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

5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (60 mg, 0.14 mmol)), EDCI (40 mg, 0.21 mmol) and HOAt (28 mg, 0.21 mmol) were dissolved in DMF (1 mL) and the mixture was stirred until acid activation was complete. 2-[4-(4,5-Dihydro-1H-imidazol-2-yl)phenyl]ethanamine.HCl (114 mg, 0.50 mmol) and DIPEA (0.174 mL, 1.00 mmol) were sonicated in 1 mL DMF for 5 min. The activated acid solution was added to 0.25 mL of amine solution and the reaction was stirred at ambient temperature for 3 h. The reaction was diluted with DCM (15 mL) and washed with saturated aqueous NH4Cl (2×3 mL). The organic layer was dried over MgSO4 and solvents were removed in vacuo. A portion of the crude product was purified using prep method C.

1. stirringthe reaction was stirred at ambient temperature for 3 h
2. washwashed with saturated aqueous NH4Cl (2×3 mL)
3. dry with materialThe organic layer was dried over MgSO4 and solvents
4. customwere removed in vacuo
5. customA portion of the crude product was purified

ORD record

ord-6eb4a9fea7814e52a177feed56adc814

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08623859B2