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【结 构 式】

【分子编号】18689

【品名】4-(3-chloro-4-fluoroanilino)-7-methoxy-6-quinazolinyl acetate

【CA登记号】788136-89-0

【 分 子 式 】C17H13ClFN3O3

【 分 子 量 】361.7597432

【元素组成】C 56.44% H 3.62% Cl 9.8% F 5.25% N 11.62% O 13.27%

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)

Monodemethylation of 6,7-dimethoxyquinazolin-4(3H)-one (I) in refluxing methanesulfonic acid in the presence of L-methionine provides 6-hydroxy-7-methoxyquinazolin-4(3H)-one (II), which is acetylated with acetic anhydride and pyridine at 100 C to give the acetate (III). Treatment of compound (III) with refluxing SOCl2 and a catalytic amount of DMF yields chloride (IV), which by condensation with 3-chloro-4-fluoroaniline (V) in boiling isopropanol affords the anilinoquinazoline (VI). Hydrolysis of the acetate group of (VI) by treatment with NH4OH in refluxing MeOH gives the 6-hydroxyquinazoline derivative (VII), which finally is alkylated with 3-(4-morpholinyl)-propyl chloride (VIII) or 3-(4-morpholinyl)propyl bromide (IX).

1 Gibson, K.H.; Grundy, W.; Barker, A.J.; et al.; Studies leading to the identification of ZD1839 (Iressa(TM)): An orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer. Bioorg Med Chem Lett 2001, 11, 14, 1911.
2 D'Souza, N.; Castañer, J.; Levin, M.; Iressa. Drugs Fut 2002, 27, 4, 339.
3 Gibson, K.H. (AstraZeneca plc); Quinazoline derivs.. EP 0823900; JP 1999504033; US 5770599; WO 9633980 .
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) 18684 6,7-dimethoxy-4(3H)-quinazolinone 13794-72-4 C10H10N2O3 详情 详情
(II) 18685 6-hydroxy-7-methoxy-4(3H)-quinazolinone 179688-52-9 C9H8N2O3 详情 详情
(III) 18686 7-methoxy-4-oxo-3,4-dihydro-6-quinazolinyl acetate 179688-53-0 C11H10N2O4 详情 详情
(IV) 18687 4-chloro-7-methoxy-6-quinazolinyl acetate 230955-75-6 C11H9ClN2O3 详情 详情
(V) 18688 3-Chloro-4-fluorophenylamine; 3-Chloro-4-fluoroaniline 367-21-5 C6H5ClFN 详情 详情
(VI) 18689 4-(3-chloro-4-fluoroanilino)-7-methoxy-6-quinazolinyl acetate 788136-89-0 C17H13ClFN3O3 详情 详情
(VII) 18690 4-(3-chloro-4-fluoroanilino)-7-methoxy-6-quinazolinol 184475-71-6 C15H11ClFN3O2 详情 详情
(VIII) 18691 4-(3-chloropropyl)morpholine;N-(3-Chloropropyl)morpholine 7357-67-7 C7H14ClNO 详情 详情
(IX) 52653 4-(3-bromopropyl)morpholine 125422-83-5 C7H14BrNO 详情 详情
Extended Information