenii,1986,vol. 22,p. 662 - 665

7
[ 4922-98-9 ]
[ 51254-62-7 ]
(Z)-2-Nitro-3-(5-phenyl-2H-[1,2,4]triazol-3-ylamino)-acrylic acid ethyl ester [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1986,vol. 20,p. 113 - 117
Khimiko-Farmatsevticheskii Zhurnal,1986,vol. 20,p. 178 - 182

8
[ 4922-98-9 ]
[ 34461-00-2 ]
[ 105411-96-9 ]

Reference： [1]Pharmaceutical Chemistry Journal,1986,vol. 20,p. 550 - 554
Khimiko-Farmatsevticheskii Zhurnal,1986,vol. 20,p. 947 - 952
[2]Pharmaceutical Chemistry Journal,1990,vol. 24,p. 52 - 54
Khimiko-Farmatsevticheskii Zhurnal,1990,vol. 24,p. 39 - 40

9
[ 4922-98-9 ]
[ 556-61-6 ]
[ 168893-24-1 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3019 - 3029

10
[ 3679-92-3 ]
[ 4922-98-9 ]

Yield	Reaction Conditions	Operation in experiment
70.1%	In water; at 110℃; for 6h;	The N-benzamido guanidine (4.76 g, 26.7 mmol) obtained in Step 3 - 1 was added to 40 mL of water and heated under reflux at 110 ° C. for 6 hours. After completion of the reaction, the reaction solution was distilled off under reduced pressure to obtain 3-phenyl-1H-1,2,4-triazole-5-amine (3.0 g, 18.7 mmol, yield 70.1percent)
	In water; at 180℃;Microwave irradiation; Green chemistry;	General procedure: Initially, amidoguanidines (7) were prepared via the reaction of substituted benzoyl chloride (5) (10 mmol) and aminoguanidine hydrochloride (6) (20 mmol). The obtained intermediates (7) were then treated with microwave irradiation power (100 W) for 8-15 min in water to generate 5-amino-1,2,4-triazoles (8) [18] . Subsequently, 5-amino-1,2,4-triazoles (8) (3 mmol) were reacted with ethoxycarbonyl isothiocyanate (3.3 mmol) in anhydrous DMF (4 ml) at room temperature, leading to formation of thiourea derivatives (9).
	With sodium hydroxide; In water; at 100℃; for 6h;	General procedure: A solution of S-methylisothiourea hemisulfate salt (22mmol), appropriate hydrazide (22mmol), and water (35mL) was refluxed for 6h. The solvent was concentrated under reduced pressure and the residue was washed with ethanol (3×10mL). The resulting solid was poured into 10mL of 10percent NaOH and heated to reflux for additional 6h. The reaction was cooled to room temperature and adjusted to pH 5 using 1N HCl. The precipitate was filtered, washed with cold water and dried. Following general procedure A, compound 11c was isolated as a white solid. Yield 82percent, mp=233?234°C. 1H NMR (200MHz, DMSO-d6) delta: 12.58 (br s, 1H); 7.97?7.85 (m, 2H); 7.62?7.35 (m, 3H); 5.97 (br s, 2H)

Reference： [1]Patent: JP6099045,2017,B2 .Location in patent: Paragraph 0064
[2]Journal of Medicinal Chemistry,1996,vol. 39,p. 3019 - 3029
[3]Bioorganic Chemistry,2013,vol. 50,p. 34 - 40
[4]European Journal of Medicinal Chemistry,2016,vol. 113,p. 11 - 27
[5]European Journal of Medicinal Chemistry,2018,vol. 156,p. 774 - 789

11
[ 4922-98-9 ]
[ 127099-85-8 ]
[ 28610-05-1 ]

Reference： [1]Heterocycles,2007,vol. 71,p. 429 - 436
[2]Tetrahedron Letters,2008,vol. 49,p. 7180 - 7183

