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

HRID 594155Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of N-(3,5-dimethylpyridin-2-yl)-4-fluoro-N-isobutylbenzenesulfonamide (53.7 mg, 0.160 mmol) and (tetrahydro-2H-pyran-4-yl)methanol (18.54 mg, 0.160 mmol) in dimethyl sulfoxide (DMSO) (1 mL) stirred at room temperature, was added sodium hydride (4.79 mg, 0.160 mmol, 60% wt in mineral oil). The reaction mixture was stirred at 20° C. for 2 hour, then left to stand overnight. Additional sodium hydride (4.79 mg, 0.160 mmol, 60% wt in mineral oil) was added and the reaction stirred for a further 2 hours. The reaction was quenched with methanol (0.5 mL) and water (0.5 mL), then concentrated in vacuo. The crude was purified by mass directed autoprep (formic acid modifier) to give the title compound (31.3 mg). LCMS (2 min, formic) Rt 1.38 min, m/z (ES+) 433 (M+H).

Workup

waitleft
waitto stand overnight
stirringthe reaction stirred for a further 2 hours
customThe reaction was quenched with methanol (0.5 mL) and water (0.5 mL)
concentrationconcentrated in vacuo
customThe crude was purified by mass

Sources & evidence

ORD record: ord-2adeb4af54a84053a26daec5a9fef42f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242972B2

Reaction notes

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