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

HRID 1176011노트

반응식

HRID 1176011 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-08b59c829b42495ba7201e6a5b92df67
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842710B2

반응 노트

불러오는 중…