Dichloromethane → 3,5-Dichloro-N-(4-fluorobenzyl)-N-(4-((4-fluorobenzylamino)methyl)benzyl)-2-hydroxybenzenesulfonamide

To a solution of N-(4-(aminomethyl)benzyl)-3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide (235 mg, 0.50 mmol) in a mixed solvent (10 mL of CH2Cl2 and 2 mL of i-propanol) at rt was added 4-fluorobenzaldehyde (62 mg, 0.50 mmol). The reaction mixture was stirred at rt overnight. The next morning, sodium borohydride (37 mg, 1.00 mmol) was added, and the mixture was stirred at rt for 2 h. The reaction mixture was quenched by adding 3 mL of MeOH and 3 ml of saturated aq NaHCO3. The reaction mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were dried, concentrated and purified by prep HPLC to give the title compound (164 mg, 57%) as a white solid. MS (ESI): 577.0 (M+H)+.

1. stirringthe mixture was stirred at rt for 2 h
2. customThe reaction mixture was quenched
3. additionby adding 3 mL of MeOH and 3 ml of saturated aq NaHCO3
4. extractionThe reaction mixture was extracted with EtOAc (3×50 mL)
5. customThe combined organic extracts were dried
6. concentrationconcentrated
7. custompurified by prep HPLC

ORD record

ord-d411041a04ed4ca0bb7f576347a039da

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501992B2