2-chloro-5-cyano-4-[(2-thienylmethyl)amino]benzenesulfonamide -Drug Synthesis Database

【结构式】

【分子编号】33239

【品名】2-chloro-5-cyano-4-[(2-thienylmethyl)amino]benzenesulfonamide

【CA登记号】

【分子式】C₁₂H₁₀ClN₃O₂S₂

【分子量】327.81512

【元素组成】C 43.97% H 3.07% Cl 10.81% N 12.82% O 9.76% S 19.56%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VI)

The reaction of 2-fluoro-4-chloro-5-sulfamoylbenzoic acid (I) with refluxing SOCl2 gives the corresponding acyl chloride (II), which by reaction with aqueous NH3 is transformed into the amide (III). The dehydration of (III) with refluxing POCl3 affords the nitrile (IV), which is then condensed with thenylamine (V) to yield 4-chloro-2-thenylamino-5-sulfamoylbenzonitrile (VI). Finally, this compound is cyclized with sodium azide in DMF at 100 C.

参考文献中间体

合成目标

【1】 Popelak, A.; et al. (Boehringer Ingelheim GmbH); 5-Phenyltetrazole derivatives. DE 1815922; FR 2026688; GB 1237790; US 3665002 .
【2】 Serradell, M.N.; Castaner, J.; Blancafort, P.; Hillier, K.; Azosemide. Drugs Fut 1979, 4, 6, 393.

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)	33234	5-(aminosulfonyl)-4-chloro-2-fluorobenzoic acid		C₇H₅ClFNO₄S	详情	详情
(II)	33235	5-(aminosulfonyl)-4-chloro-2-fluorobenzoyl chloride		C₇H₄Cl₂FNO₃S	详情	详情
(III)	33236	5-(aminosulfonyl)-4-chloro-2-fluorobenzamide		C₇H₆ClFN₂O₃S	详情	详情
(IV)	33237	2-chloro-5-cyano-4-fluorobenzenesulfonamide		C₇H₄ClFN₂O₂S	详情	详情
(V)	33238	2-thienylmethylamine; 2-thienylmethanamine	27757-85-3	C₅H₇NS	详情	详情
(VI)	33239	2-chloro-5-cyano-4-[(2-thienylmethyl)amino]benzenesulfonamide		C₁₂H₁₀ClN₃O₂S₂	详情	详情

Extended Information