4-Chlorobenzylamine → HCID 490481, 화합물

HRID 1068051노트

반응식

HRID 1068051 반응식
[CH3:1][N:2]([CH3:22])[N:3]1[C:12]2[C:7](=[CH:8][C:9](I)=[CH:10][CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([O:17]CCCC)=O)=[CH:4]1.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:15]([C:5]2[C:6](=[O:14])[C:7]3[C:12](=[CH:11][CH:10]=[C:9]([C:4]#[C:5][CH2:6][OH:14])[CH:8]=3)[N:3]([N:2]([CH3:1])[CH3:22])[CH:4]=2)=[O:17])=[CH:26][CH:25]=1

참가 물질

3

반응물 2

HCID 660364-ChlorobenzylamineHCID 21192562HCID 21192562, 화합물

생성물 1

HCID 490481HCID 490481, 화합물

실험 절차

Butyl 1-(dimethylamino)-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylate (0.50 g) from Preparation No. 58 and 4-chlorobenzylamine (0.29 mL) are heated to 170° C. for 7 hours. The reaction is cooled to rt, and the crude solid is recrystallized in acetic acid yielding 0.54 g of the amide. The resulting amide (0.25 g), copper (I) iodide (30 mg), and bis(triphenylphosphine)palladium (II) chloride (18 mg) are suspended in diethylamine (8 mL). Propargyl alcohol (36 μL) is added and the mixture is allowed to stir at room temperature for 16 h. The mixture is diluted with ethanol and then concentrated in vacuo. The crude solid is triturated with dichloromethane and purified by column chromatography (2% MeOH/CH2Cl2), affording 9 mg of the title compound as a beige solid.

후처리

  1. customthe crude solid is recrystallized in acetic acid yielding 0.54 g of the amide
  2. additionPropargyl alcohol (36 μL) is added
  3. additionThe mixture is diluted with ethanol
  4. concentrationconcentrated in vacuo
  5. customThe crude solid is triturated with dichloromethane
  6. custompurified by column chromatography (2% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-f8df5206534348c096e9cb4c04bdafcc
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248739B1

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