3-Aminopyridine → HCID 21904427, compound

To a solution of N-Boc-piperidin-3-yl-formaldehyde 3 (0.89 g, 4.16 mmol) in 3 mL of dry methanol and 3 mL of trimethylorthoformate was added 3-aminopyridine (0.39 g, 1 eq.), and the mixture was stirred at room temperature for 1.5 hours. NaBH3CN (95%, 0.29 g, 1.05 eq.) was introduced in one portion, and the mixture was stirred at room temperature overnight. The mixture was quenched with 10 mL of aqueous potassium carbonate (sat.), then extracted with ethyl acetate (3×30 mL). The extracts were combined and washed with aqueous NaHCO3 (sat., 2×10 mL), brine (20 mL), and dried over anhydrous sodium sulfate. After the solvent was removed, the remaining oily residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate) to afford N-(1-Boc-piperidin-3-ylmethyl)-N-(pyridin-3-yl) amine 17 as a white solid (0.91 g, 75%). LRMS 292.

1. stirringthe mixture was stirred at room temperature overnight
2. customThe mixture was quenched with 10 mL of aqueous potassium carbonate (sat.)
3. extractionextracted with ethyl acetate (3×30 mL)
4. washwashed with aqueous NaHCO3 (sat., 2×10 mL), brine (20 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. customAfter the solvent was removed
7. customthe remaining oily residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate)

ORD record

ord-843b8097fbec47cc89a9c3ac35e40636

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06677332B1