Water → 5-(4Trifluoromethyl-phenylamino)-2-(3-trifluoromethyl-pyridin-2-yl)-[1,6]napthyridine-7-carboxylic acid ethyl ester

HRID 2113632ノート

反応式

HRID 2113632 の反応式
[CH2:1]([O:3][C:4](=[O:26])[C:5](=O)[CH2:6][C:7]1[N:12]=[C:11]([C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:10]=[CH:9][C:8]=1[C:23]#[N:24])[CH3:2].[F:27][C:28]([F:37])([F:36])[C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1.O>CC(O)=O>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]2[C:8]([CH:9]=[CH:10][C:11]([C:13]3[C:18]([C:19]([F:20])([F:22])[F:21])=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:12]2)=[C:23]([NH:33][C:32]2[CH:34]=[CH:35][C:29]([C:28]([F:36])([F:37])[F:27])=[CH:30][CH:31]=2)[N:24]=1)=[O:26])[CH3:2]

参加物

5

反応物 3

HCID 962WaterHCID 99644-(Trifluoromethyl)anilineHCID 586282123-(5-Cyano-3'-trifluoromethyl-[2,2']bipyridinyl-6-yl)-2-oxo-propionic acid ethyl ester

生成物 1

HCID 586281885-(4Trifluoromethyl-phenylamino)-2-(3-trifluoromethyl-pyridin-2-yl)-[1,6]napthyridine-7-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

Dissolve 3-(5-cyano-3′-trifluoromethyl-[2,2′]bipyridinyl-6-yl)-2-oxo-propionic acid ethyl ester (70 mg, 0.193 mmol) and 4-trifluoromethyl aniline (31 mg, 0.193 mmol) in AcOH (1 mL). Heat the mixture at 100° C. for 1.5 hours. Cool the mixture in ice and add H2O (5 mL). Extract three times with EtOAC (3×10 mL). Combine the organic extracts and wash with 1 N NaOH (30 mL) and brine (30 mL). Dry the organic extract over Na2SO4 and remove the solvent under reduced pressure. Purify the crude product using silica gel chromatography eluting with hexane/acetone (3:1) to yield the title compound. MS 507.15 (M+1)

後処理

  1. temperatureCool the mixture in ice
  2. extractionExtract three times with EtOAC (3×10 mL)
  3. washCombine the organic extracts and wash with 1 N NaOH (30 mL) and brine (30 mL)
  4. customDry the
  5. extractionorganic extract over Na2SO4
  6. customremove the solvent under reduced pressure
  7. customPurify the crude product
  8. washeluting with hexane/acetone (3:1)

出典と根拠

ORDレコード
ord-41689ba245134ed1ac1bef4f37853b98
出典データセット
uspto-grants-2008_10
特許番号
US07432275B2

反応ノート

読み込み中…