N-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-7-methoxy-1-methyl-4-oxo-1,8-naphthyridine-3-carboxamide → N-[(4-chlorophenyl)methyl]-6-(3-hydroxypropyl)-7-methoxy-1-methyl-4-oxo-1,8-naphthyridine-3-carboxamide

HRID 2120777Notes

Reaction equation

HRID 2120777 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[N:14][C:15]([O:25][CH3:26])=[C:16]([C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH3:27])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1>CCO.O=[Pt]=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[N:14][C:15]([O:25][CH3:26])=[C:16]([CH2:21][CH2:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH3:27])[CH:11]=2)=[O:9])=[CH:28][CH:29]=1

Participants

4

Reactant 1

HCID 5276332N-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-7-methoxy-1-methyl-4-oxo-1,8-naphthyridine-3-carboxamide

Product 1

HCID 3010834N-[(4-chlorophenyl)methyl]-6-(3-hydroxypropyl)-7-methoxy-1-methyl-4-oxo-1,8-naphthyridine-3-carboxamideYield 30.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

N-(4-Chlorobenzyl)-6-(3-hydroxy-1-propynyl)-7-methoxy-1-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamide (180 mg) is suspended in EtOH (50 mL) and PtO2 is added. The mixture is shaken under an atmosphere of H2 (45 psi) for 2 h. The solution is filtered through Celite, and concentrated in vacuo. The residue is purified by silica gel chromatography (CH2Cl2/MeOH 1/0, 45/1, 19/1) and recrystallyzed from MeOH to afford 55 mg of N-(4-chlorobenzyl)-6-(3-hydroxypropyl)-7-methoxy-1-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamide. Physical characteristics are as follows: 1H NMR (CDCl3) δ10.49-10.46, 8.82, 7.35-7.30, 4.66, 4.12, 4.00, 3.71, 2.81, 1.98-1.88; IR (diffuse reflectance) 2350, 2317, 1940, 1921, 1916, 1663, 1617, 1568, 1550, 1516, 1456, 1397, 1385, 1283, 809, cm−1; MS (El) m/z 414 (M+), 415, 276, 275, 249, 248, 246, 140, 84, 77, 57.

Workup

  1. filtrationThe solution is filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe residue is purified by silica gel chromatography (CH2Cl2/MeOH 1/0, 45/1, 19/1)

Sources & evidence

ORD record
ord-04806f6bd7284d3ab89ba124108f9239
Source dataset
uspto-grants-2004_02
Patent number
US06693114B2

Reaction notes

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