12
[ 3679-92-3 ]
[ 4922-98-9 ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 25 - 100℃; for 0.2h;Microwave irradiation; Inert atmosphere;	General procedure: A stirred suspension of the appropriate aryl/heteroaryl aminoguanidine 7a-t (1 mmol) in water (5 mL) was placed in a 10 mL closed vial.The vessel was introduced into the microwave cavity (Pmax=250 psi)using a CEM Discover microwave apparatus. Starting microwave irradiation of 100W was used, the temperature being ramped from 25 to100 °C in 2 min, with rapid stirring and venting. Once 100 °C was reached, the reaction mixture was held at this temperature for 10 min(Power: 100 W). After cooling, the precipitated product was filtered,washed with cold water and dried over P2O5, to furnish the appropriate 3-aryl-/heteroaryl-5-amino-1H-1,2,4-triazole derivatives 8a-t. For the characterization of compound 8a-h, 8k and 8o, see reference [41]. Inaddition, compounds 8i [30] and 8j [42] have shown to possess spectroscopic and analytical data as previously reported. 5.1.3.1. 3-(3-Tolyl)-1H-1,2,4-triazol-5-amine (8l). Synthesized according to method B, compound 8l was obtained as a white solid(yield 63percent); mp 167?168 °C. 1H NMR (d6-DMSO) delta: 2.33 (s, 3H), 6.03(bs, 2H), 7.12 (d, J=7.0 Hz, 1H), 7.23 (t, J=7.0 Hz, 1H), 7.65 (m,2H), 12.0 (bs, 1H). 13C NMR (d6-DMSO) delta: 20.97, 122.39, 125.83,128.14, 128.63, 132.18, 137.22, 157.10, 158.33. MS (ESI): [M+1]+=175.29.

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 2124 - 2128
[2]Heterocycles,2007,vol. 71,p. 429 - 436
[3]Tetrahedron,2007,vol. 63,p. 12888 - 12895
[4]European Journal of Medicinal Chemistry,2013,vol. 67,p. 325 - 334
[5]Bioorganic Chemistry,2018,vol. 80,p. 361 - 374

13
[ 4922-98-9 ]
N-perchloroethenylbenzimidoyl chloride [ No CAS ]
C₁₇H₁₂Cl₃N₅ [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2007,vol. 77,p. 474 - 481

14
[ 4922-98-9 ]
4-methyl-<i>N</i>-(1,2,2-trichloro-vinyl)-benzimidoyl chloride [ No CAS ]
C₁₈H₁₄Cl₃N₅ [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2007,vol. 77,p. 474 - 481

15
[ 4922-98-9 ]
1H-benzotriazole-1-carboxamidine hydrochloride [ No CAS ]
5-amino-1-guanyl-3-phenyl-1,2,4-triazole hydrochloride [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 12888 - 12895

16
[ 4922-98-9 ]
C₁₇H₁₁Cl₂N₅ [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2007,vol. 77,p. 474 - 481

17
[ 4922-98-9 ]
C₁₈H₁₃Cl₂N₅ [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2007,vol. 77,p. 474 - 481

18
[ 613-94-5 ]
[ 4922-98-9 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3019 - 3029
[2]European Journal of Medicinal Chemistry,2013,vol. 67,p. 325 - 334
[3]European Journal of Medicinal Chemistry,2016,vol. 113,p. 11 - 27
[4]European Journal of Medicinal Chemistry,2018,vol. 156,p. 774 - 789

19
[ 4922-98-9 ]
5-Amino-3-[4-(ethoxalylamino)phenyl]-1-[methylamino(thiocarbonyl)]-1H-1,2,4-triazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3019 - 3029

20
[ 4922-98-9 ]
[ 106087-53-0 ]

Reference： [1]Pharmaceutical Chemistry Journal,1986,vol. 20,p. 113 - 117
Khimiko-Farmatsevticheskii Zhurnal,1986,vol. 20,p. 178 - 182

21
[ 4922-98-9 ]
[ 66045-40-7 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 927 - 937

22
[ 4922-98-9 ]
[ 74258-67-6 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 927 - 937

23
[ 4922-98-9 ]
[ 74258-05-2 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 927 - 937

24
[ 4922-98-9 ]
[ 74258-10-9 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 927 - 937

25
[ 4922-98-9 ]
[ 74258-08-5 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 927 - 937

26
[ 4922-98-9 ]
[ 74258-21-2 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 927 - 937

27
[ 4922-98-9 ]
[ 74258-35-8 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 927 - 937

28
[ 4922-98-9 ]
[ 99777-48-7 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 576 - 582
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 682 - 688
[2]Chemistry of Heterocyclic Compounds,2015,vol. 51,p. 1057 - 1060
Khim. Geterotsikl. Soedin.,2015,vol. 51,p. 1057 - 1060,4

