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

HRID 522331ノート

反応式

HRID 522331 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-aebbadaf7daa47489b9c2295ae4cb015
出典データセット
uspto-grants-2016_05
特許番号
US09328116B2

反応ノート

読み込み中…