Cyclopropylamine → HCID 58314000, compound

Diisopropylethylamine (2.4 mL, 13.62 mmol) and cyclopropylamine (943 μL, 13.62 mmol) were added to commercially available (Ark Pharm, Inc.) 6,8-dibromoimidazo[1,2-a]pyrazine (2.51 g, 9.08 mmol) dissolved in 2-propanol (9 mL). The solution was placed in an 80° C. oil bath. After 4.5 h, the volatiles were removed in vacuo. The brown residue was partitioned between dichloromethane (50 mL) and water (50 mL). The organic layer was washed further with water (50 mL) and then brine (50 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified via a filtration over a short plug of silica gel (40% EtOAc/hexanes) and the filtrate was concentrated in vacuo to afford 6-bromo-N-cyclopropylimidazo[1,2-a]pyrazin-8-amine (2.19 g, 95%) as a light brown solid. 1H NMR (CDCl3, 400 MHz) δ: 7.61 (s, 1H), 7.46 (d, 1H, J=1.2 Hz), 7.44 (d, 1H, J=1.2 Hz), 6.26 (bs, 1H), 3.02 (dddd, 1H, J=7.2, 7.2, 7.2, 3.6 Hz), 0.89-0.95 (m, 2H), 0.64-0.69 (m, 2H).

1. customwas placed in an 80° C.
2. customthe volatiles were removed in vacuo
3. customThe brown residue was partitioned between dichloromethane (50 mL) and water (50 mL)
4. washThe organic layer was washed further with water (50 mL)
5. dry with materialThe organic layer was dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. filtrationThe residue was purified via a filtration over a short plug of silica gel (40% EtOAc/hexanes)
9. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-1571992b90654d2b89747b4b194c1178

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09303033B2