1,1'-Carbonyldiimidazole → HCID 71002255, compound

Participants

Reaction Steps

1-{4-[4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]phenyl}methanamine (58 mg, 1.8 mmol) was dissolved in dichloromethane (1.8 mL) and treated with carbonyldiimidazole (0.15 g, 0.93 mmol, 5 equiv). The mixture was stirred at ambient temperatures for 2 hours and then treated with ethyl aminoacetate hydrochloride (0.26 g, 1.8 mmol, 10 equiv). The mixture was stirred until complete, diluted with dichloromethane (30 mL) and washed with sodium bicarbonate (2×30 mL, aqueous saturated). The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (85:15 to 35:65; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid) to afford the titled compound: 1H-NMR (400 MHz, CDCl3) δ 7.53-7.40 (6H, m); 4.55 (2H, dd, J=6.9, 3.8 Hz); 4.49 (2H, m); 4.25-4.17 (2H, m); 4.02 (2H, s); 1.47-1.38 (1H, m); 1.27 (3H, t, J=6.6 Hz); 0.71-0.66 (2H, m); 0.54-0.49 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 442.1660 [(M+H)+; calculated for C22H25ClN5O3: 442.1640].

Provenance & Evidence