HCID 67092227, compound → HCID 67092285, compound

Participants

Reaction Conditions

Reaction Steps

To a flask charged with NH4CO2H (6.2 g, 98.4 mmol) was added MeOH (50 mL) and stirred to a solution, followed by addition of a solution of 4-[1-[1-(diphenylmethyl)azetidin-3-yl]-5-(4-fluorobenzyl)-1H-pyrazol-3-yl]pyridine (2.3 g, 4.85 mmol) in EtOAc (50 mL), and the mixture stirred to a homogenous solution. This was added to a second flask containing 10% Pd/C (0.84 g) in MeOH (100 mL) under N2, and the reaction mixture was heated to 57° C. under N2 for 5 hours. The mixture was cooled to room temperature and the solids removed by filtration through a GF/F filter set. The filtrate was concentrated and diluted with water (50 mL) and then saturated with NaOH. The emulsion was then extracted with CH2Cl2 (3×100 mL) followed by Et2O (4×100 mL). The combined organic layers were dried over MgSO4, filtered and concentrated. The crude residue was purified by flash chromatography (90:10:1 CH2Cl2/MeOH/NH4OH) to yield the title compound as a white solid, 0.892 g, 60%. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 8.61 (d, 2 H), 7.69 (d, 2 H), 7.06-7.14 (m, 2 H), 6.95-7.05 (m, 2 H), 6.42 (s, 1 H), 4.91-5.08 (m, 1 H), 4.29 (t, 2 H), 3.98 (s, 2 H), 3.61 (t, 2 H); m/z (APCI+) for C18H17N4F 309.2 (M+H)+.

Provenance & Evidence