Aniline → HCID 68928484, compound

Participants

Reaction Steps

To a solution of toluene-4-sulfonic acid 4-[8-amino-1-(3-benzyloxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexylmethyl ester (29 mg, 0.05 mmol) in DMF (0.5 ml) was added aniline (23 μl, 0.25 mmol). The reaction was irradiated in the microwave (200 W, 150° C., 10 m), then evaporated to dryness. The crude reaction product was dissolved in MeOH (2 ml) and added to a pre-wetted MCX cartridge (6 ml/500 mg). The cartridge was washed with MeOH (10 ml) and the product was then eluted using 1% NH3 in MeOH (15 ml). The product was further purified using mass-directed HPLC, to give 1-(3-benzyloxy-phenyl)-3-(4-phenylaminomethyl-cyclohexyl)-imidazo[1,5-a]pyrazin-8-ylamine formic acid salt (7.8 mg, 31%) as an off-white solid: 1H NMR (400 MHz, CD3OD) δ 8.25 (s, 1H), 7.60 (d, 1H, J=5.5 Hz), 7.48-7.41 (m, 3H), 7.36 (t, 2H, J=7.3 Hz), 7.33-7.27 (m, 1H), 7.25-7.22 (m, 1H), 7.18 (d, 1H, J=7.4 Hz), 7.13 (dd, 1H, J=5.5 Hz, 2.3 Hz), 7.08 (t, 2H, J=7.8 Hz), 6.97 (d, 1H, J=5.5 Hz), 6.63 (d, 2H, J=7.4 Hz), 6.58 (t, 1H, J=7.4 Hz), 5.16 (s, 2H), 3.12 (m, 1H), 3.00 (d, 2H, J=6.7 Hz), 2.06 (br. d, 4H, J=11.7 Hz), 1.88-1.70 (m, 3H), 1.30-1.22 (m, 2H), 3H not observed (NH2 and NH); MS (ES+) m/z 504.24 [MH+] at Rt 3.47 min.

Provenance & Evidence