1-Adamantaneacetic acid → 4-(2-Adamantan-1-ylacetylamino)pyrazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A 1.0 M solution of triethylamine in toluene (0.3 mL) is added to a solution of 1-adamantaneacetic acid (14 mg, 80 μmol) and 4-aminopyrazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester (12 mg, 60 μmol) in DMF (0.3 mL) under N2. A solution of 2-chloro-1,3-dimethylimidazolinium chloride (20 mg, 120 μmol) in ACN (0.3 mL) is added. The reaction vessel is sealed and the mixture is warmed to 50° C. for 2 h. The mixture is cooled to rt. 50% Sat. aq. NaHCO3 (2 mL) is added. The solution is extracted with Et OAc (2×1 mL). The combined organics are concentrated. Purification by preparative thin layer chromatography (2:1 hexanes:EtOAc) affords the title compound as a light tan solid. 1H NMR (400 MHz, CDCl3) δ: 8.32 (d, 1H), 8.05 (d, 1H), 7.15 (s, 1H), 7.05 (s, 1H), 6.91 (t, 1H), 4.59 (q, 2H), 2.21 (s, 2H), 1.98-2.06 (m, 3H), 1.56-1.78 (m, 12H), 1.46 (t, 3H). LC-MS m/z (M+H+): 382.10.

Provenance & Evidence