29
[ 4922-98-9 ]
[ 99777-42-1 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 576 - 582
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 682 - 688

30
[ 1011-12-7 ]
[ 4922-98-9 ]
[ 1079358-56-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 1419 - 1427

31
[ 638-07-3 ]
[ 4922-98-9 ]
[ 1227417-79-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With acetic acid; at 80℃; for 24h;	Example 1; Part A; To the solution of 3-phenyl-1H-1 ,2,4-triazol-5-amine (0.8 g, 5 mmol) in acetic acid (6 mL) was added ethyl 4-chloro-3-oxobutanoate (0.75 mL, 5.5 mmol). The reaction mixture was stirred for 24 hours at 80 0C, and then cooled to room temperature. The reaction mixture was filtered. The precipitates were washed with ACN and dried to give compound 1-1 in a white powder (872 mg, 67percent yield). 1H NMR (400 MHz, CD3OD) delta 8.24-8.18 (m, 2H), 7.54-7.46 (m, 3H), 6.21 (s, 1H), 4.65 (s, 2H).; Example 6; Part A; To the solution of 3-phenyl-1 H-1 ,2,4-triazol-5-amine (0.8 g, 5 mmol) in acetic acid (6 ml_) was added ethyl 4-chloro-3-oxobutanoate (0.75 ml_, 5.5 mmol).The reaction mixture was stirred for 24 hours at 80 0C, and then cooled to room temperature. The reaction mixture was filtered. The precipitates were washed with ACN and dried to give compound 1-1 in a white powder (872 mg,67percent yield). 1H NMR (400 MHz, CD3OD) delta 8.24-8.18 (m, 2H), 7.54-7.46 (m,3H), 6.21 (s, 1 H), 4.65 (s, 2H).; Example 12; Part A; To the solution of 3-phenyl-1 H-1 ,2,4-triazol-5-amine (0.8 g, 5 mmol) in acetic acid (6 mL) was added ethyl 4-chloro-3-oxobutanoate (0.75 mL, 5.5 mmol). The reaction mixture was stirred for 24 hours at 80 0C, and then cooled to room temperature. The reaction mixture was filtered. The precipitates were washed with ACN and dried to give compound 1-1 in a white powder (872 mg, 67percent yield). 1H NMR (400 MHz, CD3OD) delta 8.24-8.18 (m, 2H), 7.54-7.46 (m, 3H), 6.21 (s, 1 H), 4.65 (s, 2H).
65.1%	With acetic acid; at 80℃;	<strong>[4922-98-9]3-phenyl-1H-1,2,4-triazole-5-amine</strong> (0.95 g, 5.93 mmol) obtained in Step 3-2 was dissolved in 15 mL of acetic acid and ethyl 4-chloroacetoacetate (1.07 g , 6.52 mmol), and the mixture was stirred at 80 ° C. overnight. After completion of the reaction, the precipitate was suction filtered to obtain 5-methylchloro-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one (1.0 g, 86 mmol; yield 65.1percent)

Reference： [1]Patent: WO2010/56631,2010,A1 .Location in patent: Page/Page column 84; 105; 112
[2]Patent: JP6099045,2017,B2 .Location in patent: Paragraph 0065

32
[ 4922-98-9 ]
[ 762-42-5 ]
[ 1227417-80-2 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 20℃;	Example 11; Part A; A reaction mixture of 3-phenyl-1 H-1 ,2,4-tpiazol-5-amiotane (160 mg, 1 mmol) and dimethyl but-2-ynediotaoate (123 mul_, 1 mmol) in methanol (2 ml_) was stirred at room temperature for overnight Purification using reverse phase HPLC gave compound 11-1 as a solid after lyophilization HPLC-MS RT= 3 08 mm, mass calculated for formula Ci3H10N4O3270 08, observed LCMS m/z 271 28 (M+H)

Reference： [1]Patent: WO2010/56631,2010,A1 .Location in patent: Page/Page column 111

33
[ 2063-17-4 ]
[ 4922-98-9 ]
[ 1227418-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	In ISOPROPYLAMIDE; at 180℃; for 0.333333h;Microwave irradiation;	Example 38; STEP A; To the solution of 3-phenyl-1H-1 ,2,4-triazol-5-amine (32 mg, 0.2 mmol) in DMA (0.5 ml_) was added ethyl 4-chloro-4,4-difluoro-3-oxobutanoate (40 mg, 0.2 mmol). The reaction mixture was stirred in microwave at 180 0C for 20 minutes, and then cooled to room temperature. The product, compound 38-1 , was purified by reverse phase HPLC.

