N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide → N-[2-[N-ethyl-N-[2-[(6-fluoropyridin-2-yl)amino]ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide
Reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH2:15][CH3:16])[CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[N:9]=1.C(N(CCN[C:33]([C:35]1[CH:44]=[N:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([I:45])[CH:41]=2)[N:36]=1)=[O:34])CCOC1C(F)=NC=CC=1)C>>[CH2:15]([N:4]([CH2:3][CH2:2][NH:1][C:33]([C:35]1[CH:44]=[N:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([I:45])[CH:41]=2)[N:36]=1)=[O:34])[CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[N:9]=1)[CH3:16]Participants
3
Reactant 2
Product 1
Procedure
This compound was prepared, starting from compound 15 (55 mg, 0.24 mmol), according to the procedure developed for compound 10. Reaction time under reflux: 6 h, to give compound 16 (84 mg, 0.16 mmol) as an orange-coloured oil. Yield 97%; Rf (Al2O3, CH2Cl2/EtOH, 98/2, v/v) 0.70; IR (CCl4) ν 1521, 1619, 1685, 2760-3000, 3405 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.09 (t, 3H, J=7.1 Hz), 2.72 (q, 2H, J=7.1 Hz), 2.82 (m, 2H), 3.35 (q, 2H, J=5.7 Hz), 3.63 (q, 2H, J=5.9 Hz), 5.40 (se, 1H), 6.01 (dd, 1H, J=2.3, 8.0 Hz), 6.11 (dd, 1H, J=2.3, 8.0 Hz), 7.30 (q, 1H, 4JH-F=8.0 Hz, J=8.0 Hz), 7.90 (d, 1H, J=8.8 Hz), 8.06 (dd, 1H, J=1.8, 8.8 Hz), 8.34 (se, 1H), 8.58 (d, 1H, J=1.8 Hz), 9.61 (s, 1H); ESI-MS m/z 508.9 [M+H]+.
Workup
- customThis compound was prepared
- customReaction time
- temperatureunder reflux
Sources & evidence
- ORD record
- ord-cb5af4984aea43a7bbd7861a183bfac3
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09125937B2
Reaction notes
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