Triethylamine → HCID 86596853, compound

Temperature

120 °C

A suspension of palladium (II) acetate (0.067 g, 0.30 mmol) and tri-o-tolylphosphine (0.271 g, 0.891 mmol) in 10 mL of MeCN was placed in a 50 mL heavy wall glass pressure flask and placed under an atmosphere of nitrogen. The mixture was stirred until homogeneous. The mixture was treated with triethylamine (1.58 mL, 11.9 mmol), 3-bromopyridine (0.430 mL, 4.46 mmol) and N-isopropyl-2-propyl-7-vinyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.92 g, 3.0 mmol). Nitrogen was bubbled through the mixture for 1 min and then the flask was sealed. The reaction was heated to 120° C. After 15 h, the homogenous orange solution was cooled to ambient temperature and concentrated under reduced pressure. The residue was partitioned between 75 mL of CHCl3 and 25 mL of 10% Na2CO3 solution. The phases were separated and the organic portion was washed with H2O (25 mL). The combined aqueous portions were back-extracted with CHCl3 (25 mL). The combined organic extracts were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield an orange solid. The solid was purified by chromatography (SiO2, 20–50% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3) to yield N1-isopropyl-2-propyl-7-(2-pyridin-3-yl-vinyl)-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.97 g) as a light yellow solid.

1. customwas placed in a 50 mL heavy wall glass pressure flask
2. customNitrogen was bubbled through the mixture for 1 min
3. customthe flask was sealed
4. temperaturethe homogenous orange solution was cooled to ambient temperature
5. concentrationconcentrated under reduced pressure
6. customThe residue was partitioned between 75 mL of CHCl3 and 25 mL of 10% Na2CO3 solution
7. customThe phases were separated
8. washthe organic portion was washed with H2O (25 mL)
9. extractionThe combined aqueous portions were back-extracted with CHCl3 (25 mL)
10. washThe combined organic extracts were washed with brine (30 mL)
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. customto yield an orange solid
15. customThe solid was purified by chromatography (SiO2, 20–50% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3)

ORD record

ord-fa1b69ebbd874a0ab4e08471ad446b83

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07163947B2