1,3-Dimethyl-1H-pyrazole-4-carbonyl chloride → N-(3',4',5'-trifluorobiphenyl-2-yl)-1,3-dimethyl-1H-pyrazole-4-carboxamide

HRID 1803094Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7](Cl)=[O:8])[C:4]([CH3:10])=[N:3]1.[F:11][C:12]1[CH:13]=[C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[NH2:26])[CH:15]=[C:16]([F:19])[C:17]=1[F:18]>C1(C)C=CC=CC=1>[F:11][C:12]1[CH:13]=[C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[NH:26][C:7]([C:5]2[C:4]([CH3:10])=[N:3][N:2]([CH3:1])[CH:6]=2)=[O:8])[CH:15]=[C:16]([F:19])[C:17]=1[F:18]

Participants

Conditions

Temperature: 85 °C

Procedure

79.1 g (0.494 mol, 99% pure) of 1,3-dimethyl-1H-pyrazole-4-carbonyl chloride were dissolved at 25° C. in 257.2 g of toluene. The solution was evacuated to 400 mbar and heated to 85° C. Subsequently, within 3 hours, 483.0 g (0.489 mol, 23% strength) of toluenic 3′,4′,5′-trifluorobiphenyl-2-ylamine solution were metered in and the reaction mixture was stirred for a further 1 hour. After venting and cooling to 70° C., the mixture was cooled to 20° C. with a cooling ramp of 5° C./h and stirred overnight. Subsequently, the mixture was cooled to 0° C., and the solids were filtered off, washed with cold toluene and dried at 80° C. under reduced pressure. The yield (without further processing of the mother liquor) was 155.4 g (92%).

Workup

customThe solution was evacuated to 400 mbar
temperaturecooling to 70° C.
temperaturethe mixture was cooled to 20° C. with a cooling ramp of 5° C./h
stirringstirred overnight
temperatureSubsequently, the mixture was cooled to 0° C.
filtrationthe solids were filtered off
washwashed with cold toluene
customdried at 80° C. under reduced pressure
customThe yield (without further processing of the mother liquor)

Sources & evidence

ORD record: ord-3cb53bd6fc364d6a9c19dba2366665e2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08350046B2

Reaction notes

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