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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
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HRID 1411113 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5510be306e6648db928075437b574242
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08921575B2

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