1,6-Naphthyridine-2-carboxylic acid → N-(2,6-dimethoxybenzyl)-2-[1,6]naphthyridine-carboxamide

HRID 1383412Notes

Reaction equation

HRID 1383412 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.O.ON1C2C=CC=CC=2N=N1.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[C:28]=1[CH2:29][NH2:30]>CN(C=O)C>[CH3:36][O:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:27]([O:26][CH3:25])[C:28]=1[CH2:29][NH:30][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

5

Reactant 3

HCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 28008722,6-Dimethoxybenzylamine

Product 1

HCID 18621322N-(2,6-dimethoxybenzyl)-2-[1,6]naphthyridine-carboxamideYield 98%

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 (1.0 mL) at room temperature was added sequentially 1-hydroxybenzotriazole hydrate (42.7 mg, 0.316 mmol), 2,6-dimethoxybenzylamine (75.0 mg, 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 white solid (90.6 mg, 98%): m.p. 169-171° C.

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-13b6992e5bc844009c91227ca1d57a8c
Source dataset
uspto-grants-2001_07
Patent number
US06255318B1

Reaction notes

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