2-Bromoacetamide → HCID 71244765, compound

Participants

Reaction Steps

A mixture of (R)-2-(2,5-dimethylphenyl)-6-(5-isopropyl-2-methylphenyl)-4-(2-methylpiperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (43 mg, 0.053 mmol), 2-bromoacetamide (14.6 mg, 0.106 mmol) and DIEA (0.074 mL, 0.424 mmol) in DCM (2 mL) was stirred at rt for 16 h. The reaction was then diluted with EtOAc, and washed successively with sat aq NaHCO3, and brine. The organic layer was then dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by HPLC(C18, 15-85% acetonitrile in H2O with 0.1% NH4OH) to provide (R)-2-(4-(2-(2,5-dimethylphenyl)-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)acetamide. 1H NMR (400 MHz, DMSO-d6, at 120° C.) δ ppm 7.58 (s, 1 H) 7.08-7.18 (m, 5 H) 6.99 (d, J=1.64 Hz, 1 H) 6.87 (dd, J=7.71, 1.64 Hz, 1 H) 4.01-4.09 (m, 1 H) 3.89-4.01 (m, 2 H) 3.48-3.58 (m, 1 H) 3.37-3.47 (m, 1 H) 2.97 (t, J=5.87 Hz, 2 H) 2.81-2.90 (m, 3 H) 2.78 (d, J=10.36 Hz, 1 H) 2.61 (dd, J=11.62, 1.77 Hz, 1 H) 2.47 (s, 3 H) 2.40 (dd, J=11.31, 3.35 Hz, 1 H) 2.23-2.34 (m, 4 H) 2.20 (s, 3 H) 1.28 (d, J=6.44 Hz, 3 H) 1.19 (dd, J=6.95, 1.52 Hz, 6 H); MS (ESI+) m/z 527.4 (M+H)+.

Provenance & Evidence