Acetic Acid → HCID 86692728, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(2-((4-iodobenzyl)amino)ethyl)benzenesulfonamide (208 mg, 0.50 mmol), AcOH (0.05 mL) and tert-butyl 2-(2-formyl-1H-imidazol-1-yl)acetate (0.105 mg, 0.50 mmol) in DCE (10 mL) at 0° C. was added NaBH(OAc)3 (0.30 g, 1.5 mmol). The reaction mixture was stirred at 0° C. for 30 minutes and at room temperature for overnight and decomposed with water. The reaction mixture was extracted with DCM. The organic layer was dried and concentrated under reduced pressure. The residue was purified by biotage over silica gel eluting with DCM to 10% MeOH in DCM to afford tert-butyl 2-(2-(((4-iodobenzyl)(4-sulfamoylphenethyl)amino)methyl)-1H-imidazol-1-yl)acetate (27.9 mg, 91%). 1H NMR (400 MHz, CDCl3) 7.78 (d, J=8.4 Hz, 2H), 7.65 (d, J=8.4 Hz, 2H), 7.15 (d, J=8.4 Hz, 2H), 7.03 (d, J=8.0 Hz, 2H), 6.95 (d, J=1.2 Hz, 1H), 6.79 (d, J=0.8 Hz, 1H), 4.78 (s, 2H), 4.31 (s, 2H), 3.62 (s, 2H), 3.57 (s, 2H), 2.82-2.68 (m, 4H), 1.39 (s, 9H); MS (ESI), 611.1 (M+H)−.

Provenance & Evidence