Isopropylamine → 6-Chloro-N-isopropylimidazo[1,2-b]pyridazine-2-carboxamide

Temperature

0 °C

Ethyl 6-chloroimidazo[1,2-b]pyridazine-2-carboxylate (250 mg, 1.11 mmol) was taken up in tetrahydrofuran and cooled to 0° C. Trimethylaluminum (6.6 mL, 13.3 mmol) was added dropwise followed by the addition of isopropylamine (0.4 mL, 2.2 mmol). The cold bath was removed and the reaction was allowed to proceed overnight at room temperature. The reaction was then quenched slowly with methanol, and stirred for 10 minutes. The resulting mixture was filtered, washing the solids with ethyl acetate and water. The filtrate was collected, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organics were concentrated under and purified via flash chromatography (0-15% methanol in dichloromethane) to afford the title compound.

1. customThe cold bath was removed
2. customThe reaction was then quenched slowly with methanol
3. filtrationThe resulting mixture was filtered
4. washwashing the solids with ethyl acetate and water
5. customThe filtrate was collected
6. customthe phases were separated
7. extractionthe aqueous layer was extracted with ethyl acetate
8. concentrationThe combined organics were concentrated under and
9. custompurified via flash chromatography (0-15% methanol in dichloromethane)

ORD record

ord-0bbd9eaa4f9441578311a211e23bd8d8

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344144B2