【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% |
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 |