Synthesizing darolutamide intermediate comprises reacting 2-chlorotoluene with acetyl chloride, reacting 1-(3-chloro-4-methylphenyl) ethan-1-one with dimethylformamide-dimethyl acetamide, cyclizing, oxidizing, followed by dehydrating 2-chloro-4-(1H-pyrazol-3-yl)benzamide
	TIWARI I K; RACHAKONDA V; RACHAKONDA S
	2024-07-24
专利权人	TYLON PHARMA LTD (TYLO-Non-standard) ; TYLON PHARMA PTE LTD (TYLO-Non-standard) ; VCS CHEM TECH PVT LTD (VCSC-Non-standard)
申请日期	2024-07-24
专利号	IN202441056287-A
成果简介	NOVELTY - Synthesizing darolutamide intermediate (I) comprises: (i) subjecting 4-bromo-2-chlorobenzamide (VI) to dehydration reaction to obtain 4-bromo-2-chiorobenzonitrile (II); (ii) reacting 2-chloro toluene with acetyl chloride to obtain 1-(3-chloro-4-methylphenyl) ethan-1-one (VII); (iii) reacting compound (VII) with dimethylformamide-dimethyl acetamide to obtain 1-(3-chloro-4-methylphenyI)-3-(dimethylamino)prop-2-en-1-one (VIII), followed by performing cyclization/pyrazole formation with hydrazine hydrate to obtain 3-(3-chloro-4-methylphenyl)-1H-pyrazole (IX); (iv) subjecting compound (IX) to oxidation to obtain 2-chloro-4-(1H-pyrazol-3-yl) benzoic acid (X); (v) subjecting compound (X) to acid chloride formation to obtain 2-chloro-4-(1H-pyrazol-3-yl) benzoyl chloride (XI); (vi) subjecting compound (XI) to amidation reaction to obtain 2-chloro-4-(1H-pyrazol-3-yl) benzamide (XII); and (vii) subjecting compound (XII) to dehydration to obtain target compound (I). USE - Method for synthesizing darolutamide intermediate. ADVANTAGE - The method provides darolutamide intermediate in cost-effective manner. DETAILED DESCRIPTION - Synthesizing darolutamide intermediate of formula (I) comprises: (i) subjecting 4-bromo-2-chlorobenzamide of formula (VI) to dehydration reaction using phosphorus oxychloride or thionyl chloride and other dehydrating agent to obtain 4-bromo-2-chiorobenzonitrile of formula (II); (ii) reacting 2-chloro toluene with acetyl chloride and aluminum chloride in presence of dichloroethane to obtain 1-(3-chloro-4-methylphenyl) ethan-1-one of formula (VII); (iii) reacting compound (VII) with dimethylformamide-dimethyl acetamide to obtain 1-(3-chloro-4-methylphenyI)-3-(dimethylamino)prop-2-en-1-one of formula (VIII), followed by performing cyclization/pyrazole formation with hydrazine hydrate to obtain 3-(3-chloro-4-methylphenyl)-1H-pyrazole of formula (IX); (iv) subjecting compound (IX) to oxidation with potassium permanganate or chromium oxide to obtain 2-chloro-4-(1H-pyrazol-3-yl) benzoic acid of formula (X); (v) subjecting compound (X) to acid chloride formation with thionyl chloride or phosphorus oxychloride to obtain 2-chloro-4-(1H-pyrazol-3-yl) benzoyl chloride of formula (XI); (vi) subjecting compound (XI) to amidation reaction with ammonium hydroxide or ammonia gas to obtain 2-chloro-4-(1H-pyrazol-3-yl) benzamide of formula (XII); and (vii) subjecting compound (XII) to dehydration with thionyl chloride or phosphorus oxychloride to obtain target compound (I).
IPC 分类号	A61K-031/192 ; A61K-031/4155 ; A61K-009/00 ; C07H-019/073 ; C09K-011/77
国家	印度
专业领域	医药卫生
语种	英语
成果类型	专利
文献类型	科技成果
条目标识符	http://119.78.100.226:8889/handle/3KE4DYBR/15663
专题	中国科学院新疆生态与地理研究所
作者单位	1.TYLON PHARMA LTD (TYLO-Non-standard) 2.TYLON PHARMA PTE LTD (TYLO-Non-standard) 3.VCS CHEM TECH PVT LTD (VCSC-Non-standard)
推荐引用方式 GB/T 7714	TIWARI I K,RACHAKONDA V,RACHAKONDA S. Synthesizing darolutamide intermediate comprises reacting 2-chlorotoluene with acetyl chloride, reacting 1-(3-chloro-4-methylphenyl) ethan-1-one with dimethylformamide-dimethyl acetamide, cyclizing, oxidizing, followed by dehydrating 2-chloro-4-(1H-pyrazol-3-yl)benzamide. IN202441056287-A[P]. 2024.

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