Water → N-{1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methyl-1-oxopropan-2-yl}-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide

HRID 589301Notes

Reaction equation

HRID 589301 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]([CH3:24])([CH3:23])[C:10]([C:12]1[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][N:13]=1)=[O:11].[F:25][CH:26]([F:37])[C:27]1[C:31]([C:32](Cl)=[O:33])=[C:30]([F:35])[N:29]([CH3:36])[N:28]=1.O>ClCCl>[Cl:18][C:17]1[C:12]([C:10](=[O:11])[C:9]([NH:8][C:32]([C:31]2[C:27]([CH:26]([F:37])[F:25])=[N:28][N:29]([CH3:36])[C:30]=2[F:35])=[O:33])([CH3:24])[CH3:23])=[N:13][CH:14]=[C:15]([C:19]([F:21])([F:22])[F:20])[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 529205085-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbonyl chlorideHCID 866856712-Amino-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methylpropan-1-one

Product 1

HCID 86685670N-{1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methyl-1-oxopropan-2-yl}-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamideYield 21.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 13 ml Chemspeed™ vial is weighted 73 mg (0.726 mmol) of triethylamine. 3 ml of a 0.23 molar solution of 2-amino-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methylpropan-1-one (0.594 mmole) in dichloromethane is added followed by 3 ml of a 0.26 molar solution of 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl chloride (0.66 mmole) in dichloro-methane and stirred at ambient temperature for 15 hrs. 1 ml of water is then added and the mixture is deposited on a basic alumina cartridge (2 g) and eluted twice by 8 ml of dichloromethane. The solvents are removed to yield 57 mg (19%) of pure N-{1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methyl-1-oxopropan-2-yl}-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide as an oil (M+H=443).

Workup

  1. washeluted twice by 8 ml of dichloromethane
  2. customThe solvents are removed

Sources & evidence

ORD record
ord-aaec61b4581d4b1eb432c6efea936b4a
Source dataset
uspto-grants-2016_01
Patent number
US09232799B2

Reaction notes

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