4-Bromobenzoyl chloride → HCID 9850132, compound

Participants

Reaction Conditions

Reaction Steps

3-benzyl-2-(1-{[2-(dimethylamino)ethyl]amino}propyl)-3,5,6,7-tetrahydro-4H-cyclopenta[d]pyrimidin-4-one (1-4, 0.070 g, 0.20 mmol) was dissolved in CH2Cl2 (1.0 mL) and treated successively with 4-bromo-benzoylchloride (0.052 g, 0.24 mmol) and TEA (0.08 mL, 0.59 mmol). The reaction was stirred at 25° C. for 1 hour. The reaction was diluted with CH2Cl2 (10 mL), washed with 5% NaHCO3 and dried over MgSO4. The organics were concentrated under reduced pressure and subjected to preparative thin layer chromatography (SiO2, 5% MeOH/CH2Cl2) to provide N-[1-(3-benzyl-4-oxo-4,5,6,7-tetrahydro-3H-cyclopenta[d]pyrimidin-2-yl) propyl]-4-bromo-N-[2-(dimethylamino)ethyl]benzamide (1-5). 1H NMR (300 MHz, CDCl3) δ 7.53 (d, J=8.2 Hz, 2H), 7.31 (m, 5H), 12 (d, J=8.0 Hz, 2H), 5.98 (d, J=15.6 Hz, 1H), 5.85 (m, 1H), 4.99 (d, J=15.8 Hz, 1H), 3.36 (m, 2H), 2.90 (m, 4H), 2.10 (m, 4 H), 1.87 (s, 6H), 1.80 (m, 1H), 1.63 (m, 1H), 0.62 (m, 3H); MS 537.2 found, 537.5 required.

Provenance & Evidence