Acetic Acid → HCID 89544943, compound

Participants

Reaction Steps

A mixture of [3-((R)-1-Amino-propyl)-6-chloro-2-fluoro-phenyl]-(6-amino-pyridin-3-yl)-methanone (100 mg, 0.29 mmol), paraformaldehyde (26 mg, 0.87 mmol), sodium triacetoxyborohydride (92 mg, 0.44 mmol) and acetic acid (67 μL, 1.16 mmol) in DCM (0.5 mL) was stirred for 18 h. Chromatographic analysis showed mainly bis-addition peaks, but a small peak for product. Further DCM (5 mL) and water (5 mL) were added and the mixture was made basic with a few drops of 5M NaOH. Separated and aqueous extracted with further DCM (5 mL). The combined organic phase was washed with brine (4 mL), dried (MgSO4), filtered and concentrated. Purified by prep LCMS (basic 3) and concentrated to give (6-Amino-pyridin-3-yl)-[6-chloro-2-fluoro-3-((R)-1-methylamino-propyl)-phenyl]-methanone (3 mg). Dissolved in d6-DMSO (160 uL) and concentration determined by NMR—53 mM. Used as solution for assays. [MH]+ 322.

Provenance & Evidence