Trifluoroacetic acid → N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)benzo[d]thiazol-5-amine

Participants

Reaction Conditions

Reaction Steps

A microwave vial (5 mL) was charged with N-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)benzo[d]thiazol-5-amine (45.0 mg, 0.060 mmol) in trifluoroacetic acid (Aldrich, St. Louis, Mo.) (1.50 mL, 20.19 mmol). The mixture was heated in a microwave at 120° C. for 45 min, and then the solvent was removed in vacuo. The residue was purified with reverse phase preperative HPLC using a Phenomenex Gemini columb, 5 micron, C18, 100 Å, 150×30 mm (eluting with 10% to 55% MeCN/water with 0.1% TFA over 30 minutes with a total flow rate of 45 mL/min) to give N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)benzo[d]thiazol-5-amine (16.0 mg, 0.031 mmol, 52.3% yield) as a yellow solid after solvent removal and neutralization. 1H NMR (400 MHz, d6-DMSO) δ 12.23 (1H, s); 9.35 (1H, s); 8.90 (1H, d, J=1.8 Hz); 8.76 (1H, d, J=2.0 Hz); 8.34 (1H, d, J=2.0 Hz); 8.06 (1H, d, J=8.8 Hz); 7.91 (1H, br. s.); 7.72-7.86 (2H, m); 3.53 (2H, s); 3.12 (4H, d, J=4.1 Hz); 2.87 (3H, s); 2.48 (7H, br. s.). m/z (ESI, +ve ion) 512 (M+H)+.

Provenance & Evidence