Methanesulfonic Acid → HCID 59548172, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)-N,N-dimethylpiperazine-1-carboxamide (0.3555 g, 0.482 mmol) in TFA (1.859 mL, 24.12 mmol) was treated with methanesulfonic acid (0.031 mL, 0.482 mmol) and the solution was heated at 85° C. overnight. After cooling, the residue was carefully concentrated and diluted with 5% MeOH/DCM w/NH3. The solution was concentrated with SiO2 and chromatographed through a Redi-Sep pre-packed silica gel column (pure DCM to 10% MeOH in DCM) to give 4-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)-N,N-dimethylpiperazine-1-carboxamide (88 mg, 0.177 mmol, 36.7% yield). 1H NMR (400 MHz, d6-DMSO) δ 12.04 (s, 1H); 8.92 (br. s., 1H); 8.45 (s, 1H); 8.40 (br. s., 1H); 8.33 (d, J=11.35 Hz, 1H); 7.96 (br. s., 1H); 7.87 (br. s., 1H); 4.40 (br. s., 2H); 3.95 (s, 3H); 3.64 (d, J=14.87 Hz, 2H); 3.25-3.35 (m, 2H); 2.88-3.15 (m, 4H); 2.78 (s, 6H); 2.44 (s, 3H). m/z (ESI, +ve ion) 497.1 (M+H)+.

Provenance & Evidence