Sodium hydride → HCID 72189588, 화합물

HRID 1487049노트

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HRID 1487049 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]1[CH:18]=[CH:17][C:16](F)=[CH:15][CH:14]=1)(=[O:12])=[O:11].[F:24][C:25]([F:36])([F:35])[CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][OH:34])[CH2:29][CH2:28]1.[H-].[Na+]>CS(C)=O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([O:34][CH2:33][CH:30]2[CH2:31][CH2:32][N:27]([CH2:26][C:25]([F:24])([F:35])[F:36])[CH2:28][CH2:29]2)=[CH:17][CH:18]=1)(=[O:12])=[O:11]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 52274441[1-(2,2,2-Trifluoroethyl)piperidin-4-yl]methanolHCID 89479332HCID 89479332, 화합물

생성물 1

HCID 72189588HCID 72189588, 화합물

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

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온도
20 °C

실험 절차

To a solution of N-(2,4-dimethylphenyl)-4-fluoro-N-isobutylbenzenesulfonamide (25 mg, 0.075 mmol) and (1-(2,2,2-trifluoroethyl)piperidin-4-yl)methanol (14.70 mg, 0.075 mmol) in dimethyl sulfoxide (DMSO) (0.5 mL) stirred in air at 20° C., was added sodium hydride (approximately 2.98 mg, 0.075 mmol, 60% dispersed in oil) in one charge. The reaction mixture was stirred at 20° C. for 16 hours. The reaction was carefully quenched with methanol (0.5 mL) and water (0.5 mL). The solvent was concentrated in vacuo (Biotage V10) to give the crude product in DMSO (0.5 mL). The residue was taken up in additional DMSO (0.5 mL) and methanol (1 mL) then purified by mass directed autoprep (formic acid modifier). The appropriate fractions were evaporated under a stream of nitrogen to give the required product, 11.5 mg. LCMS [LCMS1] Rt 1.51 min, m/z (ES+) 513 (M+H).

후처리

  1. additioncharge
  2. customThe reaction was carefully quenched with methanol (0.5 mL) and water (0.5 mL)
  3. concentrationThe solvent was concentrated in vacuo (Biotage V10)
  4. customto give the crude product in DMSO (0.5 mL)
  5. custommethanol (1 mL) then purified by mass
  6. customThe appropriate fractions were evaporated under a stream of nitrogen

출처 및 근거

ORD 기록
ord-55d549140d3140a2980348d56ed3bfe7
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428452B2

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