4-Fluorobenzylamine → HCID 54730366, compound

HRID 536121Notes

Reaction equation

HRID 536121 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-α]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-α]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-e19a3e5d58a74128a8f06f71b40147e4
Source dataset
uspto-grants-2014_10
Patent number
US08859563B2

Reaction notes

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