Methanesulfonyl chloride → HCID 9894350, compound

HRID 379406Notes

Reaction equation

HRID 379406 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.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>N1C=CC=CC=1>[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]([NH:1][S:37]([CH3:36])(=[O:39])=[O:38])=[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

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 9913704HCID 9913704, compound

Product 1

HCID 9894350HCID 9894350, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 i (Example 73) in 2 ml pyridine were added 27 μl (0.35 mmol) methanesulfonyl chloride and the mixture was stirred over night at room temperature. After evaporation of the solvent the residue was dissolved in ethyl acetate, washed twice with saturated aqueous sodium hydrogencarbonate solution, brine and dried (magnesium sulfate). Chromatography of the residue afforded 24 mg (42%) of the title compound as a white foam.

Workup

  1. customAfter evaporation of the solvent the residue
  2. dissolutionwas dissolved in ethyl acetate
  3. washwashed twice with saturated aqueous sodium hydrogencarbonate solution, brine
  4. dry with materialdried (magnesium sulfate)

Sources & evidence

ORD record
ord-fb82086eef4a4e548f17860357f2e850
Source dataset
uspto-grants-2001_10
Patent number
US06297375B1

Reaction notes

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