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

HRID 1850234노트

반응식

HRID 1850234 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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]

출처 및 근거

ORD 기록
ord-15b5b44e3a10433ebe89b9dc13ebf042
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957068B2

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