2-Methoxy-3-pyridinemethanamine

Synthesis of 3-aminomethyl-2-methoxypyridine EPO A round bottom flask was charged with 0.44g (3.23mM) of 2-methoxy-3-pyridine carboxaldehyde (24), 1.24g (16.15mM) of ammonium acetate, and 0.61g (19.69mM) of sodium cyanoborohydride. The flask was then flushed with argon, and then 5OmL of dry MeOH was added by syringe. The reaction was stirred for 2 days, at which point the MeOH was evaporated off. 25mL of water was added, and the mixture was brought to pH 2 with cone. HCl. This was extracted twice with EtOAc to remove the alcohol side product. The mixture was brought to pH 10 using sodium hydroxide pellets, saturated with NaCl, and extracted twice with DCM and once with EtOAc. The combined organics were dried and evaporated to give 0.31g (69percent) of 3-aminomethyl-2-methoxypyπdine (25).General procedure: To a solution of 16 (2.1 g, 4.7 mmol) in DMI (20 mL), 2-(trifluoromethoxy)benzylamine (1.8 g, 9.4 mmol) was added at 0 °C andstirred at room temperature for 1 h. The reaction mixture was pouredinto H2O, collected by vaccum filtration and chromatographed on silicagel with elution using (n-hexane-EtOAc) (8:2 to 7:3) to give a colorlesssolid. To a suspension of obtained product in CH2Cl2 (30 mL), TFA(14 mL) was added at 0 °C and stirred at room temperature for 1 h. Thereaction mixture was concentrated in vascuo. To the residue, saturatedaqueous NaHCO3 was added and the precipitate was washed with H2Oand n-hexane to give 3 (1.7 g, 76percent) as a colorless solid. .General procedure: To a solution of compound 3w (0.70g, 2.1mmol) in THF (10ml) was added phenyltrimethylammonium tribromide (0.79g, 2.1mmol). The reaction mixture was stirred at room temperature for 12h. Water (50mL) was added and the mixture was extracted with ethyl acetate (10mL×3), the combined organic phase was washed with water (30mL×2), dried over anhydrous Na2SO4 and concentrated to afford the intermediate 4w. To a solution of different pyridin-3-ylmethanamine derivatives (2.1mmol) in acetone (10ml) was added Et3N (0.43g, 4.2mmol). The reaction mixture was stirred for 5min and was added CS2 (0.24g, 3.15mmol) to continuously stir for 30min. The intermediate 4w were added respectively and this mixture was stirred at room temperature for 4h. Water (50mL) was added and the mixture was extracted with ethyl acetate (10mL×3), the combined organic phase was washed with brine (30mL×2), dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to provide the product.Synthesis of Synthesis of A round bottom flask was charged with 0.44g (3.23mM) of 2-methoxy-3-pyridine carboxaldehyde (24), 1.24g (16.15mM) of ammonium acetate, and 0.61g (19.69mM) of sodium cyanoborohydride. The flask was then flushed with argon, and then 5OmL of dry MeOH was added by syringe. The reaction was stirred for 2 days, at which point the MeOH was evaporated off. 25mL of water was added, and the mixture was brought to pH 2 with cone. HCl. This was extracted twice with EtOAc to remove the alcohol side product. The mixture was brought to pH 10 using sodium hydroxide pellets, saturated with NaCl, and extracted twice with DCM and once with EtOAc. The combined organics were dried and evaporated to give 0.31g (69percent) of 3-aminomethyl-2-methoxypypidine (25).

Molecular Weight:138.17
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:138.079312947
Monoisotopic Mass:138.079312947
Topological Polar Surface Area:48.1
Heavy Atom Count:10
Complexity:97.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes