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【结 构 式】

【分子编号】52820

【品名】N-(2-aminoethyl)-N-{2-[2-(diethylamino)ethyl]-8-methoxy-2H-thiochromeno[4,3,2-cd]indazol-5-yl}amine; N~1~-{2-[2-(diethylamino)ethyl]-8-methoxy-2H-thiochromeno[4,3,2-cd]indazol-5-yl}-1,2-ethanediamine

【CA登记号】

【 分 子 式 】C22H29N5OS

【 分 子 量 】411.57136

【元素组成】C 64.2% H 7.1% N 17.02% O 3.89% S 7.79%

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:(IX)

The condensation of 3-methoxybenzenethiol (I) with 2,6-dichloro-3-nitrobenzoic acid (II) produced the (arylthio)benzoic acid (III). Intramolecular cyclization of (III) to the thioxanthenone (IV) was effected by treatment with trifluoroacetic anhydride in trifluoroacetic acid. The pentacyclic system (VI) was prepared by condensation of chloroxanthenone (IV) with 2-(diethylamino)ethyl hydrazine (V). Subsequently, the nitro group of (IV) was reduced with H2 in the presence of Pd/C to furnish amine (VII). This was alkylated with 2-bromoethylamine (VIII), yielding the ethylenediamine derivative (IX). The methyl ether group of (IX) was finally cleaved by treatment with boron tribromide.

1 Showalter, H.D.H.; Werbel, L.M.; Ortwine, D.F.; Eislager, E.F.; Worth, D.F. (Pfizer Inc.); Benzothiopyrano[4,3,2-cd]indazole compsns. and methods for their production. EP 0114002; ES 8600303; ES 8604229; ES 8604230; JP 1994279385; US 4604390 .
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) 25756 3-methoxybenzenethiol 15570-12-4 C7H8OS 详情 详情
(II) 52274 2,5-Dichloro-3-nitrobenzoic acid 88-86-8 C7H3Cl2NO4 详情 详情
(III) 52815 6-chloro-2-[(3-methoxyphenyl)sulfanyl]-3-nitrobenzoic acid C14H10ClNO5S 详情 详情
(IV) 52816 1-chloro-6-methoxy-4-nitro-9H-thioxanthen-9-one C14H8ClNO4S 详情 详情
(V) 52817 N,N-diethyl-2-hydrazino-1-ethanamine; N,N-diethyl-N-(2-hydrazinoethyl)amine C6H17N3 详情 详情
(VI) 52818 N,N-diethyl-2-(8-methoxy-5-nitro-2H-thiochromeno[4,3,2-cd]indazol-2-yl)-1-ethanamine; N,N-diethyl-N-[2-(8-methoxy-5-nitro-2H-thiochromeno[4,3,2-cd]indazol-2-yl)ethyl]amine C20H22N4O3S 详情 详情
(VII) 52819 2-[2-(diethylamino)ethyl]-8-methoxy-2H-thiochromeno[4,3,2-cd]indazol-5-amine; N-[2-(5-amino-8-methoxy-2H-thiochromeno[4,3,2-cd]indazol-2-yl)ethyl]-N,N-diethylamine C20H24N4OS 详情 详情
(VIII) 38475 2-bromoethylamine; 2-bromo-1-ethanamine C2H6BrN 详情 详情
(IX) 52820 N-(2-aminoethyl)-N-{2-[2-(diethylamino)ethyl]-8-methoxy-2H-thiochromeno[4,3,2-cd]indazol-5-yl}amine; N~1~-{2-[2-(diethylamino)ethyl]-8-methoxy-2H-thiochromeno[4,3,2-cd]indazol-5-yl}-1,2-ethanediamine C22H29N5OS 详情 详情
Extended Information