Acetic Acid → HCID 178463562, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)—N-[4-fluoro-2-(6-fluoropyridin-3-ylamino)phenyl]-2-(9H-purin-6-ylamino)propionamide (255 mg, 0.62 mmol) in AcOH (10 mL) was heated at 100° C. for 24 h. After cooling to RT, the volatiles were removed under reduced pressure and the residue was partitioned between EtOAc and a saturated aqueous solution of NaHCO3. The aqueous phase was extracted with EtOAc and the combined organic fractions washed with water, followed by brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-20% 2M NH3/MeOH in DCM) to afford 382 as a pink solid (38 mg, 16%). LCMS (Method K): RT 2.40 min [M+H]+ 391.0. 1H NMR (DMSO-d6+TFA-D, 400 MHz, 80° C.): δ 8.58-8.49 (2H, m), 7.82 (1H, d, J=2.96 Hz), 7.75 (1H, dd, J=8.81, 4.70 Hz), 7.51 (1H, dd, J=9.59, 2.99 Hz), 7.21-7.07 (2H, m), 6.40 (1H, d, J=9.60 Hz), 5.86 (1H, br d), 1.79 (3H, d, J=6.82 Hz)

Provenance & Evidence