N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-8-iodo-[1,6]naphthyridine-2-carboxamide → N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-8-iodo-[1,6]naphthyridine-2-carboxamide dihydrochloride salt
Reaction equation
[CH2:1]([N:3]([CH2:14][CH2:15][NH:16][C:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[C:22]([I:29])[CH:23]=[N:24][CH:25]=2)[N: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:30].Cl.C(N(CCNC(C1C=NC2C(=CC=C(I)C=2)N=1)=O)CCOC1C(F)=NC=CC=1)C>>[ClH:30].[ClH:30].[CH2:1]([N:3]([CH2:14][CH2:15][NH:16][C:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[C:22]([I:29])[CH:23]=[N:24][CH:25]=2)[N: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 73 (100 mg, 0.20 mmol), according to the procedure developed for compound 11. Reaction time at room temperature: 12 h to give compound 74 (99 mg, 0.17 mmol) as a very hygroscopic yellow solid. Yield 87%; mp 131-133° C. (dec.); IR (KBr) ν 1287, 1455, 1521, 1606, 1678, 2300-2750, 2800-3100, 3200-3500 cm−1; 1H NMR (200 MHz, DMSO-d6) δ 1.34 (t, 3H, J=7.1 Hz), 3.38 (m, 2H), 3.48 (m, 2H), 3.71 (m, 2H), 3.91 (q, 2H, J=6.1 Hz), 4.60 (t, 2H, J=4.6 Hz), 7.27 (dd, 1H, J=4.5, 8.2 Hz), 7.70 (m, 1H), 7.73 (d, 1H, J=4.5 Hz), 8.31 (d, 1H, J=8.4 Hz), 8.80 (d, 1H, J=8.4 Hz), 8.96 (t, 1H, J=6.0 Hz), 9.28 (s, 1H), 9.48 (s, 1H), 11.2 (se, 1H); ESI-MS m/z 509.9 [M+H]+.
Workup
- customThis compound was prepared
- customReaction time at room temperature
Sources & evidence
- ORD record
- ord-de29bddf79f448aeba06b543787d12b3
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09125937B2
Reaction notes
Loading…