methyl 5-chloro-2-({[(isopropylamino)carbothioyl]amino}sulfonyl)-3-thienylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】61495

【品名】methyl 5-chloro-2-({[(isopropylamino)carbothioyl]amino}sulfonyl)-3-thienylcarbamate

【CA登记号】

【分子式】C₁₀H₁₄ClN₃O₄S₃

【分子量】371.88968

【元素组成】C 32.3% H 3.79% Cl 9.53% N 11.3% O 17.21% S 25.87%

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：(V)

In an alternative procedure, metalation of thiophenesulfonamide (I) with butyllithium, followed by quenching with p-toluenesulfonyl azide affords azide (II), which is further reduced to amine (III) with NaBH4 in the presence of a quaternary phosphonium salt. The N-t-butyl group of (III) is then cleaved with fuming HCl to afford (IV). Condensation of sulfonamide (IV) with isopropyl isothiocyanate furnishes the sulfonyl thiourea (V). This is finally cyclized to the desired thienothiadiazine by treatment with phosgene in the presence of triethylamine

参考文献中间体

合成目标

【1】 Nielsen, F.E.; Bodvarsdottir, T.B.; Worsaae, A.; et al.; 6-Chloro-3-alkylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide derivatives potently and selectively activate ATP sensitive potassium channels of pancreatic beta-cells. J. Med. Chem. 2002, 45, 19, 4171.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	61482	2-[(tert-butylamino)sulfonyl]-5-chloro-3-thiophenecarboxylic acid	C₉H₁₂ClNO₄S₂	详情	详情
(II)	61492	ethyl 2-[(tert-butylamino)sulfonyl]-5-chloro-3-thiophenecarboxylate	C₁₁H₁₆ClNO₄S₂	详情	详情
(III)	61493	N-(tert-butyl)-5-chloro-3-(hydrazinocarbonyl)-2-thiophenesulfonamide	C₉H₁₄ClN₃O₃S₂	详情	详情
(IV)	61494	methyl 2-(aminosulfonyl)-5-chloro-3-thienylcarbamate	C₆H₇ClN₂O₄S₂	详情	详情
(V)	61495	methyl 5-chloro-2-({[(isopropylamino)carbothioyl]amino}sulfonyl)-3-thienylcarbamate	C₁₀H₁₄ClN₃O₄S₃	详情	详情
(VI)	61496	methyl 6-chloro-3-(isopropylamino)-1,1-dioxo-1lambda~6~-thieno[3,2-e][1,2,4]thiadiazine-4(1H)-carboxylate	C₁₀H₁₂ClN₃O₄S₂	详情	详情

Extended Information