Ammonium formate → HCID 59353051, compound

Participants

Reaction Steps

To a mixture of 2-(benzyloxy)-N-(3-{[(3-{[2-(3-hydroxypropyl)-5-methoxyphenyl]amino}quinoxalin-2-yl)amino]sulfonyl}phenyl)acetamide (69 mg; 0.1 mmol; 1 eq) in EtOH (12 mL) are added ammonium formate (69.3 mg; 1.1 mmol; 10 eq) and palladium on charcoal (10 mg, 10%). The reaction mixture is stirred at reflux for 2 h. The catalyst is filtered through celite, washed with EtOH and the filtrate is concentrated under reduced pressure to give a yellow residue. It is suspended in EtOH (2 mL), sonicated, filtered off and washed with EtOH (400 μL). The solid is dried in vacuo to give 41 mg (70%) of the title compound as a yellow solid 1H NMR (DMSO-d6) δ 12.53 (br s, 1H), 10.00 (s, 1H), 8.73 (s, 1H), 8.45 (s, 1H), 8.19 (br s, 1H), 7.99-7.91 (m, 2H), 7.75 (d, J=7.4 Hz, 1H), 7.57-7.48 (m, 2H), 7.42-7.32 (m, 2H), 7.09 (d, J=8.3 Hz, 1H), 6.68-6.61 (m, 1H), 5.75-5.62 (m, 1H), 4.45-4.30 (m, 1H), 4.00 (s, 2H), 3.70 (s, 3H), 3.28-3.15 (m, 4H), 1.58-1.45 (m, 2H). HPLC (max plot) 99%; Rt 3.71 min. UPLC/MS (ES−) 538.2, (ES−) 536.3.

Provenance & Evidence