Aniline → 5-(6-Phenylcarbamoyl-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide

HRID 2264612ノート

反応式

HRID 2264612 の反応式
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[N:27]=[CH:26][N:25]=[C:24]([C:28](O)=[O:29])[CH:23]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1.C(OP(C#N)(=O)OCC)C.[NH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CN(C=O)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:23]=[C:24]([C:28](=[O:29])[NH:43][C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[N:25]=[CH:26][N:27]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1

参加物

7

反応物 3

HCID 6115AnilineHCID 76257Diethyl cyanophosphonate2 回HCID 59596375HCID 59596375、化合物

生成物 1

HCID 595963495-(6-Phenylcarbamoyl-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To an ice-cooled solution of 400 mg (0.90 mMol) 6-[1-(3-trifluoromethyl-phenylcarbamoyl)-2,3-dihydro-1H-indol-5-yloxy]-pyrimidine-4-carboxylic acid in 4 ml DMF, 402 μl (2.7 mMol) diethyl-cyanophosphonate and 248 μl (2.7 mMol) aniline are added. After stirring the solution for 3 h at rt, another 402 μl diethyl-cyanophosphonate are added and stirring continued for 16 h. Then the mixture is diluted with EtOAc and sat. NaHCO3, the aqueous layer separeted off and extracted twice with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and partially concentrated until crystals are formed. These are filtered and washed with EtOAC/DIPE, yielding the title compound: m.p.: 227-229° C.; MS: [M−1]=518; HPLC: AtRet=17.2.

後処理

  1. additionare added
  2. stirringstirring
  3. waitcontinued for 16 h
  4. extractionextracted twice with EtOAc
  5. washThe organic phases are washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationpartially concentrated until crystals
  8. customare formed
  9. filtrationThese are filtered
  10. washwashed with EtOAC/DIPE

出典と根拠

ORDレコード
ord-fa72f1fdde634e7ab994933aa8a8f49d
出典データセット
uspto-grants-2010_12
特許番号
US07855215B2

反応ノート

読み込み中…