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【结 构 式】

【分子编号】61489

【品名】3-amino-N-(tert-butyl)-5-chloro-2-thiophenesulfonamide

【CA登记号】

【 分 子 式 】C8H13ClN2O2S2

【 分 子 量 】268.7882

【元素组成】C 35.75% H 4.87% Cl 13.19% N 10.42% O 11.9% S 23.86%

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:(III)

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

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 CAS号 分子式 供应商 用于合成
(I) 61487 N-(tert-butyl)-5-chloro-2-thiophenesulfonamide C8H12ClNO2S2 详情 详情
(II) 61488 3-azido-N-(tert-butyl)-5-chloro-2-thiophenesulfonamide C8H11ClN4O2S2 详情 详情
(III) 61489 3-amino-N-(tert-butyl)-5-chloro-2-thiophenesulfonamide C8H13ClN2O2S2 详情 详情
(IV) 61490 3-amino-5-chloro-2-thiophenesulfonamide C4H5ClN2O2S2 详情 详情
(V) 61491 3-amino-5-chloro-2-({[(isopropylamino)carbothioyl]amino}sulfonyl)thiophene C8H12ClN3O2S3 详情 详情
Extended Information