Water → 6-Methyl-2-oxo-1-(3-trifluoromethylphenyl)-1,2-dihydro-pyridine-3-carboxylic acid (3-methyl-isoxazol-5-ylmethyl)-amide

HRID 559821노트

반응식

HRID 559821 반응식
[CH2:1]([NH:4][C:5]([C:7]1[C:8](=[O:24])[N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C:10]([CH3:13])=[CH:11][CH:12]=1)=[O:6])[C:2]#[CH:3].[OH:25][N:26]=[C:27](Cl)[CH3:28].O>CCOC(C)=O>[CH3:28][C:27]1[CH:3]=[C:2]([CH2:1][NH:4][C:5]([C:7]2[C:8](=[O:24])[N:9]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=3)[C:10]([CH3:13])=[CH:11][CH:12]=2)=[O:6])[O:25][N:26]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 69633Ethanimidoyl chloride, N-hydroxy-HCID 866147846-Methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid prop-2-ynylamide

생성물 1

HCID 667254586-Methyl-2-oxo-1-(3-trifluoromethylphenyl)-1,2-dihydro-pyridine-3-carboxylic acid (3-methyl-isoxazol-5-ylmethyl)-amide수율 53%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

The compound obtained in step (a) (0.050 g, 0.15 mmol) was dissolved in EtOAc (15 ml) under magnetic stirring. To this solution was added N-hydroxyacetimidoyl chloride (0.15 g, 1.6 mmol), water (0.3 ml) and KHCO3 (0.16 g, 1.6 mmol). The mixture was stirred for 2 days at which time LC-MS showed 90% conversion. The reaction was stopped and the mixture was partitioned between EtOAc (25 ml) and water (25 ml). The organic phase was washed (water, brine) and dried. Filtration and evaporation gave a crude mixture which was purified by chromatography on silica. Freeze-drying the pure fractions afforded the subtitle compound (0.031 g, 53%) as a white powder.

후처리

  1. customthe mixture was partitioned between EtOAc (25 ml) and water (25 ml)
  2. washThe organic phase was washed (water, brine)
  3. customdried
  4. filtrationFiltration and evaporation
  5. customgave a crude mixture which
  6. customwas purified by chromatography on silica
  7. customFreeze-drying the pure fractions

출처 및 근거

ORD 기록
ord-58f5b44017ee4ec284af8213ea33e467
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063073B2

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