163213-38-5

Basic information

• Product Name: METHYL 4-OXO-5,6,7,8-TETRAHYDRO-4H-PYRAZOLO[1,5-A][1,4]DIAZEPINE-2-CARBOXYLATE
• Synonyms: METHYL 4-OXO-5,6,7,8-TETRAHYDRO-4H-PYRAZOLO[1,5-A][1,4]DIAZEPINE-2-CARBOXYLATE;Methyl 4-oxo-5.6.7.8-tetrahydro-4H-pyrazolo[1.5-a][1.4]diazepine;Methyl 4-oxo-4H,5H,6H,7H,8H-pyrazolo-[1,5-a][1,4]diazepine-2-carboxylate
• CAS NO: 163213-38-5
• Molecular Formula: C₉H₁₁N₃O₃
• Molecular Weight: 209.2
• Mol File: 163213-38-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: METHYL 4-OXO-5,6,7,8-TETRAHYDRO-4H-PYRAZOLO[1,5-A][1,4]DIAZEPINE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-OXO-5,6,7,8-TETRAHYDRO-4H-PYRAZOLO[1,5-A][1,4]DIAZEPINE-2-CARBOXYLATE(163213-38-5)
• EPA Substance Registry System: METHYL 4-OXO-5,6,7,8-TETRAHYDRO-4H-PYRAZOLO[1,5-A][1,4]DIAZEPINE-2-CARBOXYLATE(163213-38-5)

Safety Data

• Hazardous Substances Data: 163213-38-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4-OXO-5,6,7,8-TETRAHYDRO-4H-PYRAZOLO[1,5-A][1,4]DIAZEPINE-2-CARBOXYLATE is used as a reagent for the preparation of pyrazolodiazepine fibrinogen receptor antagonists. These antagonists are important in the development of drugs targeting various medical conditions, such as thrombosis and other clot-related disorders. The compound's ability to interact with fibrinogen receptors makes it a valuable tool in the design and synthesis of novel therapeutic agents.

Upstream product

• 4077-76-3 3,5-dicarbomethoxypyrazole 
• 5003-71-4 3-bromopropylamine hydrochloride 
• 163213-37-4 dimethyl 1-(3-Azidopropyl)pyrazole-3,5-dicarboxylate 
• 166324-92-1 1-(3-Chloro-propyl)-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester 
• 3112-31-0 3,5-pyrazoledicarboxylic acid 

Downstream Products

• 251553-58-9 methyl [5,6,7,8-tetrahydro-4-oxo-5-[2-(pyridin-4-yl)ethyl]-4H-pyrazolo[1,5-a][1,4]diazepin-2-yl]carboxylate 
• 163213-77-2 4-(2-{2-[(S)-2-Carboxy-2-(toluene-4-sulfonylamino)-ethylcarbamoyl]-4-oxo-7,8-dihydro-4H,6H-1,5,8a-triaza-azulen-5-yl}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 163212-43-9 L 738167 
• 163213-40-9 5-[2-(1-tert-Butoxycarbonyl-piperidin-4-yl)-ethyl]-4-oxo-5,6,7,8-tetrahydro-4H-1,5,8a-triaza-azulene-2-carboxylic acid 
• 163213-39-6 5-[2-(1-tert-Butoxycarbonyl-piperidin-4-yl)-ethyl]-4-oxo-5,6,7,8-tetrahydro-4H-1,5,8a-triaza-azulene-2-carboxylic acid methyl ester 
• 251553-60-3 2(S)-[(p-toluenesulfonyl)amino]-3-[[[5,6,7,8-tetrahydro-4-oxo-5-[2-(pyridin-4-yl)ethyl]-4H-pyrazolo[1,5-a][1,4]diazepin-2-yl]carbonyl]amino]propionic acid benzyl ester 

Relevant articles and documents

Rapid synthesis of tetrahydro-4H-pyrazolo[1,5-a]diazepine-2-carboxylate

Hydrazines condense with dimethyl 2-pyrrolidino-4-oxo-2-pentenedioate in the presence of aq. HCl to form N-substituted pyrazole-3,5-dicarboxylates 2. Complex bicyclic derivatives, such as pyrazolo-oxazine 3a, pyrazolo-oxazepine 3b, pyrazolo-pyrazine 4a, and pyrazolo-diazepine 4b, were generated using 2-hydrazinoethanol, 3-hydrazinopropanol, 2-hydrazinoethylamine, and 3-hydrazinopropylamine.

A highly convergent synthesis of a fibrinogen receptor antagonist

A practical multikilogram synthesis of 2(S)-[(p-toluenesulfonyl)amino]- 3-[[[5,6,7,8-tetrahydro-4-oxo-5-[2-(piperidin-4-yl)ethyl]-4H-pyrazolo[1,5- α][1,4]diazepin-2-yl]carbonyl]amino]propionic acid pentahydrate (1), an oral fibrinogen receptor antagonist, is described. The nine-step convergent process, which afforded 1 in 37% overall yield, included pyrazole 5a and N- tosylaminoalanine 16 as key fragments. Pyrazole 5a was obtained from pyrazole-3,5-dicarboxylic acid by esterification with MeOH, alkylation/cyclization with 3-bromopropylamine, and Michael addition with 4- vinylpyridine. N-Tosylaminoalanine 16 was prepared by tosylation of asparagine, Hofmann reaction, and benzyl esterification. Saponification of pyrazole 5a, coupling of the acid with N-tosylaminoalanine 16, and Pd- catalyzed hydrogenolysis and pyridine reduction completed the synthesis.

Non-peptide glycoprotein IIb/IIIa inhibitors. 17. Design and synthesis of orally active, long-acting non-peptide fibrinogen receptor antagonists

The synthesis and pharmacological evaluation of 5 (L-738,167), a potent, selective non-peptide fibrinogen receptor antagonist is reported. Compound 5 inhibited the aggregation of human gel-filtered platelets with an IC50 value of 8 nM and was found to be >33000-fold less effective at inhibiting the attachment of human endothelial cells to fibrinogen, fibronectin, and vitronectin than it was at inhibiting platelet aggregation. Ex vivo platelet aggregation was inhibited by >85% 24 h after the oral administration of 5 to dogs at 100 μg/kg. The extended pharmacodynamic profile exhibited by 5 appears to be a consequence of its high-affinity binding to GPIIb/IIIa on circulating platelets and suggests that 5 is suitable for once-a-day dosing.