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

HRID 1748668Notes

Reaction equation

[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=2)[N:9]=[CH:8][C:7]=1[C:21]([NH:23][C:24]1[CH:25]=[N:26][C:27]([C:31]2[CH2:32][CH2:33][NH:34][CH2:35][CH:36]=2)=[C:28]([CH3:30])[CH:29]=1)=[O:22].O>N1C=CC=CC=1>[C:1]([N:34]1[CH2:35][CH:36]=[C:31]([C:27]2[N:26]=[CH:25][C:24]([NH:23][C:21]([C:7]3[CH:8]=[N:9][N:10]([C:11]4[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=4)[C:6]=3[CH3:5])=[O:22])=[CH:29][C:28]=2[CH3:30])[CH2:32][CH2:33]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

Acetyl chloride (50 μl) was added to a solution 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 (300 mg) described in Reference Example 170 in pyridine (3.4 ml), stirred at 40° C. for six hours. Acetyl chloride (50 μl) was added and stirred for two hours, and then, Acetyl chloride (50 μl) was added and stirred for six hours. Water was added to the reaction solution and the precipitated solid was washed with ethanol and water to give the titled compound (283 mg) as a pale yellow solid.

Workup

stirringstirred for two hours
stirringstirred for six hours
washthe precipitated solid was washed with ethanol and water

Sources & evidence

ORD record: ord-4204cf54170a4f7a8a0eae2e3875fd87
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150555B2

Reaction notes

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