Dipropylamine → (S)-2-(4-Chlorophenyl)-alpha-methyl-N,N-dipropyl-3H-imidazo[4,5-b]pyridine-3-acetamide

Temperature

50 °C

A solution of (S)-2-(4-chlorophenyl)-α-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0166 mole), 1,1'-carbonyldiimidazole (3.21 g, 0.0198 mole) and dry tetrahydrofuran (100 ml) was stirred at room temperature for 3 hours with nitrogen bubbling through it. A solution of dipropylamine (5.04 g, 0.050 mole) in tetrahydrofuran (7 ml) was added and the solution was heated at 50° C. overnight under nitrogen. The solvents were evaporated under reduced pressure and the resulting oil was partitioned between ethyl acetate (50 ml) and water (50 ml). The layers were separated and the aqueous layer was re-extracted with ethyl acetate (50 ml). The combined organic layers were washed once with water (50 ml) followed by two (50 ml) portions of 5% potassium hydroxide solution and then by water again (50 ml). The organic layer was dried over magnesium sulfate, charcoaled, filtered and evaporated to an oil which was crystallized from hot isopropyl ether. The solid was collected by filtration, and dried under high vacuum at room temperature to give 3.33 g (52%) of title compound, mp 96°-99° C.

1. customThe solvents were evaporated under reduced pressure
2. customthe resulting oil was partitioned between ethyl acetate (50 ml) and water (50 ml)
3. customThe layers were separated
4. extractionthe aqueous layer was re-extracted with ethyl acetate (50 ml)
5. washThe combined organic layers were washed once with water (50 ml)
6. dry with materialThe organic layer was dried over magnesium sulfate
7. filtrationfiltered
8. customevaporated to an oil which
9. customwas crystallized from hot isopropyl ether
10. filtrationThe solid was collected by filtration
11. customdried under high vacuum at room temperature

ORD record

ord-2e28e7d3e76c4188b7e99a62bad699af

Source dataset

uspto-grants-1989_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04824951