Dimethylamine → HCID 178483679, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of cis-toluene-4-sulfonic acid 3-[8-amino-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclobutylmethyl ester (30.0 mg, 0.0555 mmol), 2 M of dimethylamine in MeOH (2 mL) and THF (5 mL, 0.06 mol) was heated to 60° C. overnight in a sealed tube. The material was concentrated in vacuo, redissolved in minimal MeOH/DCM, and loaded onto a prep TLC plate, eluting with 6% (7N NH3 in MeOH)/DCM. The band containing the pure product was collected, and the product was filtered off using 1:1 MeOH/DCM. The filtrate was concentrated in vacuo, and hexanes was added. The mixture was sonicated until a white precipitate crashed out. The solid was filtered off, washing several times with hexanes, to afford the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ=2.23 (s, 6H), 2.26-2.33 (m, 2H), 2.42 (d, J=6.3 Hz, 2H), 2.57-2.70 (m, 3H), 3.60-3.71 (m, 1H), 5.03 (s, 2H), 7.03-7.17 (m, 7H), 7.34-7.41 (m, 2H), 7.61-7.65 (m, 2H). MS (ES+): m/z 414.19 (100) [MH+]. HPLC: tR=1.98 min (ZQ3, polar—5 min).

Provenance & Evidence