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【结 构 式】

【分子编号】55392

【品名】4-methyl-2-(methylamino)-1,3-thiazole-5-sulfonamide

【CA登记号】

【 分 子 式 】C5H9N3O2S2

【 分 子 量 】207.27748

【元素组成】C 28.97% H 4.38% N 20.27% O 15.44% S 30.94%

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)

The condensation of 2-(4-bromophenyl)acetic acid methyl ester (I) with 2-(trimethylstannyl)pyridine (II) by means of Pd(PPh3)4 in refluxing toluene gives 2-[4-(2-pyridyl)phenyl]acetic acid methyl ester (III), which is hydrolyzed with KOH in THF/water to yield the corresponding acetic acid (IV). Finally, this compound is condensed with 4-methyl-2-(methylamino)thiazole-5-sulfonamide (V) by means of HOBt and DEC in DMF to afford the target phenylacetamide. The intermediate 4-methyl-2-(methylamino)thiazole-5-sulfonamide (V) is obtained as follows: the reaction of 1-chloroacetone (VI) with KSCN in water gives the corresponding thiocyanato (VII), which is cyclized by means of dry HCl in dichloromethane to yield 2-chloro-4-methylthiazole (VIII). The reaction of (VIII) with Cl-SO3H and SOCl2 affords the sulfonyl chloride (IX), which is treated with ammonia in THF/water to provide 2-chloro-4-methylthiazole-5-sulfonamide (X). Finally, this compound is treated with methylamine in acetonitrile to obtain the target sulfonamide intermediate (V).

1 Fischer, R.; Bender, W.; Henninger, K.; Eckenberg, P.; Handke, G.; Keldenich, J.; Weber, O.; Kleymann, G.; Betz, U.; Hendrix, M.; Schneider, U.; Jensen, A.; Baumeister, J. (Bayer AG); Thiazolyl amide derivs.. DE 19962532; WO 0147904 .
2 Fischer, R.; Bender, W.; Henninger, K.; Eckenberg, P.; Handke, G.; Keldenich, J.; Weber, O.; Kleymann, G.; Betz, U.; Hendrix, M.; Schneider, U.; Jensen, A.; Baumeister, J.; Hewlett, G.; Pevzner, V. (Bayer AG); Incompetitive inhibitors of helicase primase. DE 10044353; WO 0220014 .
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) 16992 methyl 2-(4-bromophenyl)acetate 41841-16-1 C9H9BrO2 详情 详情
(II) 55389 2-Pyridyltrimethyltin; Trimethyl(2-pyridyl)tin 13737-05-8 C8H13NSn 详情 详情
(III) 55390 methyl 2-[4-(2-pyridinyl)phenyl]acetate C14H13NO2 详情 详情
(IV) 55391 2-[4-(2-pyridinyl)phenyl]acetic acid C13H11NO2 详情 详情
(V) 55392 4-methyl-2-(methylamino)-1,3-thiazole-5-sulfonamide C5H9N3O2S2 详情 详情
(VI) 15288 1-Chloroacetone; Chloroacetone 78-95-5 C3H5ClO 详情 详情
(VII) 55393 2-oxo-1-propanesulfenyl cyanide C4H5NOS 详情 详情
(VIII) 55394 2-chloro-4-methyl-1,3-thiazole C4H4ClNS 详情 详情
(IX) 55395 2-chloro-4-methyl-1,3-thiazole-5-sulfonyl chloride C4H3Cl2NO2S2 详情 详情
(X) 55396 2-chloro-4-methyl-1,3-thiazole-5-sulfonamide C4H5ClN2O2S2 详情 详情
Extended Information