4970-53-0

Usage

Uses

Used in Pharmaceutical Research and Development:
5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER is used as a building block in the synthesis of pharmaceutical compounds for its unique chemical structure and versatile reactivity, contributing to the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER is utilized as a key intermediate, facilitating the creation of complex organic molecules and contributing to advancements in chemical research.
Used in Antimicrobial Applications:
5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER is studied for its potential antimicrobial activities, suggesting its use as an antimicrobial agent in the development of treatments for various infections.
Used in Anticancer Research:
5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER is also being investigated for its potential anticancer activities, making it a candidate for further research in the development of cancer therapeutics, where it could be used to target and inhibit the growth of cancer cells.
Used in Drug Delivery Systems:
5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER may be employed in the design of drug delivery systems to improve the bioavailability and therapeutic efficacy of pharmaceutical agents, particularly in the context of its potential antimicrobial and anticancer properties.

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

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

Downstream Products

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

Relevant academic research and scientific papers

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

HETEROCYCLIC AMIDE COMPOUND

PROBLEM TO BE SOLVED: To provide a herbicide that reliably has an effect on various weeds at a reduced dosage, has reduced trouble such as soil pollution and influence on succeeding crops, and is highly safe. SOLUTION: The present invention provides a heterocyclic amide compound represented by the following formula and a herbicide containing the same. 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.

HETEROCYCLIC AMIDO COMPOUND

PROBLEM TO BE SOLVED: To provide a novel pesticide, especially a herbicide. SOLUTION: There are provided a heterocycle amide compound such as 3-isopropyl-N-(5-methyl-1, 3, 4-oxadiazole-2-yl)-5-(trifluoromethyl)-[1, 2, 4]triazolo [4,3-a] pyridine-8-carboxamide (compound No.1-004), 3-isopropyl-N-(5-methyl-1, 3, 4-oxadiazole-2-yl)-5-(methylthio)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxamide (compound No.1-009), and a herbicide containing them. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

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)