Water → N-[2-(isopropoxymethyl)phenyl]-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-carboxamide

HRID 1176011ノート

反応式

HRID 1176011 の反応式
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([C:14]1[C:15]([C:20]([F:23])([F:22])[F:21])=[N:16][N:17]([CH3:19])[CH:18]=1)=[O:13].I[CH:25]([CH3:27])[CH3:26].O>CN(C)C=O.CO>[CH:25]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([C:14]1[C:15]([C:20]([F:23])([F:22])[F:21])=[N:16][N:17]([CH3:19])[CH:18]=1)=[O:13])([CH3:27])[CH3:26]

参加物

7

反応物 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 22980801N-[2-(hydroxymethyl)phenyl]-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide

生成物 1

HCID 59559824N-[2-(isopropoxymethyl)phenyl]-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-carboxamide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

156.0 mg (3.9 mmol) of 60% sodium hydride in oil are added to a solution of 897.8 mg (3.0 mmol) N-[2-(hydroxymethyl)phenyl]-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide (IV-1) in 2 ml dimethyl formamide at room temperature. After 30 minutes, 0.6 ml (6.0 mmol) 2-iodopropane are added. The reaction mixture is stirred for 6 hours at 100° C. and thereafter for 16 hours at room temperature. Afterward, the mixture is diluted with 1 ml methanol, added to water and extracted with ethyl acetate; the organic phase is dried over magnesium sulfate, the drying agent filtered off and the material concentrated under vacuum. Column chromatography (3:1 cyclohexane/ethyl acetate) yielded 100.0 mg (9.7% of the theoretical yield) of N-[2-(isopropoxymethyl)phenyl]-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-carboxamide [logP (pH 2.3)=2.85].

後処理

  1. waitfor 16 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationthe drying agent filtered off
  5. concentrationthe material concentrated under vacuum
  6. customColumn chromatography (3:1 cyclohexane/ethyl acetate) yielded 100.0 mg (9.7% of the

出典と根拠

ORDレコード
ord-08b59c829b42495ba7201e6a5b92df67
出典データセット
uspto-grants-2010_11
特許番号
US07842710B2

反応ノート

読み込み中…