Hydrochloric Acid → 5-({[(2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-[4-(4,5-dihydro-1H-imidazol-2-yl)benzyl]furan-3-carboxamide

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Reaction Steps

5-({[(2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (51 mg, 0.14 mmol) was dissolved in DCE (0.5 mL) and CDI (34 mg, 0.21 mmol) was added. The mixture was stirred until acid activation was complete. 1-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methanamine.HCl (180 mg, 0.42 mmol) and DIPEA (0.22 mL, 1.26 mmol) were sonicated in DMF (3 mL) for 15 min, 0.25 mL of activated acid solution was added to 0.5 mL of amine solution and the reaction was diluted with DMF (1.5 mL) and stirred at ambient temperature for 18 h. The reaction was concentrated, dissolved in DCM and washed with water (3×1.5 mL) and saturated brine (1 mL)). The organic layer was dried over MgSO4, shaken with Ambersep and PL-MIA resins, and solvents were removed in vacuo. A portion of the crude product was purified using prep method C.

Provenance & Evidence