HCID 66610744, compound → HCID 59548204, compound

Participants

Reaction Steps

A solution of N-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl)-2-methylbenzo[d]oxazol-5-amine (0.116 g, 0.202 mmol) in TFA (8.0 mL) (Aldrich) was heated at 80° C. overnight. The TFA was removed in vacuo. The crude product was dissolved in 4 mL of DMSO and was purified by reversed phase chromatography (Gilson; 10-90% CH3CN in water with TFA additive: 0.1% v/v in each solvent). The fractions were combined and the CH3CN was removed. DCM was added and the whole was washed with a saturated solution of NaHCO3 (1×), brine (1×), dried over MgSO4, filtered and concentrated. The compound and impurities had co-eluted. The material was purified by flash column chromatography using an ISCO Combiflash Companion (4 g column; 1-10% MeOH in DCM over 40 minutes). The compound and impurities co-eluted. The crude product was dissolved in 4 mL of DMSO. Purification by reversed phase chromatography (Gilson; 10-90% CH3CN in water with NH4OH additive: 0.1% v/v in each solvent) followed by drying in a Genevac Series II System gave N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl)-2-methylbenzo[d]oxazol-5-amine (1.079 mg, 3.24 μmol, 1.6% yield) as a yellow amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 12.04 (s, 1H); 8.79 (dd, J=7.7, 2.1 Hz, 1H); 8.37 (dd, J=4.7, 2.0 Hz, 1H); 8.33 (d, J=2.0 Hz, 1H); 7.86 (q, J=3.2 Hz, 1H); 7.70-7.77 (m, 1H); 7.62-7.68 (m, 1H); 7.54-7.60 (m, 1H); 6.91 (dd, J=7.8, 4.7 Hz, 1H); 2.60 (s, 3H); 2.45 (s, 4H). m/z (ESI, +ve ion) 334.1 (M+H)+.

Provenance & Evidence