Triethylamine → Methyl 3-[2-({4-[(2-methoxypyridin-4-yl)oxy]-2-(methylamino)phenyl}amino)-2-oxoethoxy]benzoate

Pivaloyl chloride (1.74 mL, 14.2 mmol) was added dropwise to a solution of [3-(methoxycarbonyl)phenoxy]acetic acid produced in Example (1c) (3.27 g, 15.6 mmol) and triethylamine (1.97 mL, 14.2 mmol) in dichloromethane (40 mL) in a nitrogen atmosphere at 0° C. After one hour, a solution of 4-[(2-methoxypyridin-4-yl)oxy]-N2-methylbenzene-1,2-diamine produced in Example (16d) (3.46 g, 14.2 mmol) and triethylamine (1.97 mL, 14.2 mmol) in dichloromethane (40 mL) was added dropwise at 0° C., and the mixture was stirred at room temperature for two hours. The reaction mixture was concentrated under reduced pressure. Then, the residue was purified by silica gel chromatography (ethyl acetate) to obtain the title compound (4.81 g, 78%) as a pale brown oil.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. customThen, the residue was purified by silica gel chromatography (ethyl acetate)

ORD record

ord-8c78410083224c04b8f3f00b1be56ed0

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946264B2