Potassium Carbonate → HCID 69675034, compound

HRID 2206848Notes

Reaction equation

[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([F:10])[F:9])[C:3]=1[C:11](Cl)=[O:12].[CH3:14][CH:15]([CH3:26])[CH2:16][CH:17]([C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([F:10])[F:9])[C:3]=1[C:11]([NH:21][C:20]1[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=1[CH:17]([CH2:16][CH:15]([CH3:26])[CH3:14])[CH3:18])=[O:12]

Participants

Conditions

Temperature: 20 °C

Procedure

0.458 g (2.00 mmol) of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride is added to a mixture of 0.322 g (1.81 mmol) of 2-(4-methylpentan-2-yl)aniline and 0.377 g (2.72 mmol) of potassium carbonate in 30 mL of acetonitrile, and the mixture is stirred at 20° C. overnight. After the reaction has ended, the mixture is extracted with water/ethyl acetate. The organic phase is dried with sodium sulfate and concentrated under reduced pressure. The crude product is purified by column chromatography (mobile phase: cyclohexane/ethyl acetate gradient). This gives 0.580 g (78% of theory) of 5-chloro-3-(difluoromethyl)-1-methyl-N-[2-(4-methylpentan-2-yl)phenyl]-1H-pyrazole-4-carboxamide having a content of 94% according to LC-MS and a logP (acidic) of 4.01.

Workup

extractionthe mixture is extracted with water/ethyl acetate
dry with materialThe organic phase is dried with sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude product is purified by column chromatography (mobile phase: cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record: ord-76a63c2dc6544cbdb9cba76223ad0056
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09375004B2

Reaction notes

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