Dichloromethane → N-{6-[1-(Dimethylsulfamoyl)piperidin-4-yl]-5-methylpyridin-3-yl}-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748686Notes

Reaction equation

HRID 1748686 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:14])[S:10](Cl)(=[O:12])=[O:11].[CH3:15][C:16]1[N:20]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][N:22]=2)[N:19]=[CH:18][C:17]=1[C:31]([NH:33][C:34]1[CH:35]=[N:36][C:37]([CH:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)=[C:38]([CH3:40])[CH:39]=1)=[O:32].ClCCl>O>[CH3:8][N:9]([CH3:14])[S:10]([N:44]1[CH2:43][CH2:42][CH:41]([C:37]2[N:36]=[CH:35][C:34]([NH:33][C:31]([C:17]3[CH:18]=[N:19][N:20]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][N:22]=4)[C:16]=3[CH3:15])=[O:32])=[CH:39][C:38]=2[CH3:40])[CH2:46][CH2:45]1)(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471Triethylamine2×HCID 83372Dimethylsulphamoyl chloride2×HCID 866925445-Methyl-N-[5-methyl-6-(piperidin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Product 1

HCID 86692636N-{6-[1-(Dimethylsulfamoyl)piperidin-4-yl]-5-methylpyridin-3-yl}-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (73 μl) and dimethylsulfamoyl chloride (56 μl) were added to a mixture of 5-methyl-N-[5-methyl-6-(piperidin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (222 mg) described in Reference Example 171 and dichloromethane (10 ml), stirred at room temperature for 6.5 hours, triethylamine (146 μl) and dimethylsulfamoyl chloride (56 μl) were added and stirred at room temperature for 7.5 hours. Water was added to the reaction solution, extracted with chloroform, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The precipitated solid was washed with ethyl acetate and ethanol to give the titled compound (122 mg) as a white solid.

Workup

  1. stirringstirred at room temperature for 7.5 hours
  2. extractionextracted with chloroform
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. washThe precipitated solid was washed with ethyl acetate and ethanol

Sources & evidence

ORD record
ord-6a5276de0c8b4ae0904068fa150a32d3
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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