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Potassium Carbonate → N-{2-[1,1'-bi(cyclopropyl)-2-yl]cyclohexyl}-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide

HRID 1411113
Notes
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Reaction equation

HRID 1411113 reaction equation
[CH:1]1([CH:11]2[CH2:13][CH2:12]2)[CH2:3][CH:2]1[CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[NH2:10].C(=O)([O-])[O-].[K+].[K+].[F:20][CH:21]([F:32])[C:22]1[C:26]([C:27](Cl)=[O:28])=[C:25]([F:30])[N:24]([CH3:31])[N:23]=1>C(#N)C>[CH:1]1([CH:11]2[CH2:13][CH2:12]2)[CH2:3][CH:2]1[CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[NH:10][C:27]([C:26]1[C:22]([CH:21]([F:32])[F:20])=[N:23][N:24]([CH3:31])[C:25]=1[F:30])=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 529205085-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbonyl chlorideHCID 86685672HCID 86685672, compound

Product 1

HCID 86685673N-{2-[1,1'-bi(cyclopropyl)-2-yl]cyclohexyl}-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamideYield 41.2%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

To a mixture of 0.489 g (2.73 mmol) 2-[1,1′-bi(cyclopropyl)-2-yl]cyclohexanamine and 0.565 g (4.09 mmol) potassiumcarbonate in 30 ml Acetonitrile was added 0.638 g (3.00 mmol) 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl chloride and stirred at ambient temperature over night. At the end of the reaction the reaction mixture was extracted with ethylacetate and water. The organic layer was dried with natriumsulfate and the solvent was removed by vacuum. The crude product was purified by column chromathography (Solvent: Cyclohexane/ethylacetate gradient). Finally 0.40 g (33%) of N-{2-[1,1′-bi(cyclopropyl)-2-yl]cyclohexyl}-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide with a purity of 87% LC-MS was isolated. logP (acid) of 4.02.

Workup

  1. customAt the end of the reaction the reaction mixture
  2. extractionwas extracted with ethylacetate and water
  3. dry with materialThe organic layer was dried with natriumsulfate
  4. customthe solvent was removed by vacuum
  5. customThe crude product was purified by column chromathography (Solvent: Cyclohexane/ethylacetate gradient)

Sources & evidence

ORD record
ord-5510be306e6648db928075437b574242
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921575B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes