Sodium hydride → 2-chloro-N-(3,5-dimethylpyridin-2-yl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

HRID 594152ノート

反応式

HRID 594152 の反応式
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[Cl:9][C:10]1[CH:15]=[C:14](F)[CH:13]=[CH:12][C:11]=1[S:17]([N:20]([C:25]1[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][N:26]=1)[CH2:21][CH:22]([CH3:24])[CH3:23])(=[O:19])=[O:18].[H-].[Na+]>CS(C)=O>[Cl:9][C:10]1[CH:15]=[C:14]([O:1][CH2:2][CH:3]2[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH:13]=[CH:12][C:11]=1[S:17]([N:20]([C:25]1[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][N:26]=1)[CH2:21][CH:22]([CH3:23])[CH3:24])(=[O:19])=[O:18]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 2773573(Oxan-4-yl)methanolHCID 898760522-chloro-N-(3,5-dimethylpyridin-2-yl)-4-fluoro-N-isobutylbenzenesulfonamide

生成物 1

HCID 721942782-chloro-N-(3,5-dimethylpyridin-2-yl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide収率 48.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a stirred solution of 4-(hydroxylmethyl)tetrahydro-2H-pyran (2.63 mg, 0.023 mmol) and 2-chloro-N-(3,5-dimethylpyridin-2-yl)-4-fluoro-N-isobutylbenzenesulfonamide (8.4 mg, 0.023 mmol) in dimethyl sulfoxide (200 μL) at room temperature was added sodium hydride (60% wt in mineral oil) (0.906 mg, 0.023 mmol) and the reaction stirred for 2 hours. The reaction was quenched with methanol (2 mL) and water (2 mL), then the solvents evaporated in vacuo. The crude product was purified by flash silica (Si) chromatography (25% ethyl acetate-cyclohexane gradient) to give the title compound (5.2 mg). LCMS (2 min, High pH) Rt 1.48 min, m/z (ES+) 468 (M+H).

後処理

  1. customThe reaction was quenched with methanol (2 mL) and water (2 mL)
  2. customthe solvents evaporated in vacuo
  3. customThe crude product was purified by flash silica (Si) chromatography (25% ethyl acetate-cyclohexane gradient)

出典と根拠

ORDレコード
ord-623da59365e54c6c893e14d6e6078a64
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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