Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 68181909, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(2-aminopyrimidin-4-yl)-6-(3-hydroxy-3-{5-[(oxan-2-yloxy)methyl]-1,2-oxazol-3-yl}but-1-yn-1-yl)-N,N-dimethylindazole-3-carboxamide (110 mg, 0.21 mmol) and pyridinium 4-methylbenzenesulfonate (5.18 mg, 0.2 mmol) in methanol (3 mL) was stirred at 60° C. for 1 hr, and then at RT for 3 days. Additional pyridinium 4-methylbenzenesulfonate was then added (20 mg, 0.8 mmol) and the reaction stirred at 55° C. for 1 hr. The reaction mixture was concentrated in vacuo and then saturated aqueous NaHCO3 (3 ml) solution was added. The product was extracted into DCM (5 ml×2). The combined organics were washed with brine and dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography (Isolute column). Elution with 3% methanol in DCM gave the title compound: 1H NMR (500 MHz, DMSO) delta 1.88 (3H, s), 3.12 (3H, s), 4.57 (2H, d, J 6.0), 5.67 (1H, t, J 6.1), 6.55 (1H, s), 6.66 (1H, s), 7.10 (1 H, d, J 5.5), 7.16 (2H, s), 7.43 (1H, d, J 8.4), 8.01 (1H, d, J 8.5), 8.35 (1H, d, J 5.5), 8.95 (1H, s); LC-MS m/z=+448.05 (M+H)+.

Provenance & Evidence