3-([[5-(aminocarbonyl)-1-methyl-3-propyl-1H-pyrazol-4-yl]amino]carbonyl)-4-propoxybenzenesulfonyl chloride -Drug Synthesis Database

【结构式】

【分子编号】50254

【品名】3-([[5-(aminocarbonyl)-1-methyl-3-propyl-1H-pyrazol-4-yl]amino]carbonyl)-4-propoxybenzenesulfonyl chloride

【CA登记号】

【分子式】C₁₈H₂₃ClN₄O₅S

【分子量】442.92328

【元素组成】C 48.81% H 5.23% Cl 8% N 12.65% O 18.06% S 7.24%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

The reaction of 2-propoxybenzoic acid (I) with SOCl2 in refluxing dichloromethane gives the acyl chloride (II), which is condensed with 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide (III) by means of TEA and DMAP in dichloromethane to yield the carboxamide (IV). The sulfonation of (IV) with chlorosulfonic acid affords the benzenesulfonyl chloride (V), which is treated with 2-(1-methylpyrrolidin-2-yl)ethylamine (VI) in dichloromethane to afford the sulfonamide (VII). Finally, this compound is cyclized by means of tBu-OK in refluxing tert-butanol to provide the target pyrazolo-pyrimidininone.

参考文献中间体

合成目标

【1】 Kim, S.-H.; Chang, M.-S.; Kim, D.-S.; Yoo, M.-H.; Kim, W.-B.; Bae, C.-J.; Kim, Y.-D.; Kim, E.-H. (Dong-A Pharmaceutical Co., Ltd.); A process for preparing pyrazolopyrimidinone derivs. for the treatment of impotence. WO 0198304 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	53952	2-n-Propoxybenzoic acid	2100-31-4	C₁₀H₁₂O₃	详情	详情
(II)	53953	2-propoxybenzoyl chloride		C₁₀H₁₁ClO₂	详情	详情
(III)	15627	4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide; 4-amino-1-methyl-3-propyl-5-pyrazolecarboxamide	139756-02-8	C₈H₁₄N₄O	详情	详情
(IV)	50253	1-methyl-4-[(2-propoxybenzoyl)amino]-3-propyl-1H-pyrazole-5-carboxamide		C₁₈H₂₄N₄O₃	详情	详情
(V)	50254	3-([[5-(aminocarbonyl)-1-methyl-3-propyl-1H-pyrazol-4-yl]amino]carbonyl)-4-propoxybenzenesulfonyl chloride		C₁₈H₂₃ClN₄O₅S	详情	详情
(VI)	53954	2-(2-Aminoethyl)-1-methylpyrrolidine	n/a	C₇H₁₆N₂	详情	详情
(VII)	53955	1-methyl-4-{[5-({[2-(1-methyl-2-pyrrolidinyl)ethyl]amino}sulfonyl)-2-propoxybenzoyl]amino}-3-propyl-1H-pyrazole-5-carboxamide		C₂₅H₃₈N₆O₅S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

Chlorosulfonylation of the benzamidopyrazole (I) to give (II) was performed with neat chlorosulfonic acid at 0 C. Coupling of sulfonyl chloride (II) with the piperidinopropanoate (III) provided sulfonamide (IV). Finally, cyclization of (IV) with concomitant ester hydrolysis under basic conditions furnished the target pyrazolopyrimidine.

参考文献中间体

合成目标

【1】 Kim, D.-K.; et al.; Synthesis and phosphodiesterase inhibitory activity of new sildenafil analogues containing a carboxylic acid group in the 5'-sulfonamide moiety of a phenyl ring. Bioorg Med Chem 2001, 9, 11, 3013.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	50253	1-methyl-4-[(2-propoxybenzoyl)amino]-3-propyl-1H-pyrazole-5-carboxamide	C₁₈H₂₄N₄O₃	详情	详情
(II)	50254	3-([[5-(aminocarbonyl)-1-methyl-3-propyl-1H-pyrazol-4-yl]amino]carbonyl)-4-propoxybenzenesulfonyl chloride	C₁₈H₂₃ClN₄O₅S	详情	详情
(III)	50255	ethyl 3-(4-piperidinyl)propanoate	C₁₀H₁₉NO₂	详情	详情
(IV)	50256	ethyl 3-(1-[[3-([[5-(aminocarbonyl)-1-methyl-3-propyl-1H-pyrazol-4-yl]amino]carbonyl)-4-propoxyphenyl]sulfonyl]-4-piperidinyl)propanoate	C₂₈H₄₁N₅O₇S	详情	详情

Extended Information