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【结 构 式】

【分子编号】38462

【品名】6-fluoro-2-methyl-4H-3,1-benzoxazin-4-one

【CA登记号】

【 分 子 式 】C9H6FNO2

【 分 子 量 】179.1505832

【元素组成】C 60.34% H 3.38% F 10.6% N 7.82% O 17.86%

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:(II)

Hydrogenation of 2-nitro-5-fluorobenzoic acid (I), followed by in situ condensation with acetic anhydride produced benzoxazinone (II). Subsequent reaction of (III) with 2-chloroaniline (III) in refluxing AcOH furnished quinazolinone (IV). Treatment of (IV) with 2,6-pyridinedicarboxaldehyde (V) in the presence of ZnCl2 and Ac2O gave rise to the pyridinylvinyl derivative (VI). The title amine was finally obtained by reductive amination of aldehyde (VI) with diethylamine using NaBH(OAc)3). The two atropisomers were separated by means of preparative chiral HPLC.

1 Ewing, F.E.; Welch, W.M.; Huang, J.; et al.; Atropisomeric quinazolin-4-one derivatives are potent noncompetitive alpha-amino-3-hydroxy-5-ethyl-4-isoxazolepropionic acid (AMPA) receptor antagonists. Bioorg Med Chem Lett 2001, 11, 2, 177.
2 Elliott, M.L.; Welch, W.M. Jr. (Pfizer Inc.); Novel 2,3 disubstd.-4(3H)-quinazolinones. EP 0901487; JP 1999514663; WO 9743276 .
3 Welch, W.M. Jr.; DeVries, K.M. (Pfizer Inc.); Atropisomers of 3-aryl-4(3H)-quinazolinones and their use as AMPA-receptor antagonists. EP 0968194; JP 2000509731; WO 9838173 .
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) 31962 2-Nitro-5-fluorobenzoic acid; 5-Fluoro-2-nitrobenzoic acid 320-98-9 C7H4FNO4 详情 详情
(II) 38462 6-fluoro-2-methyl-4H-3,1-benzoxazin-4-one C9H6FNO2 详情 详情
(III) 35804 2-chloroaniline; 2-chlorophenylamine 95-51-2 C6H6ClN 详情 详情
(IV) 38463 3-(2-chlorophenyl)-6-fluoro-2-methyl-4(3H)-quinazolinone C15H10ClFN2O 详情 详情
(V) 38464 2,6-pyridinedicarbaldehyde 5431-44-7 C7H5NO2 详情 详情
(VI) 38465 6-[(E)-2-[3-(2-chlorophenyl)-6-fluoro-4-oxo-3,4-dihydro-2-quinazolinyl]ethenyl]-2-pyridinecarbaldehyde C22H13ClFN3O2 详情 详情
Extended Information