Potassium Carbonate → HCID 59451896, compound

Participants

Reaction Steps

A mixture of N-(adamantanylmethyl)-2-(chloromethyl)imidazo[1,2-a]pyridine-5-carboxamide (HCl salt, 700 mg, 1.78 mmol), tert-butyl (3R)-pyrrolidin-3-ylcarbamate (496 mmol, 2.66 mmol) and potassium carbonate (615 mg, 4.45 mmol) in DMF (25 mL) is stirred at RT for 20 h. The reaction mixture is diluted with EtOAc and water. The organic layer is separated, and the aqueous layer is back extracted with EtOAc. The combined organic layers are washed with water and brine, dried over sodium sulfate, and concentrated. Purification of the residue by silica gel chromatography (10% MeOH, 1% NH4OH in DCM) affords the title compound. 1H-NMR (δ, ppm, CDCl3 as internal standard): 8.35 (s, 1H), 7.69 (d, J=8.7 Hz, 1H), 7.15 (dd, J=7.2 and 9.0 Hz, 1H), 7.08 (d, J=6.9 Hz, 1H), 6.33 (t, J=5.7 Hz, 1H), 4.16 (m, 1H), 3.85 (d, J=13.5 Hz, 1H), 3.78 (d, J=13.2 Hz, 1H), 3.2 (d, J=6.6 Hz, 2H), 2.91-2.64 (m, 2H), 2.44-2.21 (m, 2H), 2.02 (m, 3H), 1.77-1.58 (m, 15H), 1.41 (s, 9H).

Provenance & Evidence