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

HRID 1748673Notes

Reaction equation

HRID 1748673 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]([C:34]2[CH2:35][CH2:36][NH:37][CH2:38][CH:39]=2)=[C:31]([CH3:33])[CH:32]=1)=[O:25].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=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]([C:34]2[CH2:35][CH2:36][N:37]([S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])[CH2:38][CH:39]=2)=[C:31]([CH3:33])[CH:32]=1)=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 824082-Propanesulfonyl chlorideHCID 866925385-Methyl-N-[5-methyl-6-(1,2,3,6-tetrahydropyridin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Product 1

HCID 866926195-Methyl-N-{5-methyl-6-[1-(propane-2-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]pyridin-3-yl}-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isopropylsulfonyl chloride (72 μl) was added to a suspension of 5-methyl-N-[5-methyl-6-(1,2,3,6-tetrahydropyridin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (221 mg) described in Reference Example 170 and potassium carbonate (138 mg) in N,N-dimethylformamide (1.7 ml), and stirred at room temperature for 5 hours. Water was added and the precipitated solid was purified with silica gel chromatography (chloroform/methanol) to give the titled compound (62 mg) as a white solid.

Workup

  1. customthe precipitated solid was purified with silica gel chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-c6c9d3892088417f805f632a1e2b7a69
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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