Heptane → N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide

To a stirred solution of compound 5 (55 mg, 0.24 mmol) in anhydrous dichloromethane (3 mL) was added at 0° C., under argon, a 2.0 M trimethylaluminium solution in heptane (0.12 mL, 0.24 mmol). After 10 min, a solution of compound 9 (57 mg, 0.17 mmol) in anhydrous dichloromethane (2 mL) was added and the mixture was refluxed for 6.5 h. After cooling to room temperature, water (15 mL) was added. The mixture was decanted and the aqueous layer was extrated with dichloromethane (3×20 mL). The organic layers were combined, dried on magnesium sulfate, filtered and evaporated under reduced pressure. The residue obtained was chromatographed (Al2O3, CH2Cl2/EtOH, 98/2, v/v) to give compound 10 (84 mg, 0.16 mmol) as a brown oil. Yield 94%; Rf (Al2O3, CH2Cl2/EtOH, 98/2, v/v) 0.58; IR (CCl4) ν 1453, 1468, 1522, 1684, 2750-3000 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.12 (t, 3H, J=6.8 Hz), 2.76 (q, 2H, J=6.8 Hz), 2.89 (t, 2H, J=5.7 Hz), 3.03 (t, 2H, J=5.3 Hz), 3.64 (q, 2H, J=5.7 Hz), 4.15 (t, 2H, J=5.3 Hz), 6.99 (dd, 1H, J=4.8, 7.3 Hz), 7.23 (m, 1H), 7.59 (d, 1H, J=8.8 Hz), 7.64 (m, 1H), 8.00 (d, 1H, J=8.8 Hz), 8.43 (se, 1H), 8.57 (s, 1H), 9.61 (s, 1H); ESI-MS m/z 509.9 [M+H]+.

1. temperaturethe mixture was refluxed for 6.5 h
2. customThe mixture was decanted
3. customdried on magnesium sulfate
4. filtrationfiltered
5. customevaporated under reduced pressure
6. customThe residue obtained
7. customwas chromatographed (Al2O3, CH2Cl2/EtOH, 98/2

ORD record

ord-28503ef2244443a39561eca976157faf

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09125937B2