Diisopropylethylamine → 7-[2-(5-Trifluoromethyl-pyridin-2-yl)-benzoylamino]-quinoline-3-carboxylic acid ethyl ester

HRID 841776

반응식

HRID 841776 반응식
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)=[N:7][CH:8]=1.[CH2:20]([O:22][C:23]([C:25]1[CH:26]=[N:27][C:28]2[C:33]([CH:34]=1)=[CH:32][CH:31]=[C:30]([NH2:35])[CH:29]=2)=[O:24])[CH3:21].C(N(C(C)C)CC)(C)C>S(Cl)(Cl)=O.ClCCCl>[CH2:20]([O:22][C:23]([C:25]1[CH:26]=[N:27][C:28]2[C:33]([CH:34]=1)=[CH:32][CH:31]=[C:30]([NH:35][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:18])=[CH:8][N:7]=1)[CH:29]=2)=[O:24])[CH3:21]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 9877801Ethyl 7-aminoquinoline-3-carboxylateHCID 227369092-(5-(Trifluoromethyl)pyridin-2-yl)benzoic acid

생성물 1

HCID 698913457-[2-(5-Trifluoromethyl-pyridin-2-yl)-benzoylamino]-quinoline-3-carboxylic acid ethyl ester수율 85%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 24386Thionyl Chloride용매

실험 절차

2-(5-Trifluoromethyl-pyridin-2-yl)-benzoic acid (325 mg, 1.05 mmol) was dissolved in 15 ml of thionyl chloride, and the mixture heated at 60 C. After 4 h, the volatiles were removed under vacuum, the residue combined with 7-amino-quinoline-3-carboxylic acid ethyl ester (100 mg, 0.46 mmol), dissolved in 1,2-dichloroethane (15 ml), and diisopropylethylamine (300 mg, 2.31 mmol) added. After heating at reflux for 48 h, the reaction mixture was washed with 1N HCl, dried (magnesium sulfate), filtered, and concentrated under vacuum. The resulting residue was purified by silica gel chromatography eluting with 50% ethyl acetate in hexanes to provide 180 mg (85%) of the title compound.

후처리

  1. temperaturethe mixture heated at 60 C
  2. customthe volatiles were removed under vacuum
  3. temperatureAfter heating
  4. temperatureat reflux for 48 h
  5. washthe reaction mixture was washed with 1N HCl
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe resulting residue was purified by silica gel chromatography
  10. washeluting with 50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-c2a6f9c07db64467a438da7fa0104db3
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369075B1

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