Water → HCID 86692624, compound

HRID 1748677Notes

Reaction equation

HRID 1748677 reaction equation
[CH:1]([S:4](Cl)(=[O:6])=[O:5])([CH3:3])[CH3:2].[C:8]([C:10]1([C:16]2[N:21]=[CH:20][C:19]([NH:22][C:23]([C:25]3[CH:26]=[N:27][N:28]([C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][N:32]=4)[C:29]=3[CH3:30])=[O:24])=[CH:18][CH:17]=2)[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)#[N:9].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:8]([C:10]1([C:16]2[N:21]=[CH:20][C:19]([NH:22][C:23]([C:25]3[CH:26]=[N:27][N:28]([C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][N:32]=4)[C:29]=3[CH3:30])=[O:24])=[CH:18][CH:17]=2)[CH2:11][CH2:12][N:13]([S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])[CH2:14][CH2:15]1)#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 824082-Propanesulfonyl chloride2×HCID 86692605HCID 86692605, compound

Product 1

HCID 86692624HCID 86692624, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isopropylsulfonyl chloride (72 μl) was added to a suspension of N-[6-(4-cyanopiperidin-4-yl)pyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (227 mg) described in Reference Example 169 and potassium carbonate (138 mg) in N,N-dimethylformamide (1.7 ml) and stirred at room temperature for six hours. Then, potassium carbonate (276 mg) and isopropylsulfonyl chloride (144 μl) were added and stirred at room temperature for 0.5 hours. Water was added to the reaction solution and the precipitated solid was washed with water, ethanol and ethyl acetate to give the titled compound (151 mg) as a white solid.

Workup

  1. stirringstirred at room temperature for 0.5 hours
  2. washthe precipitated solid was washed with water, ethanol and ethyl acetate

Sources & evidence

ORD record
ord-e0708bd9241c46d59a202879745184ef
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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