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

Temperature

20 °C

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).

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

ORD record

ord-8785bb45fb514abf87f805e99869b103

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242972B2