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【结 构 式】

【分子编号】52190

【品名】N-{[(2-cyano-4,5-dimethoxyphenyl)imino][4-(2-furoyl)-1-piperazinyl]methyl}benzamide

【CA登记号】

【 分 子 式 】C26H25N5O5

【 分 子 量 】487.5152

【元素组成】C 64.06% H 5.17% N 14.37% O 16.41%

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:(VI)

Treatment of carboxy polystyrene resin (I) with oxalyl chloride in dichloromethane, followed by reaction with Bu4NNCS in THF/DCM, affords isothiocyanate resin (II), to which 2-amino-4,5-dimethoxybenzonitrile (III) is attached by means of NMP to provide derivative (IV). Treatment of resin (IV) with 1-(2-furoyl)-piperazine (V) and EDC in chloroform in the presence of DIEA furnishes resin-bound guanidine (VI), from which prazosin is obtained as its trifluoroacetic acid salt (VII) by acidolysis with TFA/H2O at 80 C. Finally, the hydrochloride salt of prazosin can be obtained by treatment with HCl.

1 Wilson, L.J.; Traceless solid-phase synthesis of 2,4-diaminoquinazolines. Org Lett 2001, 3, 4, 585.
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) 10202 Benzoic acid 65-85-0 C7H6O2 详情 详情
(II) 23530 benzoyl isothiocyanate 532-55-8 C8H5NOS 详情 详情
(III) 13038 2-Amino-4,5-dimethoxybenzonitrile 26961-27-3 C9H10N2O2 详情 详情
(IV) 52189 N-benzoyl-N'-(2-cyano-4,5-dimethoxyphenyl)thiourea C17H15N3O3S 详情 详情
(V) 30751 2-furyl(1-piperazinyl)methanone; 2-Furoyl-1-piperazine 40172-95-0 C9H12N2O2 详情 详情
(VI) 52190 N-{[(2-cyano-4,5-dimethoxyphenyl)imino][4-(2-furoyl)-1-piperazinyl]methyl}benzamide C26H25N5O5 详情 详情
(VII) 52191 [4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1-piperazinyl](2-furyl)methanone C19H21N5O4 详情 详情
Extended Information