N-(6-Methoxy-pyridin-3-yl)-2,2-dimethyl-propionamide synthesis

Yield:227180-19-0 100%

Reaction Conditions:

with triethylamine in dichloromethane; for 0.5 h;Cooling with ice;

Steps:

1a (1a) N-(6-methoxypyridin-3-yl)-2,2-dimethylpropionamide

Example 1 N-(4-{4-[3-(2-hydroxyethoxy)azetidin-1-yl]phenylamino}-6-methoxypyridin-3-yl)acetamide (1a) N-(6-methoxypyridin-3-yl)-2,2-dimethylpropionamide 6-Methoxypyridin-3-ylamine (13.2 g, 10.6 mmol) was dissolved in methylene chloride (130 mL), triethylamine (17.7 mL, 12.7 mmol) and pivaloyl chloride (13.6 mL, 11.1 mmol) were added under ice-cooling, and the mixture was stirred at the same temperature for 30 min. The reaction mixture was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title object compound as a pale-red powder (22.0 g, yield 100%). ¹H-NMR (CDCl₃, 400 MHz) δ: 1.32 (9H, s), 3.91 (3H, s), 6.71 (1H, d, J=8.8 Hz), 7.91 (1H, dd, J=8.8, 2.7 Hz), 7.33-7.40 (1H, br), 8.11 (1H, d, J=2.7 Hz).

References:

US2016/207883,2016,A1 Location in patent:Paragraph 0291-0293