Ethoxyethylamine → HCID 69482673, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:34])=[C:14]([C:29](OCC)=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][C:20](=[O:27])[N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:35]([O:37][CH2:38][CH2:39][NH2:40])[CH3:36]>>[CH2:35]([O:37][CH2:38][CH2:39][NH:40][C:29]([C:14]1[C:15](=[O:28])[N:16]([CH2:19][C:20](=[O:27])[N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[C:17]2[C:12]([C:13]=1[OH:34])=[N:11][CH:10]=[C:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH:18]=2)=[O:30])[CH3:36]Participants
3
Procedure
This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-oxo-2-(1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-ethoxyethylamine employing methods similar to those those described in Example 9 and was purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase). The product was obtained as a white solid: 1H NMR (CDCl3) δ 14.4 (1H, br), 10.18 (1H, m), 8.55 (1H, s), 7.15 (2H, dd, J=8.4, 5.5 Hz), 7.02 (2H, t, J=8.4 Hz), 6.98 (1H, s), 4.94 (2H, s), 4.11 (2H, s), 3.61 (4H, m), 3.59-3.43 (6H, m), 1.68 (2H, m), 1.54 (4H, m), 1.21 (3H, t, J=7 Hz); HRMS calcd for C27H31FN4O5+H+: 511.2357. Found: 511.2366.
Workup
- customwas purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase)