Hydrochloric Acid → N-[3-(3-{2-[(7-Amino-5,6,7,8-tetrahydro-2-naphthalenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2-(2-thienyl)acetamide

Participants

Reaction Steps

N-{5-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-methylphenyl}-2-(2-thienyl)acetamide (100 mg, 0.22 mmol), 3-(1-pyrrolidinylmethyl)aniline (78 mg, 0.44 mmol) and catalytic conc. HCl in iPrOH (4 mL) were heated in a microwave at 180° C. for 10 min. The reaction was concentrated and the residue was dissolved in DCM. The organic solution was washed with saturated NaHCO3 (aq) and water, dried over MgSO4 and concentrated onto silica gel. The crude material was purified by column chromatography. Fractions containing pure product were concentrated, taken up in MeOH and neutralized with MP-carbonate. The mixture was filtered and the filtered concentrated and triturated with DCM and hexanes to give the title compound (28 mg, 21%). 1H NMR (400 MHz, d6-DMSO) δ 9.62 (s, 1H), 9.50 (s, 1H), 8.80 (d, J=6.8 Hz, 1H), 8.50 (d, J=9.2 Hz, 1H), 8.21 (d, J=5.6 Hz, 1H), 7.73 (s, 1H), 7.68 (s, 1H), 7.63 (d, J=8.4 Hz, 1H), 7.45-7.41 (m, 1H), 7.36 (m, 1H), 7.32-7.28 (m, 2H), 7.16 (t, J=7.8 Hz, 1H), 7.11-7.07 (m, 1H), 6.98-6.95 (m, 2H), 6.87 (d, J=7.2 Hz, 1H), 6.50 (d, J=5.6 Hz, 1H), 3.91 (s, 2H), 3.50 (s, 2H), 2.39 (m, 4H), 2.26 (s, 3H), 1.65-1.64 (m, 4H) ppm. ES-LC/MS m/z=600 [M+H]+.

Provenance & Evidence