4-Chlorobenzylamine → HCID 490481, compound

HRID 1068051Notes

Reaction equation

HRID 1068051 reaction equation
[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

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 21192562HCID 21192562, compound

Product 1

HCID 490481HCID 490481, compound

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f8df5206534348c096e9cb4c04bdafcc
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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