Dimethylformamide → 1-(5-trifluoromethylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxamide

HRID 1748630Notes

Reaction equation

S(Cl)(Cl)=O.C[N:6](C)[CH:7]=[O:8].[CH3:10][C:11]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=2)[N:14]=[CH:13][C:12]=1C(O)=O>C1(C)C=CC=CC=1>[CH3:10][C:11]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:18][N:17]=2)[N:14]=[CH:13][C:12]=1[C:7]([NH2:6])=[O:8]

Participants

Conditions

Temperature: 80 °C

Procedure

Thionyl chloride (3.95 g) and N,N-dimethylformamide (catalytic amounts) were added at room temperature to 5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid (3.0 g) described in Reference Example 8 in toluene (55 ml), and stirred at 80° C. for an hour. The solvent and an excess amount of thionyl chloride were evaporated, tetrahydrofuran (55 ml) was added to the residue, 25% aqueous ammonia (44 ml) was added under ice-cooling and stirred at room temperature for two hours. After the reaction, 1N aqueous solution of sodium hydroxide was added, and the precipitated solid was filtered to give 5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (2.9 g) as a white solid.

Workup

customThe solvent and an excess amount of thionyl chloride were evaporated
additiontetrahydrofuran (55 ml) was added to the residue, 25% aqueous ammonia (44 ml)
additionwas added under ice-
temperaturecooling
stirringstirred at room temperature for two hours
customAfter the reaction, 1N aqueous solution of sodium hydroxide
additionwas added
filtrationthe precipitated solid was filtered

Sources & evidence

ORD record: ord-a51680eaf6444ce5975c1b11d4a14fb9
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150555B2

Reaction notes

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