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【结 构 式】 
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【分子编号】48544 【品名】8-(methylsulfanyl)-6,8-dihydro-7H-[1,3]thiazolo[5,4-e]indol-7-one 【CA登记号】 |
【 分 子 式 】C10H8N2OS2 【 分 子 量 】236.3184 【元素组成】C 50.83% H 3.41% N 11.85% O 6.77% S 27.14% |
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)The condensation of 6-aminobenzothiazole (I) with ethyl 2-(methylsulfanyl)acetate (II) in the presence of tert-butyl hypochlorite produced the oxindole derivative (III). The methylsulfanyl group was then reductively removed using zinc in acetic acid to afford (IV). Reaction of (IV) with diethoxymethyl acetate in refluxing HOAc furnished the ethoxymethylene derivative (V). This was finally condensed with sulfapyridine (VI) to give the title compound.
| 【1】 Frye, S.V.; Davis, S.T.; Lackey, K.E.; Dickerson, S.H.; Luzzio, M.J.; Kuyper, L.F.; Veal, J.M.; Hunter, R.N. III; Walker, D.H.; Harris, P.A. (Glaxo Group Ltd.); Substd. oxindole derivs. as protein tyrosine kinase and as protein serine/threonine kinase inhibitors. EP 1009738; WO 9915500 . |
| 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) | 17908 | 1,3-benzothiazol-6-ylamine; 1,3-benzothiazol-6-amine; 6-Aminobenzothiazole | 533-30-2 | C7H6N2S | 详情 | 详情 |
| (II) | 48543 | Ethyl methylthioacetate; (Methylthio)acetic acid ethyl ester; ethyl 2-(methylsulfanyl)acetate | 4455-13-4 | C5H10O2S | 详情 | 详情 |
| (III) | 48544 | 8-(methylsulfanyl)-6,8-dihydro-7H-[1,3]thiazolo[5,4-e]indol-7-one | C10H8N2OS2 | 详情 | 详情 | |
| (IV) | 48545 | 6,8-dihydro-7H-[1,3]thiazolo[5,4-e]indol-7-one | C9H6N2OS | 详情 | 详情 | |
| (V) | 48546 | 8-[(Z)-ethoxymethylidene]-6H-[1,3]thiazolo[5,4-e]indol-7-one | C12H10N2O2S | 详情 | 详情 | |
| (VI) | 48547 | 2-(4-Aminobenzenesulfonamido)pyridine; 4-Amino-N-2-pyridylbenzenesulfonamide; Sulfapyridine | 144-83-2 | C11H11N3O2S | 详情 | 详情 |
Extended Information