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

HRID 841776

反応式

HRID 841776 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 24386Thionyl Chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c2a6f9c07db64467a438da7fa0104db3
出典データセット
uspto-grants-2002_04
特許番号
US06369075B1

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