Reference： [1]Patent: WO2010/56631,2010,A1 .Location in patent: Page/Page column 139

34
[ 1225855-93-5 ]
[ 4922-98-9 ]
[ 1227415-58-8 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; at 160℃; for 0.333333h;Microwave irradiation;	Part C; A reaction mixture of compound 14-2 (50 mg, 0.2 mmol) and 3-phenyl-1 H- 1 ,2,4-triazol-5-amine (32 mg, 0.2 mmol) in AcOH (1 mL) was stirred at 160 0C for 20 minutes in microwave. Purification using reverse phase HPLC gave compound 14-3 after lyophilization.

Reference： [1]Patent: WO2010/56631,2010,A1 .Location in patent: Page/Page column 115

35
[ 1227417-82-4 ]
[ 4922-98-9 ]
[ 1227415-59-9 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; at 160℃; for 0.333333h;Microwave irradiation;	Part C; A reaction mixture of compound 15-2 (79 mg, 0.3 mmol) and 3-phenyl-1 H- 1 ,2,4-triazol-5-amine (48 mg, 0.3 mmol) in AcOH (1 mL) was stirred at 160 0C for 20 minutes in microwave. Purification using reverse phase HPLC gave compound 15-3 after lyophilization.

Reference： [1]Patent: WO2010/56631,2010,A1 .Location in patent: Page/Page column 116

36
[ 1227417-93-7 ]
[ 4922-98-9 ]
[ 1227416-03-6 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 80℃;	STEP E; A reaction mixture of compound 35-4 (28.3 mg, 0.1 mmol) and 3-phenyl-1H- 1 ,2,4-triazol-5-amine (16 mg, 0.1 mmol) in ethanol was stirred at 80 0C for overnight. The product was purified using reverse phase HPLC.

Reference： [1]Patent: WO2010/56631,2010,A1 .Location in patent: Page/Page column 136

37
[ 1227417-97-1 ]
[ 4922-98-9 ]
[ 1227416-05-8 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 80℃;	STEP E; A reaction mixture of compound 37-4 (28.4 mg, 0.1 mmol) and 3-phenyl-1 H- 1 ,2,4-tpiazol-5-amine (16 mg, 0.1 mmol) in ethanol was stirred at 80 0C for overnight. The product was purified using reverse phase HPLC. The two pure enantiomers (37-6 and 37-7) were chirally separated from 37-5 by chiral cell column (20 micron, 50 X 500 mm, 100percent MeOH with 0.1percent TFA as mobile phase at 80 mL/min).

Reference： [1]Patent: WO2010/56631,2010,A1 .Location in patent: Page/Page column 138-139

38
[ 874-42-0 ]
[ 105-45-3 ]
[ 4922-98-9 ]
[ 512838-68-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4395 - 4398

39
[ 2009-81-6 ]
[ 4922-98-9 ]
[ 1253696-37-5 ]

Reference： [1]Synthesis,2010,p. 2767 - 2770

40
[ 4922-98-9 ]
[ 10495-62-2 ]

Reference： [1]Russian Journal of Applied Chemistry,2011,vol. 84,p. 1890 - 1896

41
[ 4922-98-9 ]
[ 1410904-72-1 ]

Reference： [1]Heterocycles,2012,vol. 85,p. 2515 - 2522

42
[ 4922-98-9 ]
[ 545-06-2 ]
[ 1410904-63-0 ]

Reference： [1]Heterocycles,2012,vol. 85,p. 2515 - 2522

43
[ 4922-98-9 ]
[ 28610-03-9 ]

Reference： [1]Heterocycles,2013,vol. 87,p. 147 - 154

44
[ 4637-24-5 ]
[ 4922-98-9 ]
[ 1428770-64-2 ]

Reference： [1]Heterocycles,2013,vol. 87,p. 147 - 154

45
[ 4922-98-9 ]
[ 1447727-54-9 ]

Reference： [1]Patent: US2013/184248,2013,A1
[2]Patent: WO2013/107761,2013,A1

46
[ 4922-98-9 ]
[ 1447726-61-5 ]

Reference： [1]Patent: US2013/184248,2013,A1

47
[ 4922-98-9 ]
[ 15777-59-0 ]

