Sodium hydride → HCID 72194693, compound

HRID 594166Notes

Reaction equation

HRID 594166 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]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:20]2[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH:28]([CH3:30])[CH3:29])=[CH:22][N:21]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1.[H-].[Na+]>CS(C)=O>[CH2:31]([N:19]([C:20]1[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH:28]([CH3:30])[CH3:29])=[CH:22][N:21]=1)[S:16]([C:13]1[CH:14]=[CH:15][C:10]([O:8][CH2:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:11][CH:12]=1)(=[O:18])=[O:17])[CH:32]([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2773573(Oxan-4-yl)methanolHCID 89875838HCID 89875838, compound

Product 1

HCID 72194693HCID 72194693, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (tetrahydro-2H-pyran-4-yl)methanol (14.29 mg, 0.123 mmol) and 4-fluoro-N-isobutyl-N-(5-isopropyl-3-methoxypyridin-2-yl)benzenesulfonamide (46.8 mg, 0.123 mmol) in dimethyl sulfoxide (DMSO) (200 μL) stirred in air at room temperature was added sodium hydride (4.92 mg, 0.123 mmol, 60% wt in mineral oil). The reaction mixture was stirred for 4 days then carefully quenched with isopropanol (1 mL) and evaporated in vacuo. The crude sample was purified by mass directed autoprep (formic acid modifier) to give the title product, 42.9 mg. LCMS (2 min, formic) Rt 1.36 min, m/z (ES+) 477 (M+H).

Workup

  1. customthen carefully quenched with isopropanol (1 mL)
  2. customevaporated in vacuo
  3. customThe crude sample was purified by mass

Sources & evidence

ORD record
ord-dd12f00cf6f14c8aab4aaca49e1f0e53
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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