Potassium Carbonate → 3-[4-Chloro-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[1-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one

HRID 522331노트

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HRID 522331 반응식
Br[CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[N:9][N:10]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[C:11]=2[CH:12]([CH3:14])[CH3:13])[C:3]1=[O:22].[Cl:23][C:24]1[C:25]([CH3:33])=[N:26][NH:27][C:28]=1[C:29]([F:32])([F:31])[F:30].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:23][C:24]1[C:28]([C:29]([F:31])([F:30])[F:32])=[N:27][N:26]([CH:2]2[CH2:6][CH2:5][N:4]([C:7]3[CH:8]=[N:9][N:10]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=4)[C:11]=3[CH:12]([CH3:14])[CH3:13])[C:3]2=[O:22])[C:25]=1[CH3:33]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 867230453-Bromo-1-[1-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-oneHCID 178434610HCID 178434610, 화합물

생성물 1

HCID 867230443-[4-Chloro-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[1-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

A mixture of 3-bromo-1-[1-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (0.035 g, 0.095 mmol), 4-chloro-3-methyl-5-(trifluoromethyl)-1H-pyrazole (0.050 g, 0.27 mmol) and K2CO3 (0.050 g, 0.36 mmol) in DMF (0.8 mL) was stirred at 60° C. for 40 min. The mixture was then cooled to room temperature, quenched with water (30 mL), extracted with EtOAc (50 mL), and purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to yield the title compound (0.036 g, 78%). 1H NMR (400 MHz, CDCl3) δ 7.57 (s, 1H), 7.47 (m, 2H), 7.34 (m, 2H), 5.05 (dd, J=9.2, 6.0 Hz, 1H), 4.04 (m, 1H), 3.81 (m, 1H), 2.99 (heptet, J=6.8 Hz, 1H), 2.87 (m, 1H), 2.76 (m, 1H), 2.42 (s, 3H), 1.22 (d, J=7.2 Hz, 3H), 1.12 (d, J=7.2 Hz, 3H); MS: (ES) m/z calculated for C21H20Cl2F3N5O [M+H]+486.1. found 486.1.

후처리

  1. temperatureThe mixture was then cooled to room temperature
  2. customquenched with water (30 mL)
  3. extractionextracted with EtOAc (50 mL)
  4. custompurified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

출처 및 근거

ORD 기록
ord-aebbadaf7daa47489b9c2295ae4cb015
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328116B2

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