Sodium hydride → N-isobutyl-N-(5-isopropylpyridin-2-yl)-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

HRID 594161노트

반응식

HRID 594161 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[O:25]1[CH2:30][CH2:29][CH:28]([CH2:31][OH:32])[CH2:27][CH2:26]1.[H-].[Na+]>CN(C)C=O>[CH2:21]([N:11]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=1)[S:8]([C:5]1[CH:6]=[CH:7][C:2]([O:32][CH2:31][CH:28]2[CH2:29][CH2:30][O:25][CH2:26][CH2:27]2)=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH:22]([CH3:24])[CH3:23]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 2773573(Oxan-4-yl)methanolHCID 898760314-fluoro-N-isobutyl-N-(5-isopropylpyridin-2-yl)benzenesulfonamide

생성물 1

HCID 72194555N-isobutyl-N-(5-isopropylpyridin-2-yl)-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide수율 44.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-fluoro-N-isobutyl-N-(5-isopropylpyridin-2-yl)benzenesulfonamide (30 mg, 0.086 mmol) was dissolved in N,N-dimethylformamide (DMF) (3 mL) and to this solution was added (tetrahydro-2H-pyran-4-yl)methanol (12 mg, 0.10 mmol) and sodium hydride (2 mg, 0.10 mmol, 60% wt in mineral oil). The reaction was stirred under nitrogen for 2 hours at room temperature. The reaction was quenched then concentrated in vacuo and the crude product extracted to the organic phase of an aqueous work up between ethyl acetate and water. The organic phase was passed through a hydrophobic frit, concentrated in vacuo and purified by mass directed autoprep (formic acid modifier) to give the title compound (17 mg). LCMS (2 min, formic) Rt 1.41 min, m/z (ES+) 447 (M+H).

후처리

  1. customThe reaction was quenched
  2. concentrationthen concentrated in vacuo
  3. extractionthe crude product extracted to the organic phase of an aqueous work up between ethyl acetate and water
  4. concentrationconcentrated in vacuo
  5. custompurified by mass

출처 및 근거

ORD 기록
ord-2208adb7fdee4a5b8a923081b7d3b575
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242972B2

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