Potassium Carbonate → HCID 42599841, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloro-N-methyl-acetamide (0.027 ml) in DMF (1 ml) was added to a stirred mixture of 3-(1,3-benzoxazol-2-yl)-5-[3-(methoxymethyl)-1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine (100 mg) and potassium carbonate (68 mg) in DMF (5 ml) at 25° C. under argon. The resulting solution was heated at 75° C. overnight. The DMF was evaporated and the residue was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (5 microns silica, 30 mm diameter, 150 mm length) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions were evaporated to afford 2-[4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]-3-(methoxymethyl)pyrazol-1-yl]-1-piperidyl]-N-methyl-acetamide (53.0 mg) as a solid. NMR Spectrum: (DMSOd6) 1.98-2.06 (m, 2H), 2.09 (dd, 1H), 2.14 (dd, 1H), 2.22-2.31 (m, 2H), 2.64 (d, 3H), 2.86-2.93 (m, 2H), 2.95 (s, 2H), 3.41 (s, 3H), 4.11-4.19 (m, 1H), 4.41 (s, 2H), 7.41-7.48 (m, 2H), 7.66 (bs, 2H), 7.75 (q, 1H), 7.78 (dd, 1H), 7.84 (dd, 1H), 8.19 (s, 1H), 8.43 (d, 1H), 8.50 (d, 1H); Mass spectrum: M+H+ 476.

Provenance & Evidence