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【结 构 式】

【分子编号】57021

【品名】6-methoxy-7-[3-(1-piperidinyl)propoxy]-4-quinazolinol

【CA登记号】

【 分 子 式 】C17H23N3O3

【 分 子 量 】317.38804

【元素组成】C 64.33% H 7.3% N 13.24% O 15.12%

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:(VIII)

The condensation of 4-hydroxy-3-methoxybenzoic acid ethyl ester (I) with 3-chloropropyl bromide (II) by means of K2CO3 in refluxing DMF gives the 4(3-chloropropoxy)-3-methoxybenzoic acid ethyl ester (III), which is nitrated by means of HNO3 and AcOH to yield the 2-nitro derivative (IV). The condensation of (IV) with piperidine (V) by means of K2CO3 in hot toluene affords 5-methoxy-2-nitro-4-[3-(1-piperidinyl)propoxy]benzoic acid ethyl ester (VI), which is reduced by means of Pd/C and HCO2K in ethanol/water to provide the 2-amino derivative (VII). The cyclization of (VII) with formamide and ammonium formate at 135 C gives the quinazoline (VIII), which is treated with SOCl2 in refluxing toluene to yield the chloro derivative (IX). Finally this compound is condensed with the piperazinecarboxamide (X) by means of K2CO3 in hot DMF/toluene to afford the target CT-53518.

1 Pandey, A.; et al.; Identification of orally active, potent, and selective 4-piperazinylquinazolines as antagonists of the platelet-derived growth factor receptor tyrosine kinase family. J Med Chem 2002, 45, 17, 3772.
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) 57016 3-Methoxy-4-hydroxybenzoic acid ethyl ester; 4-Hydroxy-3-methoxybenzoic acid ethyl ester; Ethyl 4-hydroxy-3-methoxybenzoate; Ethyl vanillate; Ethyl-3-Methoxy-4-Hydroxybenzoate; Vanillic acid ethyl ester 617-05-0 C10H12O4 详情 详情
(II) 10358 1-Bromo-3-chloropropane 109-70-6 C3H6BrCl 详情 详情
(III) 57017 ethyl 4-(3-chloropropoxy)-3-methoxybenzoate C13H17ClO4 详情 详情
(IV) 57018 ethyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate C13H16ClNO6 详情 详情
(V) 10158 Piperidine 110-89-4 C5H11N 详情 详情
(VI) 57019 ethyl 5-methoxy-2-nitro-4-[3-(1-piperidinyl)propoxy]benzoate C18H26N2O6 详情 详情
(VII) 57020 ethyl 2-amino-5-methoxy-4-[3-(1-piperidinyl)propoxy]benzoate C18H28N2O4 详情 详情
(VIII) 57021 6-methoxy-7-[3-(1-piperidinyl)propoxy]-4-quinazolinol C17H23N3O3 详情 详情
(IX) 57022 4-chloro-6-methoxy-7-[3-(1-piperidinyl)propoxy]quinazoline; 4-chloro-6-methoxy-7-quinazolinyl 3-(1-piperidinyl)propyl ether C17H22ClN3O2 详情 详情
(X) 57023 N-(4-isopropoxyphenyl)-1-piperazinecarboxamide C14H21N3O2 详情 详情
Extended Information