Pyridine → 7-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester

HRID 51906

반응식

HRID 51906 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7](N)=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2].[N:17]1C=CC=CC=1.[F:23][C:24]([F:41])([F:40])[C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:32]([C:37](Cl)=[O:38])=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:27][CH:26]=1>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([NH:17][C:37]([C:32]1[C:31]([C:28]3[CH:29]=[CH:30][C:25]([C:24]([F:41])([F:40])[F:23])=[CH:26][CH:27]=3)=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:38])[CH:10]=2)=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 283477Ethyl 2-aminoquinoline-3-carboxylateHCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chloride

생성물 1

HCID 101832717-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester수율 159.1%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

7-[Amino-quinoline-3-carboxylic acid ethyl ester (8.6 g, 39.8 mmol) was combined with pyridine (12.9 ml, 159 mmol) and 4-N,N-dimethylamino-pyridine (0.5 g, 4 mmol) in 100 ml of chloroform. The mixture was stirred as 4′-trifluoromethyl-biphenyl-2-carbonyl chloride (22.64 g, 79.5 mmol) was added as a solution in 100 ml of chloroform. After heating at reflux for 2 h, the mixture was concentrated under vacuum, the residue taken up in ethyl acetate (600 ml) and washed sequentially with a 1 N aqueous hydrochloric acid solution (2×200 ml), water, and brine. The organic phase was then dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to yield 29.4 g of a red oil. This oil was purified by chromatography on silica, eluting sequentially with a 70:30 dichloromethanelhexanes solution, followed by dichloromethane, then a 10:90 ethyl acetate/dichloromethane solution. Concentration under vacuum of the product containing fractions afforded 13.15 g of the title compound as a yellow solid.

후처리

  1. temperatureAfter heating
  2. temperatureat reflux for 2 h
  3. concentrationthe mixture was concentrated under vacuum
  4. washwashed sequentially with a 1 N aqueous hydrochloric acid solution (2×200 ml), water, and brine
  5. dry with materialThe organic phase was then dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-432f4e22cd9442f5900b57165a71df8a
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713489B2

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