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

HRID 594168Notes

Reaction equation

[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)[CH2:20][CH:21]2[CH2:24][O:23][CH2:22]2)(=[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]([CH2:20][CH:21]2[CH2:22][O:23][CH2:24]2)[S:16]([C:13]2[CH:14]=[CH:15][C:10]([O:8][CH2:7][CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:11][CH:12]=2)(=[O:18])=[O:17])=[N:26][CH:27]=1)([CH3:33])[CH3:32]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of (tetrahydro-2H-pyran-4-yl)methanol (20.08 mg, 0.173 mmol) and 4-fluoro-N-(5-isopropylpyridin-2-yl)-N-(oxetan-3-ylmethyl)benzenesulfonamide (63 mg, 0.173 mmol) in dimethyl sulfoxide (DMSO) (1 mL) stirred in air at room temperature was added sodium hydride (6.91 mg, 0.173 mmol, 60% wt in mineral oil). The reaction mixture was stirred at 20° C. for 2 hours. The reaction mixture was carefully quenched with methanol (2 mL) and water (2 mL), then solvents evaporated in vacuo. The crude product was purified by flash silica (Si) (25% ethyl acetate-cyclohexane gradient) to give the title product (63.2 mg). LCMS (2 min, High pH) Rt 1.23 min, m/z (ES+) 461 (M+H).

Workup

customThe reaction mixture was carefully quenched with methanol (2 mL) and water (2 mL)
customsolvents evaporated in vacuo
customThe crude product was purified by flash silica (Si) (25% ethyl acetate-cyclohexane gradient)

Sources & evidence

ORD record: ord-c0cb1c1dd2e74dd6b19da592c76de1d7
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242972B2

Reaction notes

Loading…