Formaldehyde → N-[(3'-{[(3S)-3,4-dimethyl-1-piperazinyl]methyl}-6-fluoro-3-biphenylyl)methyl]-3-[(1-methyl-4-piperidinyl)methyl]benzamide

To a solution of N-[(3′-{[(3S)-3,4-dimethyl-1-piperazinyl]methyl}-6-fluoro-3-biphenylyl)methyl]-3-(4-piperidinylmethyl)benzamide (165 mg, 0.313 mmol) in 3 mL of MeOH, was added dropwise formaldehyde (37%, 101 mg, 1.25 mmol). After stirring for 30 minutes, sodium borohydride (24 mg, 0.63 mmol) was added. After stirring of the resulting mixture at rt for 12 hours, the solvent was removed under vacuum and the residue was purified by loading onto a 2 g aminopropyl SPE cartridge and eluting sequentially with DCM (3×5 mL), EtOAc (3×5 mL), and MeOH (3×5 mL). The DCM factions were combined and evaporated to give the title compound as a white solid (60 mg, 35%). LC/MS: m/z, 543 (M+H), 1.18 min.

1. stirringAfter stirring of the resulting mixture at rt for 12 hours
2. customthe solvent was removed under vacuum
3. customthe residue was purified
4. washeluting sequentially with DCM (3×5 mL), EtOAc (3×5 mL), and MeOH (3×5 mL)
5. customevaporated

ORD record

ord-d1cac5328ce8403f803c5eb9a385e122

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932247B2