Diisopropylethylamine → (S)-4-isopropyl-3-(2-(((S)-1-(4-(pyrimidin-5-yloxy)phenyl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one

HRID 1850234ノート

反応式

HRID 1850234 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]2=[O:16])[CH:5]=[CH:4][N:3]=1.[N:17]1[CH:22]=[C:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([C@@H:30]([NH2:32])[CH3:31])=[CH:26][CH:25]=2)[CH:20]=[N:19][CH:18]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH:13]([C@H:12]1[CH2:11][O:10][C:9](=[O:16])[N:8]1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:32][C@H:30]([C:27]2[CH:26]=[CH:25][C:24]([O:23][C:21]3[CH:20]=[N:19][CH:18]=[N:17][CH:22]=3)=[CH:29][CH:28]=2)[CH3:31])[N:7]=1)([CH3:15])[CH3:14]

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 86730167(S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-oneHCID 86730203(S)-1-(4-(pyrimidin-5-yloxy)phenyl)ethanamine

生成物 1

HCID 86730288(S)-4-isopropyl-3-(2-(((S)-1-(4-(pyrimidin-5-yloxy)phenyl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one収率 9.9%

試薬・触媒・溶媒 3

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
110 °C

実験手順

To the solution of (S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (43 mg, 0.169 mmol) in NMP (0.7 mL) was added (S)-1-(4-(pyrimidin-5-yloxy)phenyl)ethanamine (41 mg, 0.169 mmol) and DIEA (88 μL, 0.507 mmol). The brown reaction mixture was stirred at 110° C. for 2 days. The reaction mixture was diluted with ethyl acetate and aqueous sodium bicarbonate solution. The separated organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine. The organic phase was dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by reverse phase column chromatography [C-18] to provide (S)-4-isopropyl-3-(2-(((S)-1-(4-(pyrimidin-5-yloxy)phenyl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one (7 mg) as its trifluoroacetic acid salt.

後処理

  1. washThe separated organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered off
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by reverse phase column chromatography [C-18]

出典と根拠

ORDレコード
ord-15b5b44e3a10433ebe89b9dc13ebf042
出典データセット
uspto-grants-2015_02
特許番号
US08957068B2

反応ノート

読み込み中…