n-[2-[n-Ethyl-n-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide dihydrochloride salt → N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-7-iodophenazine-1-carboxamide dihydrochloride salt
Reaction equation
[CH2:1]([N:3]([CH2:14][CH2:15][NH:16][C:17]([C:19]1[C:32]2[C:23](=[N:24][C:25]3[C:30]([N:31]=2)=[CH:29][CH:28]=[C:27]([I:33])[CH:26]=3)[CH:22]=[CH:21][CH:20]=1)=[O:18])[CH2:4][CH2:5][O:6][C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2].[ClH:34].Cl.C(N(CCNC(C1C=NC2C(=CC=C(I)C=2)N=1)=O)CCOC1C(F)=NC=CC=1)C>>[ClH:34].[ClH:34].[CH2:1]([N:3]([CH2:14][CH2:15][NH:16][C:17]([C:19]1[C:32]2[C:23](=[N:24][C:25]3[C:30]([N:31]=2)=[CH:29][CH:28]=[C:27]([I:33])[CH:26]=3)[CH:22]=[CH:21][CH:20]=1)=[O:18])[CH2:4][CH2:5][O:6][C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
This compound was prepared, starting from compound 84 (100 mg, 0.18 mmol), according to the procedure developed for compound 11. Reaction time at room temperature: 14 h to give compound 85 (78 mg, 0.12 mmol) as a very hygroscopic orange solid. Yield 69%; mp 127-129° C. (dec.); IR (KBr) ν 1123, 1285, 1342, 1466, 1654, 2000-2750, 3100-3500 cm−1; 1H NMR (200 MHz, DMSO-d6) δ 1.35 (t, 3H, J=6.9 Hz), 3.42 (m, 2H), 3.58 (m, 2H), 3.73 (m, 2H), 4.00 (m, 2H), 4.59 (m, 2H), 7.18 (dd, 1H, J=4.9, 7.8 Hz), 7.63 (m, 2H), 8.06 (t, 1H, J=8.2 Hz), 8.23 (d, 1H, J=9.2 Hz), 8.39 (m, 2H), 8.65 (d, 1H, J=7.0 Hz), 8.73 (s, 1H), 10.51 (m, 1H), 11.14 (se, 1H); ESI-MS m/z 560.0 [M+H]+.
Workup
- customThis compound was prepared
- customReaction time at room temperature
Sources & evidence
- ORD record
- ord-1a5f723b45dc43fabd31c967fba6b802
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09125937B2
Reaction notes
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