3-Methoxybenzylamine → N-[(3-methoxyphenyl)methyl]-1,6-naphthyridine-2-carboxamide

HRID 1586511Notes

Reaction equation

HRID 1586511 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH2:20]>CN(C=O)C>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH:20][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[N:7][CH:6]=2)[N:1]=1)=[O:13]

Participants

4

Reactant 2

HCID 211563-MethoxybenzylamineHCID 7359081,6-Naphthyridine-2-carboxylic acid

Product 1

HCID 484991N-[(3-methoxyphenyl)methyl]-1,6-naphthyridine-2-carboxamideYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol) in anhydrous DMF (10 mL) at room temperature was added sequentially 1-hydroxyhenzotriazole hydrate (42.7 mg, 0.316 mmol), 3-methoxybenzylamine (56.6 μL, 0.431 mmol) and 1-(3-dimethylaminopropyl-3-ethylcarboiimide hydrochloride (61.8 mg, 0.316 mmol). The resulting mixture was allowed to stir at room temperature overnight and it was found to be clear. The solvent was removed under vacuum. Flash column chromatography of the residue (50% hexane/ethyl acetate to 100% ethyl acetate) afforded the desired product as a clear oil (79.1 mg, 94%).

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-61824b0d7c284575bea57cbcfd0f7c0e
Source dataset
uspto-grants-1999_08
Patent number
US05945431

Reaction notes

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