2,3-Dimethoxybenzylamine → 5-bromo-N-(2,3-dimethoxybenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

HRID 897292Notes

Reaction equation

HRID 897292 reaction equation
C([O:9][C:10]1[C:11]([C:21]([O:23]C)=O)=[N:12][C:13]([Br:20])=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2)(=O)C1C=CC=CC=1.[CH3:25][O:26][C:27]1[C:34]([O:35][CH3:36])=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29][NH2:30]>C1(C)C=CC=CC=1>[Br:20][C:13]1[N:12]=[C:11]([C:21]([NH:30][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[C:34]([O:35][CH3:36])[C:27]=2[O:26][CH3:25])=[O:23])[C:10]([OH:9])=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[N:18]2

Participants

4

Reactant 2

HCID 781062,3-DimethoxybenzylamineHCID 22346355Methyl 8-(benzoyloxy)-5-bromo-1,6-naphthyridine-7-carboxylate

Product 1

HCID 223463785-bromo-N-(2,3-dimethoxybenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a round bottom flask fitted with a gas inlet, condenser and a magnetic stirring bar was placed methyl 8-(benzoyloxy)-5-bromo-1,6-naphthyridine-7-carboxylate (0.4 g, 1.03 mmol), 2,3-dimethoxybenzylamine (0.432 g, 0.38 mL, 2.58 mmol) and 10 mL toluene. This mixture was refluxed for 18 hours, after which the reaction was cooled and the solvent removed in vacuo. The resulting residue was triturated with diethyl ether and filtered to yield 5-bromo-N-(2,3-dimethoxybenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide as a light yellow solid.

Workup

  1. customInto a round bottom flask fitted with a gas inlet, condenser and a magnetic stirring bar
  2. temperatureThis mixture was refluxed for 18 hours
  3. temperatureafter which the reaction was cooled
  4. customthe solvent removed in vacuo
  5. customThe resulting residue was triturated with diethyl ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-aaf85202a0f74990964b7d6b01f8c0e4
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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