1-chloro-6-methoxy-4-nitro-9H-thioxanthen-9-one -Drug Synthesis Database

【结构式】

【分子编号】52816

【品名】1-chloro-6-methoxy-4-nitro-9H-thioxanthen-9-one

【CA登记号】

【分子式】C₁₄H₈ClNO₄S

【分子量】321.74056

【元素组成】C 52.26% H 2.51% Cl 11.02% N 4.35% O 19.89% S 9.97%

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：(IV)

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.

参考文献中间体

合成目标

【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