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【结 构 式】 
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【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% |
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 |