Yield	Reaction Conditions	Operation in experiment
11 g	With hydrogen bromide; sodium nitrite; at -5 - 20℃; for 0.333333h;Reflux;	6.02.04.37 5-bromo-3-phenyl-lH-(l, 2, 4) triazole 115 mL bromine hydro acid was added to 9.5 g 5-phenyl-2H-(l, 2, 4) triazol-3-ylamine and 12.3 g sodiumnitrite at -5°C. The reaction was warmed to RT and refluxed for 20 min. Then the mixture was cooled and basicfied with sodiumdicarbonate and extracted with ethyl acetate. The organic layer was dried and evaporated to give 11 g of the desired product. Rt: 1.07 min (method B), (M+H)+: 223/225
11 g	With hydrogen bromide; sodium nitrite; at -5 - 20℃; for 0.333333h;Reflux;	6.02.04.37 5-bromo-3-phenyl-1H-(1,2,4)triazole 115 mL bromine hydro acid was added to 9.5 g <strong>[4922-98-9]5-phenyl-2H-(1,2,4)triazol-3-ylamine</strong> and 12.3 g sodiumnitrite at -5° C. The reaction was warmed to RT and refluxed for 20 min. Then the mixture was cooled and basicfied with sodiumdicarbonate and extracted with ethyl acetate. The organic layer was dried and evaporated to give 11 g of the desired product. Rt: 1.07 min (method B), (M+H)+: 223/225 By using the same synthesis strategy as for 5-bromo-3-phenyl-1H-(1,2,4)triazole the following compound was obtained:

Reference： [1]Patent: WO2013/107761,2013,A1 .Location in patent: Page/Page column 71
[2]Patent: US2013/184248,2013,A1 .Location in patent: Paragraph 0346; 0347; 0348

48
[ 420-04-2 ]
[ 4922-98-9 ]
[ 122-51-0 ]
[ 28610-03-9 ]

Reference： [1]RSC Advances,2013,vol. 3,p. 15850 - 15855

49
[ 4922-98-9 ]
[ 16182-04-0 ]
[ 40597-94-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	In N,N-dimethyl-formamide; at 20℃; for 5h;	Synthesis of N-carbethoxy-N'-(3-phenyl-1H-1,2,4-triazol-5-yl)thiourea (17). To the solution of<strong>[4922-98-9]3-phenyl-1,2,4-triazol-5-amine</strong> (12, 0.48 g, 3 mmol) in anhydrous DMF (4 mL), ethoxycarbonylisothiocyanate (0.43 mL, 3.3 mmol) was added. After stirring the mixture for 5 h at room temperature,cold water (60 mL) was added. The precipitated product was filtered, washed with cold water andrecrystalized from EtOH. Yield 0.74 g, 85%; mp 180-181 C (EtOH). 1H-NMR (300 MHz, DMSO-d6): 1.28 (3H, t, J = 7.1 Hz, CH3), 4.25 (2H, q, J = 7.1 Hz, CH2), 7.37-7.66 (3H, m, H-30, H-40 and H-50), 8.01(2H, d, J = 7.2 Hz, H-20 and H-60), 11.56* (12H, brs, 2NH), 11.87 (1H, brs, NH), 12.16 (1H, brs, NH), 13.93(1H, brs, N(1)H), 14.47 (1H, brs, N(1)H). -signals of the minor tautomer. Combustion elementalanalysis calculated for C12H13N5O2S: C, 49.47; H, 4.50; N, 24.04. Found: C, 49.33; H, 4.62; N, 23.95.
	In N,N-dimethyl-formamide; at 20℃; for 5h;	General procedure: Initially, amidoguanidines (7) were prepared via the reaction of substituted benzoyl chloride (5) (10 mmol) and aminoguanidine hydrochloride (6) (20 mmol). The obtained intermediates (7) were then treated with microwave irradiation power (100 W) for 8-15 min in water to generate 5-amino-1,2,4-triazoles (8) [18] . Subsequently, 5-amino-1,2,4-triazoles (8) (3 mmol) were reacted with ethoxycarbonyl isothiocyanate (3.3 mmol) in anhydrous DMF (4 ml) at room temperature, leading to formation of thiourea derivatives (9).

