Pyridine → 7-{[2-(4-Trifluoromethyl-phenyl)-pyridine-3-carbonyl]-amino}-quinoline-3-carboxylic acid ethyl ester

HRID 51917

반응식

HRID 51917 반응식
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.[CH2:26]([O:28][C:29]([C:31]1[CH:32]=[N:33][C:34]2[C:39]([CH:40]=1)=[CH:38][CH:37]=[C:36]([NH2:41])[CH:35]=2)=[O:30])[CH3:27].N1C=CC=CC=1>ClCCl.CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl.CN(C)C=O>[CH2:26]([O:28][C:29]([C:31]1[CH:32]=[N:33][C:34]2[C:39]([CH:40]=1)=[CH:38][CH:37]=[C:36]([NH:41][C:11]([C:10]1[C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:18])=[CH:8][CH:7]=3)=[N:17][CH:16]=[CH:15][CH:14]=1)=[O:13])[CH:35]=2)=[O:30])[CH3:27]

참가 물질

9

반응물 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 9877801Ethyl 7-aminoquinoline-3-carboxylateHCID 222627192-(4-Trifluoromethylphenyl)nicotinic acid

생성물 1

HCID 698915467-{[2-(4-Trifluoromethyl-phenyl)-pyridine-3-carbonyl]-amino}-quinoline-3-carboxylic acid ethyl ester수율 122.5%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 6212Chloroform용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

2-(4-Trifluoromethyl-phenyl)-nicotinic acid (534 mg, 2.0 mmol) was suspended in 10 ml of dichloromethane, and oxalyl chloride (0.7 ml, 8.0 mmol) was added followed by a drop of dimethylformamide. After 2 h at room temperature, the volatiles were removed under vacuum, and to the residue was added 10 ml of chloroform, 7-amino-quinoline-3-carboxylic acid ethyl ester (216 mg, 1.0 mmol), pyridine (0.2 ml, 2.5 mmol) and 4-dimethylaminopyridine (12 mg, 0.1 mmol). After heating at reflux overnight, the reaction mixture was diluted with 50 ml of dichloromethane, washed with 35 ml of 2N NaOH, water, dried (magnesium sulfate) filtered, and concentrated under vacuum to afford 570 mg of a brown gum. This material was purified by silica gel chromatography eluting with 50 to 80% ethyl acetate in hexanes to provide 189 mg of the title compound as a light yellow solid.

후처리

  1. customthe volatiles were removed under vacuum
  2. temperatureAfter heating
  3. temperatureat reflux overnight
  4. washwashed with 35 ml of 2N NaOH, water
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-cbc8bdeea37c404a82f9d02512426e9e
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713489B2

연결된 노트

불러오는 중…