Triethylamine → HCID 117667823, compound

Participants

Reaction Steps

6-(5-aminomethyl-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (100 mg, 0.29 mmol), tetrahydro-pyran-4-carboxylic acid (57 mg, 0.44 mmol) and triethyl amine (0.12 mL, 0.88 mmol) are mixed in acetonitrile (3.0 mL). Then TBTU (113 mg, 0.35 mmol) is added and the mixture is stirred for 16 hrs. All the solvent is removed in vacuo and to the residue are added saturated NaHCO3 aqueous solution (5 mL), water (15 mL) and EtOAc (20 mL). The mixture is stirred for 10 min and the aqueous layer is separated and extracted with EtOAc (2×15 mL). The organic layers are combined and concentrated to give the crude 6-(5-{[(Tetrahydro-pyran-4-carbonyl)-amino]-methyl}-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester which is used in the next step directly.

Provenance & Evidence