Methyl iodide → 6-bromo-N-(4-chlorobenzyl)-1,7-dimethyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamide

HRID 2120767Notes

Reaction equation

HRID 2120767 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[CH3:12])[N:8]=[CH:7][C:6]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[O:14])=[C:5]2[OH:24].[C:25](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[CH3:12])[N:8]([CH3:25])[CH:7]=[C:6]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[O:14])[C:5]2=[O:24]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178432387HCID 178432387, compound

Product 1

HCID 120933136-bromo-N-(4-chlorobenzyl)-1,7-dimethyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamideYield 86.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-N-(4-chlorobenzyl)4-hydroxy-7-methyl[1,8]naphthyridine-3-carboxamide (0.400 g, 0.98 mmol) and potassium carbonate (0.54 g, 3.92 mmol) in 5 mL DMF at room temperature is added dropwise methyl iodide (0.167 g, 1.18 mmol). The mixture is stirred at room temperature for 30 min then diluted with water. The resulting solid is filtered, washed with water and dried. The crude product is triturated with EtOAc/hexanes to yield 0.358 g (85%) of the desired product as a white solid. Physical characteristics are as follows: m.p. 266-268° C.; 1H NMR (CDCl3) δ10.18, 8.92, 8.83, 7.30, 4.65, 4.03, 2.82; Anal. Calcd for C18H15BrClN3O2: C, 51.39; H, 3.59; N, 9.99; Found: C, 51.02; H, 3.57; N, 9.94.

Workup

  1. filtrationThe resulting solid is filtered
  2. washwashed with water
  3. customdried
  4. customThe crude product is triturated with EtOAc/hexanes

Sources & evidence

ORD record
ord-169c04b34bdb47a2a2ba9f1bb11cc50a
Source dataset
uspto-grants-2004_02
Patent number
US06693114B2

Reaction notes

Loading…