Sodium hydride → HCID 72189588、化合物

HRID 1487049ノート

反応式

HRID 1487049 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 72189588HCID 72189588、化合物

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

反応条件

温度
20 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-55d549140d3140a2980348d56ed3bfe7
出典データセット
uspto-grants-2016_08
特許番号
US09428452B2

反応ノート

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