• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】57843

【品名】2-(3-chlorophenyl)-1-(2,2-diethoxyethyl)-6-oxo-1,6-dihydro-5-pyrimidinecarboxylic acid

【CA登记号】

【 分 子 式 】C17H19ClN2O5

【 分 子 量 】366.80104

【元素组成】C 55.67% H 5.22% Cl 9.67% N 7.64% O 21.81%

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:(XVI)

The reaction of 3-chlorobenzonitrile (X) with HCl and ethanol gives the ethyl 3-chlorobenzimidate (XI), which is condensed with 2-aminoacetaldehyde diethylacetal (XII) in ethanol to yield 3-chloro-N-(2,2-diethoxyethyl)benzamidine (XIII). The cyclization of (XIII) with diethyl ethoxymethylenemalonate (XIV) in refluxing ethanol affords the pyrimidinone (XV), the ester group of which is hydrolyzed with LiI and NaHCO3 in pyridine to provide the corresponding carboxylic acid (XVI). The reaction of the carboxylic group of (XVI) with DPPA and TEA in refluxing dioxane gives the N-benzyloxycarbonylamino-pyrimidinone (XVII). The hydrolysis of he diethylacetal group of (XVII) with hot 1M HCl yields the acetaldehyde derivative (XVIII), which is oxidized with NaClO2 in water to afford the acetic acid derivative (XIX). The condensation of (XIX) with the already reported intermediate (IX) by means of HOBt and WSC provides the amide (XX), which is finally deprotected by means of trifluromethanesulfonic acid and anisole in dichloromethane to yield the target diamide derivative.

1 Kobayashi, F.; Naito, K.; Yoshikawa, T.; Kuwahara, S.; Imada, T.; Komorita, N. (Mitsubishi Pharma Corp.); IgE antibody production inhibitors and autoimmune diseases inhibitors. EP 1062949; US 6528514; WO 9945928 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IX) 57839 4-amino-N-benzyl-2,2-difluoro-5-phenylpentanamide C18H20F2N2O 详情 详情
(X) 33570 3-chlorobenzonitrile 766-84-7 C7H4ClN 详情 详情
(XI) 57840 ethyl 3-chlorobenzenecarboximidoate C9H10ClNO 详情 详情
(XII) 10331 2,2-Diethoxy-1-ethanamine; 2,2-Diethoxyethylamine; Aminoacetaldehyde diethyl acetal 645-36-3 C6H15NO2 详情 详情
(XIII) 57841 3-chloro-N-(2,2-diethoxyethyl)benzenecarboximidamide C13H19ClN2O2 详情 详情
(XIV) 14088 Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate 87-13-8 C10H16O5 详情 详情
(XV) 57842 methyl 2-(3-chlorophenyl)-1-(2,2-diethoxyethyl)-6-oxo-1,6-dihydro-5-pyrimidinecarboxylate C18H21ClN2O5 详情 详情
(XVI) 57843 2-(3-chlorophenyl)-1-(2,2-diethoxyethyl)-6-oxo-1,6-dihydro-5-pyrimidinecarboxylic acid C17H19ClN2O5 详情 详情
(XVII) 57844 benzyl 2-(3-chlorophenyl)-1-(2,2-diethoxyethyl)-6-oxo-1,6-dihydro-5-pyrimidinylcarbamate C24H26ClN3O5 详情 详情
(XVIII) 57845 benzyl 2-(3-chlorophenyl)-6-oxo-1-(2-oxoethyl)-1,6-dihydro-5-pyrimidinylcarbamate C20H16ClN3O4 详情 详情
(XIX) 57846 2-[5-{[(benzyloxy)carbonyl]amino}-2-(3-chlorophenyl)-6-oxo-1(6H)-pyrimidinyl]acetic acid C20H16ClN3O5 详情 详情
(XX) 57847 benzyl 1-(2-{[1-benzyl-4-(benzylamino)-3,3-difluoro-4-oxobutyl]amino}-2-oxoethyl)-2-(3-chlorophenyl)-6-oxo-1,6-dihydro-5-pyrimidinylcarbamate C38H34ClF2N5O5 详情 详情
Extended Information