4970-53-0

Basic information

• Product Name: 5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: TIMTEC-BB SBB005498;ETHYL 5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLATE;5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER;5-Amino-1,3,4-oxadiazole-2-carboxylic acid ethyl;Ethyl 5-amino-1,3,4-oxadiazole-2-carboxylate 97%;SBB005498;ZINC02576102
• CAS NO: 4970-53-0
• Molecular Formula: C₅H₇N₃O₃
• Molecular Weight: 157.13
• Mol File: 4970-53-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 199 °C
• Boiling Point: 289.1 °C at 760 mmHg
• Flash Point: 128.6 °C
• Appearance: /
• Density: 1.362 g/cm³
• Vapor Pressure: 0.00224mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: 2-8°C
• PKA: -2.59±0.13(Predicted)
• CAS DataBase Reference: 5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER(4970-53-0)
• EPA Substance Registry System: 5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER(4970-53-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4970-53-0(Hazardous Substances Data)

Usage

General Description

5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER is a chemical compound with the molecular formula C6H7N3O3. It is an ethyl ester derivative of oxadiazole-carboxylic acid, which is commonly used in organic synthesis and pharmaceutical research. 5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER is a white to off-white solid that is soluble in polar solvents such as ethanol and dimethyl sulfoxide. It is known for its potential as a building block in the synthesis of various pharmaceutical compounds due to its unique chemical structure and versatile reactivity. Additionally, this compound has been studied for its potential antimicrobial and anticancer activities, making it a promising candidate for further research and development in the pharmaceutical industry.

InChI:InChI=1/C5H7N3O3/c1-2-10-4(9)3-7-8-5(6)11-3/h2H2,1H3,(H2,6,8)

Synthetic route

bromocyane (506-68-3) + oxalic acid diethyl ester (95-92-1) → 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0)

Conditions	Yield
Stage #1: oxalic acid diethyl ester With hydrazine hydrate In ethanol at -20℃; for 0.5h; Stage #2: bromocyane In ethanol; water at 20℃; for 1h;	31%

ethyl 2-(2-carbamoylhydrazono)acetate (999-47-3) → 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid; sodium acetate / 24 h / 20 °C 2: triethylamine / toluene / 0.17 h / 20 - 80 °C View Scheme
Multi-step reaction with 2 steps 1: bromine; sodium acetate; acetic acid / 24 h / 20 °C 2: triethylamine / toluene / 0.17 h / 20 - 80 °C View Scheme
Multi-step reaction with 2 steps 1: sodium acetate; bromine / acetic acid / 24 h / 20 °C 2: triethylamine / toluene / 0.17 h / 80 °C View Scheme

ethyl 2-bromo-2-(2-carbamoylhydrazono)acetate (13599-88-7) → 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0)

Conditions	Yield
With triethylamine In toluene at 20 - 80℃; for 0.166667h;	1.04 g
With triethylamine In toluene at 20 - 80℃; for 0.166667h;	1.04 g
With triethylamine In toluene at 80℃; for 0.166667h;	1.04 g

5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → 5-amino-1,3,4-oxadiazole-2-carboxylic acid amide (4970-55-2)

Conditions	Yield
With ammonia In methanol at 20℃; for 18h; Concentration; Temperature; Solvent; Sealed tube;	99%

(1R,2R)-2-(4-bromobenzoyl)cyclohexane-1-carboxylic acid + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → ethyl 5-({[(1R,2R)-2-(4-bromobenzoyl)cyclohexyl]carbonyl}amino)-1,3,4-oxadiazole-2-carboxylate

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 80℃; for 12h;	98%

5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → sodium 5-amino-1,3,4-oxadiazole-2-carboxylate

Conditions	Yield
With water; sodium hydroxide for 1h;	82%

2,4-dichloro-2-methylpyrimidine (1780-26-3) + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → 5-(6-chloro-2-methylpyrimidin-4-ylamino)-[1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	71%

4-pentynoic acid (6089-09-4) + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → ethyl 5-[(pent-4-ynoyl)amino]-1,3,4-oxadiazole-2-carboxylate

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 18h;	70%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 25℃; for 18h;	70%

4-chloro-2-methyl-6-phenyl-pyrimidine (2915-15-3) + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → 5-(2-methyl-6-phenylpyrimidin-4-ylamino)-[1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	70%

di-tert-butyl dicarbonate (24424-99-5) + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → ethyl 5-[[(tert-butoxy)carbonyl]amino]-1,3,4-oxadiazole-2-carboxylate (1258411-53-8)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃;	67%
Stage #1: 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 16h;	56.2%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;	55%

4-chloro-2-methyl-6-(4-nitro-phenyl)-pyrimidine + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → 5-[2-methyl-6-(4-nitrophenyl)pyrimidin-4-ylamino][1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	66%

4-chloro-2-methyl-6-(3-nitro-phenyl)-pyrimidine + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → 5-[2-methyl-6-(3-nitrophenyl)pyrimidin-4-ylamino][1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	61%

4-chloro-2-methyl-6-(4-methylpiperazin-1-yl)pyrimidine + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → 5-[2-methyl-6-(4-methylpiperazin-1-yl)pyrimidin-4-ylamino][1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	55%
With xantphos; palladium diacetate; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	55%

methyl iodide (74-88-4) + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → ethyl 5-((bis(methylthio)methylene)amino)-1,3,4-oxadiazole-2-carboxylate

Conditions	Yield
Stage #1: 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester With sodium hydroxide In N,N-dimethyl-formamide for 0.166667h; Stage #2: In N,N-dimethyl-formamide for 0.333333h; Stage #3: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;	37%

1-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanone + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → 5-[2-methyl-6-(4-acetylpiperazin-1-yl)pyrimidin-4-ylamino][1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	36%
With xantphos; palladium diacetate; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	36%

