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

HRID 51972

反応式

HRID 51972 の反応式
[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]([NH2:16])[CH:10]=2)=[O:5])[CH3:2].C(N(C(C)C)CC)(C)C.[F:26][C:27]([F:44])([F:43])[C:28]1[CH:33]=[CH:32][C:31]([C:34]2[C:35]([C:40](Cl)=[O:41])=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:30][CH:29]=1.C(OC(C)C)(C)C>ClC(Cl)C.C1(C)C=CC=CC=1>[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:16][C:40]([C:35]1[C:34]([C:31]3[CH:32]=[CH:33][C:28]([C:27]([F:26])([F:43])[F:44])=[CH:29][CH:30]=3)=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:41])[CH:10]=2)=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 7914Diisopropyl EtherHCID 81531DiisopropylethylamineHCID 9877801Ethyl 7-aminoquinoline-3-carboxylateHCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chloride

生成物 1

HCID 101832717-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester収率 58.4%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 63651,1-Dichloroethane溶媒2 回

反応条件

温度
84 °C

実験手順

To a mixture of 7-amino-quinoline-3-carboxylic acid ethyl ester (11 g, 51 mmol, 1 equiv), dichloroethane (220 mL, 20 volumes), and diisopropylethylamine (13.15 g, 101.7 mmol, 2 equiv) was slowly added a solution of 4′-trifluoromethyl-biphenyl -2-carbonyl chloride (17.38 g, 61 mmol, 1.2 equiv) dissolved in dichloroethane (30 mL, 2.7 volumes). The reaction was heated at 84° C. overnight and then cooled to room temperature. The reaction mixture was washed with 1 N hydrochloric acid (2×150 mL) and the aqueous layer was back extracted with dichloroethane (1×150 mL). The combined organic layers were washed with 1 N sodium hydroxide (2×150 mL), water (150 mL), and saturated sodium chloride (2×150 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give a red-brown oil. The oil was dissolved in hot toluene (32 mL) and isopropyl ether (16 mL) and the resulting solution was allowed to cool with stirring to give a beige slurry. The solids were collected by filtration to give 7-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester (13.8 g, 58.4%).

後処理

  1. temperaturecooled to room temperature
  2. washThe reaction mixture was washed with 1 N hydrochloric acid (2×150 mL)
  3. extractionthe aqueous layer was back extracted with dichloroethane (1×150 mL)
  4. washThe combined organic layers were washed with 1 N sodium hydroxide (2×150 mL), water (150 mL), and saturated sodium chloride (2×150 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a red-brown oil
  8. temperatureto cool
  9. customto give a beige slurry
  10. filtrationThe solids were collected by filtration

出典と根拠

ORDレコード
ord-ca88576402484af4b76b9d01a0bfce8c
出典データセット
uspto-grants-2004_03
特許番号
US06713489B2

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