Acetic Acid → 1-Benzyl-8-cyano-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid (pyridin-4-ylmethyl)-amide

HRID 1410735Notes

Reaction equation

HRID 1410735 reaction equation
C[O:2][C:3]([C:5]1[C:6]([OH:31])=[C:7]2[C:12](=[C:13]([C:15]#[N:16])[N:14]=1)[N:11]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:10](=[O:24])[C:9]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[CH:8]2)=O.[NH2:32][CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1.CC(O)=O.O>CCO>[N:37]1[CH:38]=[CH:39][C:34]([CH2:33][NH:32][C:3]([C:5]2[C:6]([OH:31])=[C:7]3[C:12](=[C:13]([C:15]#[N:16])[N:14]=2)[N:11]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:10](=[O:24])[C:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:8]3)=[O:2])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 773174-PyridinemethanamineHCID 682976531-Benzyl-8-cyano-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

Product 1

HCID 867141111-Benzyl-8-cyano-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid (pyridin-4-ylmethyl)-amideYield 43.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-benzyl-8-cyano-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (35 mg, 0.085 mmol) and 4-(aminomethyl)-pyridine (0.030 mL, 0.30 mmol) in 2 mL of EtOH was refluxed for 16 h. AcOH (0.1 mL) and water (4 mL) were added, and the resulting precipitate was isolated by filtration. The crude solid was purified by silica gel chromatography (0-45% EtOAc/CH2Cl2+1% AcOH) to give 18 mg of the title compound as an off-white solid. MS: (+) m/z 488.13 (M+1).

Workup

  1. temperaturewas refluxed for 16 h
  2. customthe resulting precipitate was isolated by filtration
  3. customThe crude solid was purified by silica gel chromatography (0-45% EtOAc/CH2Cl2+1% AcOH)

Sources & evidence

ORD record
ord-988b69a993db47eb937d1ff07f2a599f
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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