Reference： [1]Molecules,2019,vol. 24
[2]Chemical Biology and Drug Design,2013,vol. 82,p. 351 - 360
[3]Bioorganic Chemistry,2013,vol. 50,p. 34 - 40
[4]Medicinal Chemistry Research,2013,vol. 22,p. 6010 - 6021

50
[ 4922-98-9 ]
[ 16182-04-0 ]
[ 19923-10-5 ]

Yield	Reaction Conditions	Operation in experiment
37%	In acetone; for 0.25h;Cooling with ice;	Synthesis of 5-amino-1-carbethoxythiocarbamoyl-1,2,4-triazole (16). To a solution of acetone(30 mL), <strong>[4922-98-9]3-phenyl-1,2,4-triazol-5-amine</strong> (12, 3.20 g, 20 mmol) and ethoxycarbonyl isothiocyanate(2.62 mL, 20 mmol) were added. The reaction mixture was stirred on an ice-bath for 15 min. The yellowprecipitate formed was filtered immediately. Yield 2.16 g, 37%; mp 207-209 C. 1H-NMR (300 MHz,DMSO-d6): 2.63 (3H, s, SMe), 7.47-7.57 (3H, m, H-30, H-40 and H-50), 8.03 (2H, dd, J = 6.8, 3.0 Hz,H-20 and H-60), 8.64 (2H, s, NH2). 13C-NMR (75 MHz, DMSO-d6): 18.8, 126.6 (2C), 128.8 (2C), 129.1,130.6, 157.5, 158.8, 199.5. Combustion elemental analysis calculated for C12H13N5O2S: C, 49.47; H, 4.50;N, 24.04. Found: C, 49.20; H, 4.67; N, 23.88.

Reference： [1]Molecules,2019,vol. 24
[2]Chemical Biology and Drug Design,2013,vol. 82,p. 351 - 360

51
[ 4922-98-9 ]
[ 1431968-81-8 ]

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 67,p. 325 - 334
[2]Chemical Biology and Drug Design,2013,vol. 82,p. 351 - 360
[3]Medicinal Chemistry Research,2013,vol. 22,p. 6010 - 6021

52
[ 4922-98-9 ]
[ 40597-80-6 ]

Reference： [1]Chemical Biology and Drug Design,2013,vol. 82,p. 351 - 360

53
[ 4922-98-9 ]
[ 20085-45-4 ]

Reference： [1]Chemical Biology and Drug Design,2013,vol. 82,p. 351 - 360
[2]European Journal of Medicinal Chemistry,2013,vol. 67,p. 325 - 334
[3]Bioorganic Chemistry,2013,vol. 50,p. 34 - 40
[4]Medicinal Chemistry Research,2013,vol. 22,p. 6010 - 6021

54
[ 4922-98-9 ]
[ 68-12-2 ]
ethyl isocyano formate [ No CAS ]
[ 1431968-94-3 ]

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 67,p. 325 - 334

55
ethoxycarbonyl isothiocyanate [ No CAS ]
[ 4922-98-9 ]
[ 40597-94-2 ]

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 67,p. 325 - 334

56
[ 98-88-4 ]
[ 4922-98-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 67,p. 325 - 334
[2]Patent: JP6099045,2017,B2
[3]Bioorganic Chemistry,2018,vol. 80,p. 361 - 374

57
[ 4922-98-9 ]
[ 40597-86-2 ]

Reference： [1]Chemical Biology and Drug Design,2013,vol. 82,p. 351 - 360
[2]Molecules,2019,vol. 24

58
[ 4922-98-9 ]
[ 40597-88-4 ]

Reference： [1]Bioorganic Chemistry,2013,vol. 50,p. 34 - 40
[2]Medicinal Chemistry Research,2013,vol. 22,p. 6010 - 6021

59
[ 4922-98-9 ]
2-phenyl-5-(ethylthio)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-one [ No CAS ]

Reference： [1]Bioorganic Chemistry,2013,vol. 50,p. 34 - 40

60
[ 4922-98-9 ]
2-phenyl-5-(propylthio)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-one [ No CAS ]

Reference： [1]Bioorganic Chemistry,2013,vol. 50,p. 34 - 40

61
[ 4922-98-9 ]
2-phenyl-5-(benzylthio)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-one [ No CAS ]

Reference： [1]Bioorganic Chemistry,2013,vol. 50,p. 34 - 40

62
[ 4922-98-9 ]
ethyl isocyano formate [ No CAS ]
[ 1431968-94-3 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 6010 - 6021

