Water → HCID 178522746, compound

Participants

Reaction Conditions

Reaction Steps

NaN3 (65 mg, 0.48 mmol) and NH4Cl (26 mg, 0.48 mmol) are added to a solution of 2-(2-cyano-ethyl)-pyrazolo[1,5-a]pyridine-4-carboxylic acid (adamantan-1-ylmethyl)-amide (58 mg, 0.16 mmol) in DMSO at rt. The mixture is heated to 130° C. for 6 h. Additional NaN3 (65 mg, 0.48 mmol) is added, and the mixture is heated for 14 h. The mixture is cooled to rt. H2O is added and pH is adjusted to about 7. The aqueous layer is extracted with EtOAc (3×15 mL), dried over Na2SO4 and the solvent is removed to dryness. The crude product is purified by PTLC (eluted with 2% MeOH in DCM) to give the title compound. 1H NMR (CDCl3): 8.49-8.47 (d, 1H), 7.52-7.50 (d, 1H), 6.79-6.69 (t, 1H), 6.69 (s, 1H), 6.40 (b, 1H), 3.44-3.41 (m, 2H), 3.31-3.29 (m, 2H), 3.20-3.19 (m, 2H), 2.00 (b, 3H), 1.74-1.60 (m, 12H). LC-MS m/z (M+H+): 406.07.

Provenance & Evidence