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【结 构 式】

【分子编号】68042

【品名】(E)-methyl 3-(3-fluoro-2-(3-(2-methoxy-5-(trifluoromethyl)phenyl)ureido)phenyl)acrylate

【CA登记号】 

【 分 子 式 】C19H16F4N2O4

【 分 子 量 】412.341

【元素组成】C 55.34% H 3.91% F 18.43% N 6.79% O 15.52%

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:(XVII)

Condensation of 2-fluoroaniline (XIV) or 2-bromo-6-fluoroaniline (I) with 2-methoxy-5-(trifluoromethyl)phenyl isocyanate (V) in refluxing acetonitrile yields the corresponding diaryl ureas (XV) or (XVI), respec-tively. The N-(2-Fluorophenyl)urea derivative (XV) is then condensed with methyl acrylate (II) by means of Pd(OAc)2 and H2S2O7 in AcoH to give the corresponding (E)-cinnamate (XVII), which finally undergoes intramolecular Michael addition in the presence of DBU in refluxing acetone .
Alternatively, intermediate (XI) is obtained by Heck coupling of aryl bromide (XVI) with methyl acrylate (II) in the presence of Pd(MeCn)2Cl2, (o-tol)3P and Et3n in isobutyronitrile at 90-102 °C .

1 Goossen, K., Kuhn, o., Berwe, M., Krueger, J., Militzer, H.-C. (Bayer HealthCare AG). Method for producing dihydroquinazolines. Cn 101863843, DE 10227517, EP 1893587, JP 2008543797, US 2009221822, US 8084604, US 2012130072, US 8372972, Wo 2006133822.
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) 68030 2-bromo-6-fluoroaniline 65896-11-9 C6H5BrFN 详情 详情
(II) 14156 methyl acrylate 96-33-3 C4H6O2 详情 详情
(V) 68033 2-methoxy-5-(trifluoromethyl)phenyl isocyanate 16588-75-3 C9H6F3NO2 详情 详情
(XI) 68037 methyl 2-(8-fluoro-3-(2-methoxy-5-(trifluoromethyl)phenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-4-yl)acetate   C19H16F4N2O4 详情 详情
(XIV) 22296 2-fluorophenylamine; 2-fluoroaniline 348-54-9 C6H6FN 详情 详情
(XV) 68040 1-(2-fluorophenyl)-3-(2-methoxy-5-(trifluoromethyl)phenyl)urea   C15H12F4N2O2 详情 详情
(XVI) 68041 1-(2-bromo-6-fluorophenyl)-3-(2-methoxy-5-(trifluoromethyl)phenyl)urea   C15H11BrF4N2O2 详情 详情
(XVII) 68042 (E)-methyl 3-(3-fluoro-2-(3-(2-methoxy-5-(trifluoromethyl)phenyl)ureido)phenyl)acrylate   C19H16F4N2O4 详情 详情
Extended Information