Acetonitrile → (S)-1-(2-(5-((Dimethylamino)methyl)isoxazol-3-yl)pyrrolidin-1-yl)-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone

HRID 710038노트

반응식

HRID 710038 반응식
CS(O[CH2:6][C:7]1[O:11][N:10]=[C:9]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17](=[O:32])[C:18]([F:31])([F:30])[C:19]2([OH:29])[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:21]([CH3:28])([CH3:27])[CH2:20]2)[CH:8]=1)(=O)=O.C1COCC1.[CH3:38]COC(C)=O.C[C:45]#[N:46]>>[CH3:38][N:46]([CH2:6][C:7]1[O:11][N:10]=[C:9]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17](=[O:32])[C:18]([F:30])([F:31])[C:19]2([OH:29])[CH2:24][C:23]([CH3:25])([CH3:26])[CH2:22][C:21]([CH3:28])([CH3:27])[CH2:20]2)[CH:8]=1)[CH3:45]

참가 물질

5

반응물 4

HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 86706749(S)-(3-(1-(2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)acetyl)pyrrolidin-2-yl)isoxazol-5-yl)methyl methanesulfonate

생성물 1

HCID 73672156(S)-1-(2-(5-((Dimethylamino)methyl)isoxazol-3-yl)pyrrolidin-1-yl)-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone

실험 절차

The compound (160 mg) obtained in Example 3-(5) was dissolved in MeCN and after adding a THF solution of dimethyllamine (2 M, 250 μL), the mixture was stirred at room temperature for 3 hours. To the reaction mixture, AcOEt (50 ml) and a saturated aqueous solution of NaCO3 (50 ml) were added to separate the organic layer. The resulting organic layer was washed with brine (50 ml), dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (83 mg, colorless amorphous.)

후처리

  1. customto separate the organic layer
  2. washThe resulting organic layer was washed with brine (50 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product, which
  7. customwas further purified by silica gel chromatography (AcOEt/hexane)

출처 및 근거

ORD 기록
ord-6bcebc64d7a64470aa40ec0ac8e1962a
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181229B2

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