HCID 178461965, compound → HCID 178463560, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)—N-[4-fluoro-2-(pyridin-2-ylamino)phenyl]-2-(9H-purin-6-ylamino)propionamide (130 mg, 0.332 mmol) in AcOH (1 mL) was heated for 2 h at 80° C. A second portion of (S)—N-[4-fluoro-2-(pyridin-2-ylamino)phenyl]-2-(9H-purin-6-ylamino)propionamide (136 mg, 0.347 mmol) in AcOH (5 mL) was heated for 2 h at 100° C. The two crude reaction mixtures were combined and the volatiles removed in vacuo. The resulting residue was partitioned between EtOAc and a saturated aqueous solution of NaHCO3. The organic layer was washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) then triturated in MeOH/diethyl ether to afford 182 as an off-white solid (66 mg, 26%). LCMS (Method K): RT 2.94 min [M+H]+ 375.0. 1H NMR (DMSO-d6, 400 MHz): δ 12.89 (1H, br s), 8.61 (1H, br s), 8.20-7.80 (4H, m), 7.79-7.67 (2H, m), 7.52-7.43 (1H, m), 7.20-7.08 (2H, m), 5.86 (1H, br s), 1.63 (3H, d, J=6.82 Hz)

Provenance & Evidence