Methanol → Ethyl 8-morpholinoimidazo[1,2-b]pyridazine-2-carboxylate

Compound 5b (8.6 g, 28 mmol) was suspended in THF (100 mL)/MeOH (50 mL). The reaction mixture was purged with argon, and 10% Pd/C (1.5 g, 1.4 mmol) was added followed by solid ammonium formate (8.7 g, 140 mmol). The reaction mixture was stirred under reflux for 1 h, during which time some of the ammonium formate sublimed onto the reflux condenser. The solid was rinsed back into the reaction flask with dry MeOH. The reaction mixture was filtered through a pad of diatomaceous earth. The filtrate was concentrated in vacuo to obtain a solid, which was dissolved in DCM (200 mL), and washed with water (100 mL) and brine (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated to give compound 5c as a white solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.34 (s, 1H), 8.04 (d, J=5.6 Hz, 1H), 6.06 (d, J=5.6 Hz, 1H), 4.43 (q, J=7.1 Hz, 2H), 3.98-4.07 (m, 4H), 3.88-3.96 (m, 4H), 1.42 (t, J=7.1 Hz, 3H).

1. additionwas added
2. washThe solid was rinsed back into the reaction flask with dry MeOH
3. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
4. concentrationThe filtrate was concentrated in vacuo
5. customto obtain a solid, which
6. washwashed with water (100 mL) and brine (100 mL)
7. dry with materialThe organic layer was dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-af07206072d8419b86d18afd7f478ff7

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193736B2