Triethylamine → 5-Methyl-N-{5-methyl-6-[1-(propane-2-sulfonyl)piperidin-4-yl]pyridin-3-yl}-1-[5-(trifluoromethyl) pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748679Notes

Reaction equation

HRID 1748679 reaction equation
[CH:1]([S:4](Cl)(=[O:6])=[O:5])([CH3:3])[CH3:2].[CH3:8][C:9]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=2)[N:12]=[CH:11][C:10]=1[C:24]([NH:26][C:27]1[CH:28]=[N:29][C:30]([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[C:31]([CH3:33])[CH:32]=1)=[O:25].C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C>CN(C)C=O.O>[CH3:8][C:9]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:16][N:15]=2)[N:12]=[CH:11][C:10]=1[C:24]([NH:26][C:27]1[CH:28]=[N:29][C:30]([CH:34]2[CH2:35][CH2:36][N:37]([S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])[CH2:38][CH2:39]2)=[C:31]([CH3:33])[CH:32]=1)=[O:25]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 824082-Propanesulfonyl 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 866926265-Methyl-N-{5-methyl-6-[1-(propane-2-sulfonyl)piperidin-4-yl]pyridin-3-yl}-1-[5-(trifluoromethyl) pyridin-2-yl]-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Isopropylsulfonyl chloride (72 μl) was added to a suspension 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 potassium carbonate (138 mg) in N,N-dimethylformamide (1.7 ml) and stirred at room temperature for an hour. Then, isopropylsulfonyl chloride (36 μl) was added and stirred at room temperature for two hours. Triethylamine (350 μl) and water were added and the precipitated solid was washed with ethanol and water. The resulting solid was purified with silica gel chromatography (chloroform/methanol) to give the titled compound (103 mg) as a white solid.

Workup

  1. stirringstirred at room temperature for two hours
  2. washthe precipitated solid was washed with ethanol and water
  3. customThe resulting solid was purified with silica gel chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-364f4f63a60f45e3bc5227390731b595
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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