Hydrochloric Acid → HCID 89650338, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 4-[[2-(ethylcarbamoylamino)-5-(3-pyridylcarbamoyl)-4-pyridyl]amino]benzoate (35 mg, 0.07 mmol) was suspended in acetonitrile (3 mL) and water (3 mL) and treated with NaOH (1 mL, 1 M). The mixture was heated to 40° C. for 40 minutes. The mixture was adjusted to pH ˜6 by addition of dilute aqueous HCl. The mixture was then freeze-dried. The crude product was dissolved in DMSO/water and purified by reverse phase chromatography (12 g Reveleris C18 cartridge, eluting with 0-100% acetonitrile in 0.1% aqueous formic acid). Compound 16 was isolated as a white solid (23 mg, 68%). 1H NMR (400 MHz, DMSO-d6): δ 10.53 (s, 1H), 10.04 (s, 1H), 9.24 (s, 1H), 8.86 (d, J=2.1 Hz, 1H), 8.64 (s, 1H), 8.32 (dd, J=4.7, 1.5 Hz, 1H), 8.12 (ddd, J=8.4, 2.5, 1.5 Hz, 1H), 7.93 (d. J=8.7 Hz, 2H), 7.87 (s, 1H), 7.51 (s, 1H), 7.40 (ddd, J=8.4, 4.7, 0.6 Hz, 1H), 7.36 (d. J=8.8 Hz, 2H), 3.20-3.12 (m, 2H), 1.07 (t, J=7.2 Hz, 3H). [M+H]+ m/z=421.14.

Provenance & Evidence