4-Methylmorpholine → HCID 178463565, compound

Participants

Reaction Steps

A mixture of [(S)-1-(1-azetidin-3-yl-6-fluoro-1H-benzoimidazol-2-yl)ethyl]-(9H-purin-6-yl)amine (75 mg, 0.21 mmol) dimethylaminoacetic acid (25 mg. 0.23 mmol), 4-methylmorpholine (70 μL, 0.64 mmol) and HATU (93 mg, 0.24 mmol) in DMF (2 mL) was stirred at RT for 4 h. The crude mixture was partitioned between EtOAc and a saturated aqueous solution of NaHCO3. The aqueous phase was further extracted with EtOAc and the combined organic fractions washed with water, followed by brine, dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2N NH3/MeOH in DCM) followed by reverse phase HPLC (Phenomenex Gemini 5 μm C18 on a gradient 5-60%, 0.1% NH4OH in acetonitrile/water) to afford 381 as a white solid (20 mg, 22%). LCMS (Method K): RT 1.86 min [M+H]+ 438.1. 1H NMR (DMSO-d6, 400 MHz): δ 8.30-7.92 (3H, m), 7.71-7.63 (1H, m), 7.45-7.34 (1H, m), 7.11 (1H, t, J=9.36 Hz), 5.93-5.58 (2H, m), 4.82-4.69 (1H, m), 4.67-4.56 (1H, m), 4.49-4.34 (1H, m), 4.25-4.26 (1H, m), 3.14 (1H, d, J=14.18 Hz), 2.89 (1H, dd, J=14.18, 3.84 Hz), 2.23 (3H, s), 2.22 (3H, s), 1.67 (3H, d, J=6.66 Hz)

Provenance & Evidence