Diisopropylethylamine → 1-[4-(1-Benzhydryl-azetidin-3-yl)-piperazin-1-yl]-2,2,2-trifluoro-ethanone

HRID 1961370

반응식

HRID 1961370 반응식
[F:1][C:2]([F:12])([F:11])[C:3]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].CS(O[CH:18]1[CH2:21][N:20]([CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19]1)(=O)=O.CCN(C(C)C)C(C)C>CC#N>[CH:22]([N:20]1[CH2:21][CH:18]([N:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[C:2]([F:1])([F:11])[F:12])[CH2:6][CH2:7]2)[CH2:19]1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 7172020Trifluoroacetylpiperazine

생성물 1

HCID 596259751-[4-(1-Benzhydryl-azetidin-3-yl)-piperazin-1-yl]-2,2,2-trifluoro-ethanone

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 2,2,2-trifluoro-1-piperazin-1-yl-ethanone (6 g, 32.94 mmol) and 1-benzhydrylazetidin-3-yl methanesulfonate (12.5 g, 39.38 mmol) in CH3CN (60 mL) was added DIPEA (12 mL, 68.89 mmol) at room temperature. The resulting mixture was refluxed for 2 h. The solvent was removed by evaporation and the residue was partitioned between CH2Cl2 and aq NaHCO3. The organic layer was washed with aq NaHCO3 (2×) and then extracted with 1N HCl (2×). The aqueous layer was cooled and then the pH adjusted with 1N NaOH until basic (pH=10). The resulting mixture was extracted with CH2Cl2 (2×). The organic layer was dried over MgSO4 and concentrated. The title compound was purified by reverse phase chromatography. MS m/z (M+H+) 404.2.

후처리

  1. temperatureThe resulting mixture was refluxed for 2 h
  2. customThe solvent was removed by evaporation
  3. customthe residue was partitioned between CH2Cl2 and aq NaHCO3
  4. washThe organic layer was washed with aq NaHCO3 (2×)
  5. extractionextracted with 1N HCl (2×)
  6. temperatureThe aqueous layer was cooled
  7. extractionThe resulting mixture was extracted with CH2Cl2 (2×)
  8. dry with materialThe organic layer was dried over MgSO4
  9. concentrationconcentrated
  10. customThe title compound was purified by reverse phase chromatography

출처 및 근거

ORD 기록
ord-893899b95da4431baf8e5b74045dabaa
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415341B2

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