Benzenesulfonyl chloride → HCID 9809494, compound

HRID 1017470Notes

Reaction equation

HRID 1017470 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.[C:36]1([S:42](Cl)(=[O:44])=[O:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>ClCCl.C(N(C(C)C)C(C)C)C>[C:36]1([S:42]([NH:1][C:2]2[N:7]=[CH:6][C:5]([N:8]([CH3:28])[C:9](=[O:27])[C:10]([C:13]3[CH:14]=[C:15]([C:23]([F:26])([F:24])[F:25])[CH:16]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:18]=3)([CH3:12])[CH3:11])=[C:4]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[CH:3]=2)(=[O:44])=[O:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 9913704HCID 9913704, compound

Product 1

HCID 9809494HCID 9809494, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

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 in 4 ml dichloromethane and 85 μl N-ethyldiisopropylamine were added 56 μl (0.436 mmol) benzenesulfonyl chloride and the mixture was stirred over night at room temperature. The reaction mixture was washed twice with saturated aqueous sodium hydrogencarbonate solution and dried (magnesium sulfate). Chromatography of the residue afforded 26 mg (28%) of the title compound as a white foam.

Workup

  1. washThe reaction mixture was washed twice with saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialdried (magnesium sulfate)

Sources & evidence

ORD record
ord-16e12c1846c94b7687db2aad05f64d6f
Source dataset
uspto-grants-2002_11
Patent number
US06479483B2

Reaction notes

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