Water → HCID 18403339, compound

HRID 379405Notes

Reaction equation

HRID 379405 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:28])[C:9](=[O:27])[C:10]([C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=2)([CH3:12])[CH3:11])=[C:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[CH:3]=1.[H-].[Na+].C1(S(Cl)(=O)=O)C=CC=CC=1.O>CN(C)C=O>[F:22][C:19]([F:20])([F:21])[C:17]1[CH:18]=[C:13]([C:10]([CH3:12])([CH3:11])[C:9]([N:8]([C:5]2[CH:6]=[N:7][C:2]([N:1]=[CH:5][N:8]([CH3:28])[CH3:9])=[CH:3][C:4]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[CH3:28])=[O:27])[CH:14]=[C:15]([C:23]([F:26])([F:24])[F:25])[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 9913704HCID 9913704, compound

Product 1

HCID 18403339HCID 18403339, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg (0.2 mmol) N-(6-amino-4-o-tolyl-pyridin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide (Example 73) in 4 ml N,N-dimethylformamide was added at 0° C. 11 mg (0.252 mmol) sodium hydride as a 60% dispersion in oil and the mixture was stirred for 30 min without cooling. Then 28 il (0.218 mmol) benzenesulfonyl chloride were added at 0° C. and the solution was stirred over night at room temperature. The reaction mixture was added to water and extracted with ethyl acetate (3×10 ml). The combined extracts were washed with water (3×20 ml), brine (20 ml), dried (magnesium sulfate) and evaporated. Chromatography of the residue afforded 51 mg (46%) of the title compound as a white foam.

Workup

  1. temperaturewithout cooling
  2. extractionextracted with ethyl acetate (3×10 ml)
  3. washThe combined extracts were washed with water (3×20 ml), brine (20 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-f443297c02b249db81f93ee28f4a1172
Source dataset
uspto-grants-2001_10
Patent number
US06297375B1

Reaction notes

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