Sodium Hydroxide → HCID 49783010, compound

Participants

Reaction Steps

Compound 21 (85 mg, 0.25 mmol) was refluxed in ethanol (10 mL) containing 1M NaOH (300 μl, 1.2 eq) for 5 hours. Additional base (300 μl) was added and the reaction continued for 2 hours before cooling to RT The reaction was quenched with 1N HCl (20 mL), the organic solvent removed and the remaining suspension filtered to give compound 22 (49 mg, 60%) as a white solid: MP 201-204° C. 1H NMR (500 MHz, DMSO-d6) δ 12.50 (s, 1H), 8.73 (s, 1H), 7.80 (d, J=8.7 Hz, 2H), 7.47 (d, J=8.7 Hz, 2H), 6.32 (d, J=7.6 Hz, 1H), 3.13 (t, J=12.1 Hz, 1H), 2.80 (t, J=11.8 Hz, 1H), 2.32 (q, J=7.4 Hz, 2H), 0.98 (t, J=7.4 Hz, 3H). Purity 94%. HRMS calculated for C16H21N3O4−H+ 318.1454. found (ESI(−), [M−H]) 318.1498.

Provenance & Evidence