Sodium hydride → N-isobutyl-N-(5-isopropylpyridin-2-yl)-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide
Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[O:25]1[CH2:30][CH2:29][CH:28]([CH2:31][OH:32])[CH2:27][CH2:26]1.[H-].[Na+]>CN(C)C=O>[CH2:21]([N:11]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=1)[S:8]([C:5]1[CH:6]=[CH:7][C:2]([O:32][CH2:31][CH:28]2[CH2:29][CH2:30][O:25][CH2:26][CH2:27]2)=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH:22]([CH3:24])[CH3:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4-fluoro-N-isobutyl-N-(5-isopropylpyridin-2-yl)benzenesulfonamide (30 mg, 0.086 mmol) was dissolved in N,N-dimethylformamide (DMF) (3 mL) and to this solution was added (tetrahydro-2H-pyran-4-yl)methanol (12 mg, 0.10 mmol) and sodium hydride (2 mg, 0.10 mmol, 60% wt in mineral oil). The reaction was stirred under nitrogen for 2 hours at room temperature. The reaction was quenched then concentrated in vacuo and the crude product extracted to the organic phase of an aqueous work up between ethyl acetate and water. The organic phase was passed through a hydrophobic frit, concentrated in vacuo and purified by mass directed autoprep (formic acid modifier) to give the title compound (17 mg). LCMS (2 min, formic) Rt 1.41 min, m/z (ES+) 447 (M+H).
Workup
- customThe reaction was quenched
- concentrationthen concentrated in vacuo
- extractionthe crude product extracted to the organic phase of an aqueous work up between ethyl acetate and water
- concentrationconcentrated in vacuo
- custompurified by mass
Sources & evidence
- ORD record
- ord-2208adb7fdee4a5b8a923081b7d3b575
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242972B2
Reaction notes
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