4-Fluorobenzylamine → HCID 54730366, compound

HRID 1097747Notes

Reaction equation

HRID 1097747 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:8]2[C:9](=[O:12])[C:10]=1[OH:11])=[O:4].[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>CO>[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:3]([C:5]2[N:6]=[C:7]3[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:8]3[C:9](=[O:12])[C:10]=2[OH:11])=[O:4])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 57494523HCID 57494523, compound

Product 1

HCID 54730366HCID 54730366, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Bromo-3-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid methyl ester (20 mg, 0.07 mmol) and p-fluorobenzylamine (19 uL, 0.17 mmol) in dry methanol (4 mL) was heated to reflux with stirring. Reaction progress was monitored by HPLC. After 6 h, the reaction was cooled to room temperature and concentrated in vacuo. The residue was triturated with diethyl ether (2 mL) and the precipitate collected by filtration and washed with diethyl ether (10 mL) and dried on the pump to afford 7-bromo-3-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid 4-fluoro-benzylamide (24 mg, 92%) as a yellow brown solid.

Workup

  1. temperatureto reflux
  2. customReaction progress
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with diethyl ether (2 mL)
  5. filtrationthe precipitate collected by filtration
  6. washwashed with diethyl ether (10 mL)
  7. customdried on the pump

Sources & evidence

ORD record
ord-3e5005a654c04ea393bace91a51e6b20
Source dataset
uspto-grants-2012_03
Patent number
US08143268B2

Reaction notes

Loading…