Triethylamine → N-(2-methylthiobenzyl)-2-[1,6]naphthyridine carboxamide

HRID 1383419Notes

Reaction equation

HRID 1383419 reaction equation
Cl.[CH3:2][S:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][NH2:7].C(N(CC)CC)C.[N:19]1[C:28]2[C:23](=[CH:24][N:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[C:29](O)=[O:30].O.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[CH3:2][S:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][NH:7][C:29]([C:20]1[CH:21]=[CH:22][C:23]2[C:28](=[CH:27][CH:26]=[N:25][CH:24]=2)[N:19]=1)=[O:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 186213292-Methylsulfanylbenzylamine hydrochloride

Product 1

HCID 18621307N-(2-methylthiobenzyl)-2-[1,6]naphthyridine carboxamideYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of 2-methylsulfanylbenzylamine hydrochloride (81.7 mg, 0.431) in anhydrous DMF (1.0 mL) was added triethylamine (60.0 μL, 0.431 mmol). After 5 minutes, 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol), 1-hydroxybenzotriazole hydrate (42.7 mg, 0.316 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarboiimide hydrochloride (61.8 mg, 0.316 mmol) were added sequentially. The resulting mixture was allowed to stir at room temperature overnight. 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 light brown solid (88.2 mg, 99%): m.p. 102-103° C.

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-6fb29a730e5f4788ae7a32fad03ad624
Source dataset
uspto-grants-2001_07
Patent number
US06255318B1

Reaction notes

Loading…