2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol (127116-19-2) + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → 5-{6-[4-(2-hydroxy-ethyl)piperazin-1-yl]-2-methylpyrimidin-4-ylamino}-[1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	20%
With xantphos; palladium diacetate; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	20%

4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzoic acid + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → ethyl 5-(4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzamido)-1,3,4-oxadiazole-2-carboxylate

Conditions	Yield
Stage #1: 4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzoic acid; 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With dmap; trimethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;	9%

N,N-dimethylformamide diethyl diacetal (1188-33-6) + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → 5-(dimethylamino-methyleneamino)-[1,3,4]oxadiazole-2-carboxylic acid ethyl ester (37582-75-5)

Conditions	Yield
In ethanol

5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → ethyl 5-bromo-1,3,4-oxadiazole-2-carboxylate (916889-45-7)

Conditions	Yield
Stage #1: 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester With copper(ll) bromide In acetonitrile at 20℃; for 0.25h; Stage #2: With tert.-butylnitrite In acetonitrile at 20 - 50℃; for 2.5h;

ethylmagnesium bromide (925-90-6) + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → 3-(5-amino-1,3,4-oxadiazol-2-yl)pentan-3-ol (910656-41-6)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 0.5h; Mechanism;

cyclopropylmagnesium bromide (23719-80-4) + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → (5-amino-1,3,4-oxadiazol-2-yl)(dicyclopropyl)methanol

Conditions	Yield
Stage #1: cyclopropylmagnesium bromide; 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester In tetrahydrofuran at -78 - 20℃; Stage #2: With ammonium chloride In tetrahydrofuran; water

ethylmagnesium bromide (925-90-6) + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → 1-(5-amino-1,3,4-oxadiazol-2-yl)propan-1-one

Conditions	Yield
Stage #1: ethylmagnesium bromide; 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester In tetrahydrofuran at -78 - 20℃; Stage #2: With ammonium acetate In tetrahydrofuran; water

cinchophen (132-60-5) + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → N-(5-ethoxycarbonyl-1,3,4-oxadiazol-2-yl)-2-phenyl-4-quinolinecarboxamide (1236056-69-1)

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide

2-phenylquinoline-4-carbonyl chloride (59661-86-8) + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → N-(5-ethoxycarbonyl-1,3,4-oxadiazol-2-yl)-2-phenyl-4-quinolinecarboxamide (1236056-69-1)

Conditions	Yield
With pyridine at 20 - 60℃;

5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → Ethyl 5-({[(3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-pyrazolidinyl]carbonyl}amino)-1,3,4-oxadiazole-2-carboxylate (1398750-50-9)

5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → 1,3,4-oxadiazol-2-amine (3775-60-8)

Conditions	Yield
With sodium hydroxide In water for 0.0833333h;	0.02 g
With water; sodium hydroxide at 20℃; for 0.0833333h;	0.02 g
With sodium hydroxide In water at 20℃; for 0.0833333h;	0.02 g

6-(5-chloro-7-methoxy-2,3-diphenylpyrazolo[1,5-a] pyrimidin-6-yl)quinoline + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → ethyl 5-((7-oxo-2,3-diphenyl-6-(quinolin-6-yl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-5-yl)amino)-1,3,4-oxadiazole-2-carboxylate

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;

5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → ethyl 5-((6-chloro-1H-benzo[d]imidazol-2-yl)amino)-1,3,4-oxadiazole-2-carboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / N,N-dimethyl-formamide / 0.17 h 1.2: 0.33 h 1.3: 0.5 h / 0 - 20 °C 2.1: N,N-dimethyl-formamide / 16 h / 120 °C View Scheme

4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzoic acid + 5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → ethyl 5-(4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzamido)-1,3,4-oxadiazole-2-carboxylate + ethyl 5-(4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzamido)-1,3,4-oxadiazole-2-carboxylate

Conditions

Yield

Stage #1: 4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzoic acid; 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; Sealed tube; Stage #2: With dmap; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Sealed tube; Overall yield = 9%; Overall yield = 19 mg;

A n/a B n/a

Upstream product

• 999-47-3 ethyl 2-(2-carbamoylhydrazono)acetate 
• 13599-88-7 ethyl 2-bromo-2-(2-carbamoylhydrazono)acetate 
• 506-68-3 bromocyane 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 916889-45-7 ethyl 5-bromo-1,3,4-oxadiazole-2-carboxylate 
• 3775-60-8 1,3,4-oxadiazol-2-amine 

Relevant articles and documents

HETEROCYCLIC AMIDE COMPOUND

PROBLEM TO BE SOLVED: To provide a heterocyclic amide compound useful as an active ingredient of a herbicide. SOLUTION: The present disclosure provides a heterocyclic amide compound represented by the following formula or a salt thereof. Q-N(R3)-C(=X)-W (Q: a substituted/unsubstituted 1,3,4-oxadiazole, 1,2,5-oxadiazole or the like. W: a substituted/unsubstituted [1,2,4]triazolo[4,3-a]pyridine or the like. X: O, S. R3: H, C1-C6 alkyl or the like). SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

ANTIBIOTIC COMPOUNDS

The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae.

The heterocyclic amide compound (by machine translation)

[Problem] an agrochemical, especially useful as a herbicide, the novel 1, 2, 4: triazolo 4,3-: pyridine-based compound. (1) the heterocyclic amide compound represented by the formula [a] and containing the herbicide. [Q may have a substituent can be an oxadiazole group, a tetrazole group, a triazole group, an oxazole group, an isoxazole group; W is a substituent group which may have 1, 2, 4: triazolo 4,3-: pyridine group][Drawing] no (by machine translation)