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

HRID 2113632노트

반응식

HRID 2113632 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-41689ba245134ed1ac1bef4f37853b98
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432275B2

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