Triethylamine → HCID 59569572, compound

Participants

Reaction Steps

The title compound was prepared according to general procedure C described in connection with Scheme 5. To a solution of 1-(t-butoxycarbonyl)-3-(cyclopropylmethyl)pyrrolidine-3-carboxylic acid IIIb (300 mg, 1.11 mmol) in 16 mL of CH2Cl2 was added thionyl chloride (0.24 mL, 3.34 mmol) and two drops of DMF. The mixture was stirred for ˜1-2 h at room temperature. After removal of solvent, the residue was redissolved in CH2Cl2 (13 mL), followed by the addition of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride (IVa) (320 mg, 1.16 mmol) and triethyl amine (0.78 mL, 5.5 mmol). LC-MS analysis indicated the completion of the reaction after one hour stirring at RT. The mixture was washed with water (×2) and brine (×3). After concentration of solvent, the crude residue was purified by flash chromatography on silica gel to give 300 mg (60% yield) of the desired product. MS (ESI) m/z: Calculated for C23H30F3N3O3: 453.2. found: 453.7 (M+Na)+.

Provenance & Evidence