Sodium hydride → HCID 72189588, compound

HRID 1487049Notes

Reaction equation

HRID 1487049 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]1[CH:18]=[CH:17][C:16](F)=[CH:15][CH:14]=1)(=[O:12])=[O:11].[F:24][C:25]([F:36])([F:35])[CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][OH:34])[CH2:29][CH2:28]1.[H-].[Na+]>CS(C)=O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([O:34][CH2:33][CH:30]2[CH2:31][CH2:32][N:27]([CH2:26][C:25]([F:24])([F:35])[F:36])[CH2:28][CH2:29]2)=[CH:17][CH:18]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 52274441[1-(2,2,2-Trifluoroethyl)piperidin-4-yl]methanolHCID 89479332HCID 89479332, compound

Product 1

HCID 72189588HCID 72189588, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of N-(2,4-dimethylphenyl)-4-fluoro-N-isobutylbenzenesulfonamide (25 mg, 0.075 mmol) and (1-(2,2,2-trifluoroethyl)piperidin-4-yl)methanol (14.70 mg, 0.075 mmol) in dimethyl sulfoxide (DMSO) (0.5 mL) stirred in air at 20° C., was added sodium hydride (approximately 2.98 mg, 0.075 mmol, 60% dispersed in oil) in one charge. The reaction mixture was stirred at 20° C. for 16 hours. The reaction was carefully quenched with methanol (0.5 mL) and water (0.5 mL). The solvent was concentrated in vacuo (Biotage V10) to give the crude product in DMSO (0.5 mL). The residue was taken up in additional DMSO (0.5 mL) and methanol (1 mL) then purified by mass directed autoprep (formic acid modifier). The appropriate fractions were evaporated under a stream of nitrogen to give the required product, 11.5 mg. LCMS [LCMS1] Rt 1.51 min, m/z (ES+) 513 (M+H).

Workup

  1. additioncharge
  2. customThe reaction was carefully quenched with methanol (0.5 mL) and water (0.5 mL)
  3. concentrationThe solvent was concentrated in vacuo (Biotage V10)
  4. customto give the crude product in DMSO (0.5 mL)
  5. custommethanol (1 mL) then purified by mass
  6. customThe appropriate fractions were evaporated under a stream of nitrogen

Sources & evidence

ORD record
ord-55d549140d3140a2980348d56ed3bfe7
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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