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

HRID 559821

反応式

HRID 559821 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-58f5b44017ee4ec284af8213ea33e467
出典データセット
uspto-grants-2011_11
特許番号
US08063073B2

関連ノート

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