Sodium hydride → N-(5-isopropylpyridin-2-yl)-N-(3-methylbutan-2-yl)-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

HRID 594165ノート

反応式

HRID 594165 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.F[C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][N:26]=2)[CH:20]([CH:22]([CH3:24])[CH3:23])[CH3:21])(=[O:18])=[O:17])=[CH:12][CH:11]=1.[H-].[Na+]>CS(C)=O>[CH:31]([C:28]1[CH:29]=[CH:30][C:25]([N:19]([CH:20]([CH:22]([CH3:24])[CH3:23])[CH3:21])[S:16]([C:13]2[CH:12]=[CH:11][C:10]([O:8][CH2:7][CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:15][CH:14]=2)(=[O:17])=[O:18])=[N:26][CH:27]=1)([CH3:33])[CH3:32]

参加物

5

反応物 3

HCID 24758Sodium hydride2 回HCID 2773573(Oxan-4-yl)methanol2 回HCID 898762524-fluoro-N-(5-isopropylpyridin-2-yl)-N-(3-methylbutan-2-yl)benzenesulfonamide

生成物 1

HCID 72194692N-(5-isopropylpyridin-2-yl)-N-(3-methylbutan-2-yl)-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide収率 78.9%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
20 °C

実験手順

To a solution of (tetrahydro-2H-pyran-4-yl)methanol (10.20 mg, 0.088 mmol) and 4-fluoro-N-(5-isopropylpyridin-2-yl)-N-(3-methylbutan-2-yl)benzenesulfonamide (32 mg, 0.088 mmol) in dimethyl sulfoxide (DMSO) (1 mL) stirred in air at room temperature was added sodium hydride (3.51 mg, 0.088 mmol, 60% wt in mineral oil). The reaction mixture was stirred at 20° C. for 2 hours. Additional (tetrahydro-2H-pyran-4-yl)methanol (10.20 mg, 0.088 mmol) and sodium hydride (3.51 mg, 0.088 mmol, 60% wt in mineral oil) were added and the reaction mixture stirred overnight. The reaction was carefully quenched with isopropanol (1 mL) and water (1 mL). The solvent was evaporated in vacuo and the residue partitioned between water (5 mL) and dichloromethane (2×5 mL), then separated using a hydrophobic frit. The solvent was removed in vacuo and the crude was purified by mass directed autoprep (formic acid modifier) to give the title product (32 mg). LCMS (2 min, formic) Rt 1.41 min, m/z (ES+) 461 (M+H).

後処理

  1. stirringthe reaction mixture stirred overnight
  2. customThe reaction was carefully quenched with isopropanol (1 mL) and water (1 mL)
  3. customThe solvent was evaporated in vacuo
  4. customthe residue partitioned between water (5 mL) and dichloromethane (2×5 mL)
  5. customseparated
  6. customThe solvent was removed in vacuo
  7. customthe crude was purified by mass

出典と根拠

ORDレコード
ord-8785bb45fb514abf87f805e99869b103
出典データセット
uspto-grants-2016_01
特許番号
US09242972B2

反応ノート

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