HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium hydride → N-(3,5-dimethylpyridin-2-yl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

HRID 594155
Notes
Print preview

Reaction equation

HRID 594155 reaction equation
[CH3:1][C:2]1[C:3]([N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]2[CH:18]=[CH:17][C:16](F)=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[O:24]1[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][CH2:25]1.[H-].[Na+]>CS(C)=O>[CH3:1][C:2]1[C:3]([N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]2[CH:18]=[CH:17][C:16]([O:31][CH2:30][CH:27]3[CH2:28][CH2:29][O:24][CH2:25][CH2:26]3)=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 2773573(Oxan-4-yl)methanolHCID 89876058N-(3,5-dimethylpyridin-2-yl)-4-fluoro-N-isobutylbenzenesulfonamide

Product 1

HCID 72194282N-(3,5-dimethylpyridin-2-yl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamideYield 45.2%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
20 °C

Procedure

To a solution of N-(3,5-dimethylpyridin-2-yl)-4-fluoro-N-isobutylbenzenesulfonamide (53.7 mg, 0.160 mmol) and (tetrahydro-2H-pyran-4-yl)methanol (18.54 mg, 0.160 mmol) in dimethyl sulfoxide (DMSO) (1 mL) stirred at room temperature, was added sodium hydride (4.79 mg, 0.160 mmol, 60% wt in mineral oil). The reaction mixture was stirred at 20° C. for 2 hour, then left to stand overnight. Additional sodium hydride (4.79 mg, 0.160 mmol, 60% wt in mineral oil) was added and the reaction stirred for a further 2 hours. The reaction was quenched with methanol (0.5 mL) and water (0.5 mL), then concentrated in vacuo. The crude was purified by mass directed autoprep (formic acid modifier) to give the title compound (31.3 mg). LCMS (2 min, formic) Rt 1.38 min, m/z (ES+) 433 (M+H).

Workup

  1. waitleft
  2. waitto stand overnight
  3. stirringthe reaction stirred for a further 2 hours
  4. customThe reaction was quenched with methanol (0.5 mL) and water (0.5 mL)
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by mass

Sources & evidence

ORD record
ord-2adeb4af54a84053a26daec5a9fef42f
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242972B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes