4-Fluorobenzylamine → N-(4-fluorobenzyl)4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 1179297Notes

Reaction equation

HRID 1179297 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]([O:15]C)=O.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1>C(O)C.O>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:23][C:13]([C:3]2[C:4](=[O:12])[NH:5][C:6]3[C:11]([C:2]=2[OH:1])=[N:10][CH:9]=[CH:8][CH:7]=3)=[O:15])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 673264-FluorobenzylamineHCID 54729994Methyl 4-Hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 54690727N-(4-fluorobenzyl)4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (0.2 g, 0.91 mmol) and 4-fluorobenzyl amine (Aldrich, 0.31 mL, 2.72 mmol) in absolute ethanol (5 mL) was heated to 100° C. for 6 hours. A thick paste formed. The reaction was diluted with water and the solids collected. The crude material was purified by preparative reverse phase HPLC eluting with a gradient of 5-95% acetonitrile/water (0.1% TFA). The product precipitated from the column fractions was collected to afford the desired product as a white solid.

Workup

  1. customA thick paste formed
  2. customthe solids collected
  3. customThe crude material was purified by preparative reverse phase HPLC
  4. washeluting with a gradient of 5-95% acetonitrile/water (0.1% TFA)
  5. customThe product precipitated from the column fractions
  6. customwas collected

Sources & evidence

ORD record
ord-35b66eb852574345b4a540fd893bb550
Source dataset
uspto-grants-2007_10
Patent number
US07279487B2

Reaction notes

Loading…