Glycine ethyl ester → N-[[2(3-Chlorophenyl)-3H-imidazo[4,5-b]pyridin-3-yl]acetyl]glycine ethyl ester

A solution of 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (9.50 g, 0.033 mole), 1,1'-carbonyldiimidazole (5.35 g, 0.033 mole) and anhydrous tetrahydrofuran (300 ml) was stirred at room temperature for 2 hrs with a stream of nitrogen bubbling through it. To the resulting suspension was added glycine ethyl ester (8.0 g, 0.078 mole) and the solution stirred over the weekend. The reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was partitioned between ethyl acetate (150 ml) and potassium bicarbonate solution (75 ml). The organic layer was washed with potassium bicarbonate solution (2×50 ml), water (50 ml), brine (25 ml), dried over sodium sulfate, and concentrated in vacuo. The residue (10 g) was recrystallized from tetrahydrofuran-isopropyl ether to give 6.93 g (56%) of an off-white solid, m.p. 144°-145° C.

1. filtrationThe reaction mixture was filtered
2. concentrationthe filtrate concentrated in vacuo
3. customThe residue was partitioned between ethyl acetate (150 ml) and potassium bicarbonate solution (75 ml)
4. washThe organic layer was washed with potassium bicarbonate solution (2×50 ml), water (50 ml), brine (25 ml)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. customThe residue (10 g) was recrystallized from tetrahydrofuran-isopropyl ether

ORD record

ord-cfb85c02f64f44b19e92f501af301457

Source dataset

uspto-grants-1990_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04948800