4-Chloro-6-(trifluoromethyl)pyrimidine → (S)-tert-butyl 2-(2-fluoro-4-(1-(6-(trifluoromethyl)pyrimidin-4-yl)-1H-pyrazole-4-carboxamido)phenyl)morpholine-4-carboxylate

HRID 571886ノート

反応式

HRID 571886 の反応式
[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[CH:12]=[N:13][NH:14][CH:15]=2)=[O:10])[CH:5]=[CH:4][C:3]=1[C@@H:16]1[O:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1.Cl[C:30]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[N:33]=[CH:32][N:31]=1>CS(C)=O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]([C:30]3[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[N:33]=[CH:32][N:31]=3)[CH:15]=2)=[O:10])[CH:5]=[CH:4][C:3]=1[C@@H:16]1[O:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1

参加物

4

反応物 2

HCID 115428814-Chloro-6-(trifluoromethyl)pyrimidineHCID 71087137(S)-tert-butyl 2-(2-fluoro-4-(1H-pyrazole-4-carboxamido)phenyl)morpholine-4-carboxylate

生成物 1

HCID 71087182(S)-tert-butyl 2-(2-fluoro-4-(1-(6-(trifluoromethyl)pyrimidin-4-yl)-1H-pyrazole-4-carboxamido)phenyl)morpholine-4-carboxylate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

Under N2, (S)-tert-butyl 2-(2-fluoro-4-(1H-pyrazole-4-carboxamido)phenyl)morpholine-4-carboxylate (60 mg, 154 μmol, Eq: 1.00), 4-chloro-6-(trifluoromethyl)-pyrimidine (CAS 37552-81-1) (28 mg, 154 μmol, Eq: 1.00) and were combined in DMSO (2 ml). The orange solution was stirred at 120° C. over 1 hour. Control with TLC: the reaction was finished. At RT, the RM was partitioned between water and EtOAc; extracted; the organic layer was washed with water and brine; dried over MgSO4; filtered; concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10 g, 15% to 60% EtOAc in heptane). Yellow solid (41 mg). MS: 535.7 ([M−H]−)

後処理

  1. customAt RT, the RM was partitioned between water and EtOAc
  2. extractionextracted
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (silica gel, 10 g, 15% to 60% EtOAc in heptane)

出典と根拠

ORDレコード
ord-f134b766870b431ebb437ef8aba72f6b
出典データセット
uspto-grants-2015_05
特許番号
US09029370B2

反応ノート

読み込み中…