Pyridine → HCID 86647270, compound

Participants

Reaction Steps

4-Oxo-3-(2-oxo-butyl)-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide (Compound QQ-001) (25 mg, 0.1 mmol), MeONH2.HCl (13 mg, 0.15 mmol) were dissolved in an EtOH; Pyridine solution (1:1-0.5 ml). The reaction mixture was stirred for 16 hours before being concentrated in vacuo to give a crude residue which was redissolved in EtOAc (2 ml) and MeCN (2 mL). The solution was washed with aqueous 1M HCl and then dried (MgSO4), filtered and concentrated in vacuo. The crude product was redissolved in MeCN and passed through a silica plug. The filtrate was concentrated in vacuo to give the desired product as a green solid (17 mg, 61%). 1H NMR (400 MHz, d6-DMSO) δ ppm: 8.87 (1H, s), 8.86 (1H, s), 7.84 (2H, s), 7.71 (2H, s), 5.17 (2H, s), 5.04 (2H, s), 3.83 (2.85H, s), 3.73 (3H, s), 2.32 (2H, q, J=7.6 Hz), 2.19 (2H, q, J=7.2 Hz), 1.04 (3H, t, J=7.6 Hz), 0.99 (3H, t, J=7.2 Hz). m/z: 302.3 ((M+Na)+, 100), 280.4 (MH+).

Provenance & Evidence