N,N-Dimethyl-1,3-propanediamine → 2-(3-Chlorophenyl)-N-[3-(dimethylamino)propyl]-3H-imidazo [4,5-b]pyridine-3-acetamide hydrochloride

A solution of 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.76 g, 0.020 mole), 1,1'-carbonyldiimidazole (3.24 g, 0.020 mole), and anhydrous tetrahydrofuran (250 ml) was stirred at room temperature with a stream of nitrogen bubbling through it for 2 hrs. The nitrogen flow was stopped and a solution of 3-dimethylaminopropylamine (2.04 g, 0.020 mole) in dry tetrahydrofuran (50 ml) was added. The solution was stoppered and stirred at room temperature over the weekend. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate (100 ml) and 5% potassium hydroxide (50 ml). The layers were separated and the aqueous portion washed with ethyl acetate (50 ml). The combined organic portions were washed with 5% potassium hydroxide solution (25 ml), water (25 ml), brine (25 ml), dried over sodium sulfate, and concentrated in vacuo. The solid residue was converted to the dihydrochloride salt and crystallized from acetone-ethanol-tetrahydrofuran to give 3.23 g (36%) of a white granular solid, mp. 203°-209° C. with decomposition.

1. concentrationThe reaction mixture was concentrated in vacuo
2. custompartitioned between ethyl acetate (100 ml) and 5% potassium hydroxide (50 ml)
3. customThe layers were separated
4. washthe aqueous portion washed with ethyl acetate (50 ml)
5. washThe combined organic portions were washed with 5% potassium hydroxide solution (25 ml), water (25 ml), brine (25 ml)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customcrystallized from acetone-ethanol-tetrahydrofuran

ORD record

ord-fd7d81d1e6af41efaf60b222cbde5bd2

Source dataset

uspto-grants-1989_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04824951