63
[ 1028843-08-4 ]
[ 4922-98-9 ]
[ 1029520-91-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 72 - 76

64
[ 100-52-7 ]
[ 126-81-8 ]
[ 4922-98-9 ]
6,6-dimethyl-2,9-diphenyl-5,6,7,9-tetrahydro-[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2014,vol. 50,p. 1485 - 1495
Zhurnal Organicheskoi Khimii,2014,vol. 50,p. 1498 - 1508,11

65
[ 100-52-7 ]
[ 126-81-8 ]
[ 4922-98-9 ]
6,6-dimethyl-2,9-diphenyl-6,7-dihydro[1,2,4]tri-azolo[5,1-b]quinazolin-8(5H)-one [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2014,vol. 50,p. 1485 - 1495
Zhurnal Organicheskoi Khimii,2014,vol. 50,p. 1498 - 1508,11

66
[ 4922-98-9 ]
[ 87-13-8 ]
[ 489412-14-8 ]

Yield	Reaction Conditions	Operation in experiment
67%	With acetic acid; at 120℃; for 3h;	General procedure: A solution of aminotriazole 11a?m (3.1mmol), glacial acetic acid (5mL), and diethyl ethoxymethylenemalonate (4.6mmol) was refluxed for 3h. After cooling to room temperature, the resulting precipitate was collected by filtration, washed with cold water and dried. The residue was stirred with cold ethyl ether (20mL) and filtered to afford the desired product. Following general procedure C, compound 12c was isolated as a white solid. Yield 67percent, mp>300°C. 1H NMR (200MHz, DMSO-d6) delta: 14.00 (br s, 1H); 8.64 (s, 1H); 8.14?8.10 (m, 2H); 7.55 (m, 3H); 4.26 (q, J=7.0Hz, 2H); 1.28 (t, J=6.8Hz, 3H)

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 113,p. 11 - 27

67
[ 4922-98-9 ]
[ 1421702-96-6 ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 113,p. 11 - 27

68
[ 4922-98-9 ]
[ 1421702-67-1 ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 113,p. 11 - 27

69
[ 4922-98-9 ]
4,7-dihydro-N-(3,5-dimethyladamantan-1-yl)-7-oxo-4-pentyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 113,p. 11 - 27

70
[ 4922-98-9 ]
N-cyclohexyl-4,7-dihydro-7-oxo-4-pentyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 113,p. 11 - 27

71
[ 4922-98-9 ]
N-cycloheptyl-4,7-dihydro-7-oxo-4-pentyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 113,p. 11 - 27

72
[ 4922-98-9 ]
ethyl nitrocyanoacetate potassium salt [ No CAS ]
C₁₀H₆N₇O₂^(1-)*K⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Solution A. A solution of KOH (0.56 g, 0.01 mol) and potassium salt of ethyl nitrocyanoacetate (1.96 g, 0.01 mol) in2 (8 ml) was stirred at room temperature for 3 h, then kept overnight. 4 M aqueous KOAc (8 ml, 0.03 mol) was added to the resulting solution, and the mixture cooled to 5°. A mixture of 3-aminoazole 1a?i (0.010 mol), EtOH (10 ml),H2O (10 ml), and concentrated HCl (2.5 ml, 0.030 mol)was treated with a solution of NaNO2 (0.759 g, 0.011 mol)in H2O (3 ml) at ?5 °. The reaction mixture was kept at this temperature for 10 min, then added to the solution A. The mixture was kept at room temperature for 1 h; the formed precipitate was filtered, stirred with 40percent aqueous H2SO4 (10 ml) (AcOH (10 ml) was used for compound 4e), filtered, and dried. The obtained hydrazone 3a?i was heated under reflux in DMF for 3 h. The solvent was evaporated, the residue triturated in water, filtered, and dried.

Reference： [1]Chemistry of Heterocyclic Compounds,2015,vol. 51,p. 1057 - 1060
Khim. Geterotsikl. Soedin.,2015,vol. 51,p. 1057 - 1060,4

73
[ 4922-98-9 ]
C₁₀H₇N₇O₂ [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2015,vol. 51,p. 1057 - 1060
Khim. Geterotsikl. Soedin.,2015,vol. 51,p. 1057 - 1060,4

74
[ 4922-98-9 ]
5-{(3-bromophenoxy)methyl}-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one [ No CAS ]