Triethylamine → 6-(7-Azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-amine

Temperatur

80 °C

To a solution of 2-fluoro-4-methyl-5-nitropyridine (150 mg, 0.9608 mmol) in acetonitrile (5 mL) was added 7-azabicyclo[2.2.1]heptane hydrochloride (152.9 mg, 1.153 mmol) and Et3N (243.1 mg, 334.8 μL, 2.402 mmol). The reaction was heated at 80° C. for 16 h. The reaction was quenched with water (2 mL) and solvent was evaporated. The residue was dissolved in ethyl acetate (15 mL), washed with 1N HCl (10 mL), dried over MgSO4, filtered and concentrated to afford 6-(7-azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-amine (160 mg, 71% yield) as yellow solid which was used in next step without purification. 1H NMR (400.0 MHz, CDCl3) δ 8.96 (s, 1H), 6.37 (s, 1H), 4.59 (s, 2H), 2.59 (d, J=0.4 Hz, 3H), 1.83-1.80 (m, 4H), 1.61-1.54 (m, 4H).

1. customThe reaction was quenched with water (2 mL) and solvent
2. customwas evaporated
3. dissolutionThe residue was dissolved in ethyl acetate (15 mL)
4. washwashed with 1N HCl (10 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated

ORD-Eintrag

ord-0caa0e6f25eb4429adac578bda7b7bd3

Quelldatensatz

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08969382B2