[ CAS No. 648430-85-7 ] {[proInfo.proName]}

Name: 648430-85-7|Ethyl 3-benzyl-1H-1,2,4-triazole-5-carboxylate|97%
Brand: Ambeed
SKU: A207119
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Quality Control of [ 648430-85-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 648430-85-7 ]

SDS Specification

Alternatived Products of [ 648430-85-7 ]

Product Details of [ 648430-85-7 ]

CAS No. :	648430-85-7	MDL No. :	MFCD19482176
Formula :	C₁₂H₁₃N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZDYNKUMTNKZJGQ-UHFFFAOYSA-N
M.W :	231.25	Pubchem ID :	59531741
Synonyms :

Calculated chemistry of [ 648430-85-7 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.25
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	61.92
TPSA :	67.87 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.78
Log Po/w (XLOGP3) :	2.5
Log Po/w (WLOGP) :	1.57
Log Po/w (MLOGP) :	1.18
Log Po/w (SILICOS-IT) :	2.56
Consensus Log Po/w :	1.92

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.0
Solubility :	0.233 mg/ml ; 0.00101 mol/l
Class :	Soluble
Log S (Ali) :	-3.57
Solubility :	0.0621 mg/ml ; 0.000269 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.27
Solubility :	0.0123 mg/ml ; 0.0000533 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.4

Safety of [ 648430-85-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 648430-85-7 ]

* 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 [ 648430-85-7 ]

[ 648430-85-7 ] Synthesis Path-Downstream 1~29

1
C₁₂H₁₄N₂O₃ [ No CAS ]
[ 648430-85-7 ]

Yield	Reaction Conditions	Operation in experiment
49%	at 200℃; for 0.25h; Neat (no solvent);	I-1.2 Step 2: Ethyl 5-Benzyl-1H-1 ,2,4-triazole-3-carboxylate (i-3); Adapting a procedure similar to that described in Catarzi, D.; et al J. Med. Chem.; 38; 1995; 2196-2201, neat methyl 2-amino[(phenylacetyl)hydrazono]acetate {i-2, 6.5 g, 26.1 mmol) in a flask was placed in a pre-heated oil bath at 200cC for 15 minutes. The melt was allowed to cool, the resultant solid taken up into MeOH {30 mL), and then the solvent was evaporated. The resultant white solid was suspended in ether (60 mL), stirred for 10 minutes, filtered off, washed with ether, and dried under vacuum to give the title compound i-3 (3.1 mg, yield 49%), which was used without further purification. 1H NMR (300 MHz, DMSO-d6) 1.30 (t, J=7.2 Hz, 3 H) 4.14 (s, 2 H) 4.31 (q, J=7.2 Hz, 2 H) 7.23 - 7.38 (m, 5 H) 14.50 (s, 1 H). LCMS (M+H)+: 232

Reference： [1]Current Patent Assignee: PFIZER INC - WO2008/17932, 2008, A2 Location in patent: Page/Page column 52-53

2
[ 40741-46-6 ]
[ 648430-85-7 ]
ethyl 1-[5-(aminosulfonyl)pyridin-2-yl]-5-benzyl-1H-1,2,4-triazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With potassium tert-butylate; at 120℃; for 3h;Microwave irradiation;	Step 3: Ethyl 1-[5-(Aminosulfonyl)pyridin-2-yl]-5-benzyl-1H-1,2,4-triazole-3-carboxylate (i-4); To the mixture of ethyl 5-benzyl-1H-1,2,4-t?'azole-3-carboxyIate (i-3, 1.16 g, 5.00 mmol) and 6- chloropyridine-3-sulfonamide (1.73 g, 9.00 mmol, Adams; J. Am. Chem. Soc. 71 , 1949, 387 -389) in DMSO (10 ml_) was added potassium t-butoxide (842 mg, 7.50 mmol) . The mixture was heated in a microwave apparatus at 12O0C for 90 minutes. TLC showed some of the starting material left. The solution was heated at 12O0C in microwave for another 90 minutes, cooled. The mixture was diluted with water (200 mL) and 1N HCI (5 mL), decanted. The sticky residue was suspended into MeOH (5 mL), then diluted with water (200 mL), the mixture was stirred rapidly for half hour, filtered. The yellow solid was washed with water and dried under vacuum to give the title compound i-4 (860 mg, yield 44%), which was used without further purification. Regiochemistry assumed from a similar experiment described for pyrazole Example mm-1. NMR provided in table. Elemental Analysis: Calcd for C17H17N5O4S: C, 52.70; H, 4.42; N, 18.08. Found: C, 52.57; H, 4.45; N, 18.00.

Reference： [1]Patent: WO2008/17932,2008,A2 .Location in patent: Page/Page column 53

3
[ 648430-85-7 ]
[ 1622848-92-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium hydroxide / tetrahydrofuran; water / 20 h / 20 °C 1.2: pH Ca_. 2 2.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 0.17 h 2.2: 0.17 h / 20 °C
	Multi-step reaction with 2 steps 1.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C 1.2: pH Ca_.2 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 15 °C 2.2: 1 h / 15 - 20 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/125444, 2014, A1
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2018/7973, 2018, A2

4
[ 648430-85-7 ]
[ 1622849-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium hydroxide; water / methanol / 3 h / 20 - 25 °C 2: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / dichloromethane; ethyl acetate / 1.13 h / 20 °C / Cooling with ice
	Multi-step reaction with 2 steps 1: lithium hydroxide; water / 3 h / 20 - 25 °C 2: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / dichloromethane; ethyl acetate / 1.13 h / 20 °C / Cooling with ice

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2018/154520, 2018, A1
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2020/44206, 2020, A1

5
[ 937-39-3 ]
[ 648430-85-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ethanol / 12 h / 0 - 25 °C 2: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / 170 °C
	Multi-step reaction with 2 steps 1: ethanol / 24 h 2: diphenylether / 8 h / 170 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: triethylamine / ethanol / 12 h / 20 °C 2: diphenylether / 0.02 h / Reflux

Multi-step reaction with 2 steps 1: ethanol / 20 °C 2: diphenylether / 4 h / 200 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM - WO2021/46515, 2021, A1
[2]Current Patent Assignee: SECOND MILITARY MEDICAL UNIVERSITY - CN112778291, 2021, A
[3]Khomenko, Dmytro M.; Doroshchuk, Roman O.; Ohorodnik, Yulia M.; Ivanova, Hanna V.; Zakharchenko, Borys V.; Raspertova, Ilona V.; Vaschenko, Oleksandr V.; Dobrydnev, Alexey V.; Grygorenko, Oleksandr O.; Lampeka, Rostyslav D. [Chemistry of Heterocyclic Compounds, 2022, vol. 58, # 2-3, p. 116 - 128][Khim. Geterotsikl. Soedin., 2022, vol. 58, # 2-3, p. 116 - 128]
[4]Fu, Peng; Hao, Yanan; Li, Jiao; Qu, Zhuo; Shao, Hongming; Shi, Ying; Yu, Jianqiang; Zhang, Wannian; Zhuang, Chunlin [European Journal of Medicinal Chemistry, 2022, vol. 236]

6
ethyl 2-imino-2-(2-(2-phenylacetyl)hydrazineyl)acetate [ No CAS ]
[ 648430-85-7 ]

Yield	Reaction Conditions	Operation in experiment
	In 5,5-dimethyl-1,3-cyclohexadiene at 170℃; for 6h;	9 Ethyl 5-benzyl-1H-1,2,4-triazole-3-carboxylate A mixture the product from the previous step (2 g, 8.02 mmol, 1 eq) in xylene (30 mL) was stirred at 170 °C for 6 hr. The reaction mixture was concentrated to afford the title compound (1.8 g, crude) as a light yellow solid. MS (ES+) C12H13N3O2 requires: 231, found: 232 [M+H]+.

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM - WO2021/46515, 2021, A1 Location in patent: Paragraph 0556

7
[ 648430-85-7 ]
lithium 5-benzyl-1H-1,2,4-triazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
130 mg	With lithium hydroxide In methanol; water at 0 - 50℃; for 14h;	9 Lithium 5-benzyl-1H-1,2,4-triazole-3-carboxylate To a solution of ethyl 5-benzyl-1H-1,2,4-triazole-3-carboxylate (150 mg, 648.65 umol, 1 eq) in MeOH (1.5 mL) was added LiOH (32 mg, 1.34 mmol, 2.06 eq) in H2O (1.5 mL) at 0 °C. The mixture was stirred at 50 °C for 14 hr. The reaction mixture was concentrated under reduced pressure to afford the title compound (130 mg, 621.62 umol, 96% yield) as a light yellow solid. MS (ES-) C10H8LiN3O2 requires: 203, found: 202 [M-Li]-.

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM - WO2021/46515, 2021, A1 Location in patent: Paragraph 0557

8
[ 648430-85-7 ]
5-benzyl-N-(3-chloro-2-fluorophenyl)-1H-1,2,4-triazole-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium hydroxide / methanol; water / 14 h / 0 - 50 °C 2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 14 h / 0 - 25 °C

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM - WO2021/46515, 2021, A1

9
[ 648430-85-7 ]
5-benzyl-N-(3-chloro-2-fluorophenyl)-1-methyl-1,2,4-triazole-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / methanol; water / 14 h / 0 - 50 °C 2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 14 h / 0 - 25 °C 3: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM - WO2021/46515, 2021, A1

10
(E)-2-amino-2-(2-(2-(phenyl)acetyl)hydrazono)acetate ethyl ester [ No CAS ]
[ 648430-85-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	In diphenylether at 170℃; for 8h; Inert atmosphere;	1.g Step g: 5-benzyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester Add (E)-2-amino-2-(2-(2-(phenylphenylacetyl)hydrazino)ethyl acetate (2.70g, 10.90mmol) to diphenyl ether (30mL),Heat for 8 hours at 170°C under nitrogen protection. TLC monitoring, after the completion of the reaction, the reaction solution was cooled to room temperature, and a solid precipitated out. Add petroleum ether, stir the reaction solution in an ice/water bath for 15 minutes, filter to obtain a solid, wash the solid with water and petroleum ether,Obtain 2.4 g of ethyl 5-benzyl-1H-1,2,4-triazole-3-carboxylate as a white solid compound,The yield was 95%.

Reference： [1]Current Patent Assignee: SECOND MILITARY MEDICAL UNIVERSITY - CN112778291, 2021, A Location in patent: Paragraph 0121; 0124; 0137-0138

11
[ 648430-85-7 ]
(R)-5-benzyl-N-(5-methyl-4-thioxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-1H-1,2,4-triazole-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium hydroxide; water / tetrahydrofuran / 20 h / 15 - 20 °C 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dimethyl sulfoxide / 0.5 h / 0 - 20 °C