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【结 构 式】

【分子编号】61850

【品名】N-[2-(1-ethoxyvinyl)phenyl]-N-methyl-2-(4-morpholinyl)acetamide

【CA登记号】

【 分 子 式 】C17H24N2O3

【 分 子 量 】304.38924

【元素组成】C 67.08% H 7.95% N 9.2% O 15.77%

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:(XV)

2-Bromoaniline (VIII) is acylated by bromoacetyl chloride (IX) in pyridine to produce the corresponding bromoacetanilide (X). Subsequent displacement of the aliphatic bromide of (X) with morpholine (XI) furnishes the morpholinoacetanilide (XII). Alkylation at the amide N of (XII) with iodomethane and NaH leads to the N-methyl amide (XIII). Stille coupling of aryl bromide (XIII) with tributyl (1-ethoxyvinyl)tin (XIV) yields the enol ether (XV). Bromination of enol ether (XV) with N-bromosuccinimide in moist THF produces the bromo acetophenone (XVI), which is further reacted with NaN3 to give the azido ketone (XVII). The target amino oxazole compound is finally obtained by condensation of azido ketone (XVII) with isothiocyanate (VII) in the presence of PPh3 in hot dioxane.

1 Liu, C.; Leftheris, K.; Pitts, W.J.; Iwanowicz, E.J.; Dhar, T.G.M.; Gu, H.H. (Bristol-Myers Squibb Co.); Cpds. derived from an amine nucleus that are inhibitors of IMPDH enzyme. EP 1126843; US 6399773; WO 0025780 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 61697 3-methoxy-4-(1,3-oxazol-5-yl)phenyl isothiocyanate; 5-(4-isothiocyanato-2-methoxyphenyl)-1,3-oxazole C11H8N2O2S 详情 详情
(VIII) 27739 2-bromoaniline 615-36-1 C6H6BrN 详情 详情
(IX) 27903 2-Bromoacetyl chloride 22118-09-8 C2H2BrClO 详情 详情
(X) 61698 2-bromo-N-(2-bromophenyl)acetamide C8H7Br2NO 详情 详情
(XI) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(XII) 61699 N-(2-bromophenyl)-2-(4-morpholinyl)acetamide C12H15BrN2O2 详情 详情
(XIII) 61700 N-(2-bromophenyl)-N-methyl-2-(4-morpholinyl)acetamide C13H17BrN2O2 详情 详情
(XIV) 19760 ethyl 1-(tributylstannyl)vinyl ether; tributyl(1-ethoxyvinyl)stannane 97674-02-7 C16H34OSn 详情 详情
(XV) 61850 N-[2-(1-ethoxyvinyl)phenyl]-N-methyl-2-(4-morpholinyl)acetamide C17H24N2O3 详情 详情
(XVI) 61851 N-[2-(2-bromoacetyl)phenyl]-N-methyl-2-(4-morpholinyl)acetamide C15H19BrN2O3 详情 详情
(XVII) 61852 N-[2-(2-azidoacetyl)phenyl]-N-methyl-2-(4-morpholinyl)acetamide C15H19N5O3 详情 详情
Extended Information