5-ACETYL-1H-PYRAZOLE-3-카르복실산

한글명:5-ACETYL-1H-PYRAZOLE-3-카르복실산

카스 번호1297537-45-1

상품명:5-Acetyl-1H-Pyrazole-3-carboxylic acid

CBNumberCB5804520

분자식C6H6N2O3

포뮬러 무게154.12

MOL 파일Mol file

동의어(한글)

5-ACETYL-1H-PYRAZOLE-3-카르복실산

화학적 성질

녹는점	257-269 °C (decomp)(Solv: ethanol (64-17-5); benzene (71-43-2))
끓는 점	479.2±30.0 °C(Predicted)
밀도	1.467±0.06 g/cm3(Predicted)
저장 조건	2-8°C
산도 계수 (pKa)	3.60±0.10(Predicted)
InChI	InChI=1S/C6H6N2O3/c1-3(9)4-2-5(6(10)11)8-7-4/h2H,1H3,(H,7,8)(H,10,11)
InChIKey	HFBWRCZRDIVAMQ-UHFFFAOYSA-N
SMILES	N1C(C(C)=O)=CC(C(O)=O)=N1

그림문자(GHS)

5-ACETYL-1H-PYRAZOLE-3-카르복실산 화학적 특성, 용도, 생산

정의
5-Acetyl-1H-pyrazole-3-carboxylic acid can be considered a valuable building block for other types of organic and medicinal chemistry transformations and is the essential starting material for the preparation of Darolutamide, which is chemically known as N-{(2S)-1-[3-(3-chloro-4- cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-5-(1-hydroxyethyl)-1H-pyrazole-3- 10 carboxamide. Orion Corporation and Bayer Health Care developed Darolutamide. It is an anti-androgen medication that is used for the treatment of prostate cancer in men. Recently, a safe and metal-free process using ethyl glycinate hydrochloride as the starting material has been developed to prepare 5-Acetyl-1H-Pyrazole-3-carboxylic acid[1-2].
Synthesis
5-Acetyl-1H-pyrazole-3-carboxylic acid is a chemical compound that is synthesized from hydrazine and acetyl chloride.
Potassium tert-butoxide (102 g) was added lot-wise to the pre-cooled mixture of 3,3-dimethoxybutane-2-one (100 g) in toluene (1000 ml) at 5-10°C and stirred for 45 minutes. Diethyl oxalate (132 g) was added to the mixture at 10-15°C and stirred for 4 hours. Filtered the solid. To the filtered solid water (3000 ml) was added and cooled to 5-10°C. Solution of Hydrazine monohydrochloride (51.8 g) was slowly added to the mixture at 5-10°C and stirred for 4 hrs. Dichloromethane (1000 ml) was added to the mixture at 5-10°C and stirred for 15 minutes. Allowed to heat the mixture to 25-30°C and stirred for 15 minutes. Filtered the mixture through hyflow. Organic layer was separated from the filtrate. Distilled-off the organic layer and co-distilled in n-heptane (50 ml). n-heptane (300 ml) was added to the mixture at 25-30°C. Heated the mixture at 45-50°C and stirred for 1 hrs. Allowed to cool the mixture to 25-30°C and stirred for 3 hours. Filtered the solid. THF (150 ml) was added to the obtained solid. aq. Sodium hydroxide solution was added to the mixture at 10-15°C. Heated the mixture to 55-60°C and stirred for 2 hrs. Allowed to cool the mixture to 25-30°C and stirred for 15 minutes. Separated the aqueous layer from organic layer. Water was added to the aqueous layer at 25-30°C. Cooled the mixture to 20-25°C. Treated the mixture with hydrochloric acid at 20-25°C. Allowed to heat the mixture to 25-30°C and stirred for 4 hours. Filtered the solid and dried. Tetrahydrofuran (300 ml) was added to the obtained solid at 25-30°C. Heated the mixture to 50-55°C and stirred for 60 minutes. Allowed to cool the mixture to 25-30°C and stirred for 3 hours. Filtered the solid and dried to get 5-Acetyl-1H-pyrazole-3-carboxylic acid, Yield: 63 gm Purity by HPLC: 99.93%.

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