Trifluoromethanesulfonic acid → (R)-4-(2-(6-chloropyridin-3-ylamino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

Participants

Reaction Conditions

Reaction Steps

A brown solution of (R)-4-(2-(6-chloropyridin-3-ylamino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (125.0 mg, 0.168 mmol) and trifluoromethanesulfonic acid (0.15 mL, 1.689 mmol) in TFA (1.5 mL) was stirred at 75° C. for 1.5 h. The mixture was subsequently cooled to 25° C. and concentrated in vacuo. The residue was taken up in CH2Cl2 (50 mL), and the resulting solution was washed with saturated aqueous sodium bicarbonate (40 mL). The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (2×30 mL). All organic layers were then combined, dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0 to 10% MeOH/CH2Cl2) furnished (R)-4-(2-(6-chloropyridin-3-ylamino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (52.8 mg, 0.105 mmol, 62.4% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 12.16 (s, 1H), 8.88 (d, J=2.7 Hz, 1H), 8.74 (d, J=2.5 Hz, 1H), 8.48 (dd, J=8.7, 2.8 Hz, 1H), 8.35 (d, J=2.3 Hz, 1H), 7.45 (d, J=8.8 Hz, 1H), 3.59 (q, J=6.8 Hz, 1H), 3.09 (t, J=4.5 Hz, 4H), 2.86 (s, 3H), 2.56 (br. s., 2H), 2.46 (s, 3H), 2.41-2.45 (m, 2H), 1.36 (d, J=6.7 Hz, 3H). m/z (ESI, +ve) 504.1 (M+H)+.

Provenance & Evidence