N-(2-aminoethyl)-N-methylmethanesulfonamide → 1-[2-(Dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide
Reaction equation
[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24](OCC)=[O:25])[C:6]1=[O:29].[NH2:32][CH2:33][CH2:34][N:35]([CH3:40])[S:36]([CH3:39])(=[O:38])=[O:37]>>[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:32][CH2:33][CH2:34][N:35]([CH3:40])[S:36]([CH3:39])(=[O:38])=[O:37])=[O:25])[C:6]1=[O:29]Participants
Procedure
This compound was prepared from ethyl 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and N-(2-aminoethyl)-N-methylmethanesulfonamide employing methods similar to those described in Example 245 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 cream-colored solid: 1H NMR (d6-DMSO) δ 10.20 (1H, br t, J=6 Hz), 8.51 (1H, s), 7.76 (1H, s), 7.31 (2H, dd, J=8.3, 6 Hz), 7.12 (2H, t, J=˜9 Hz), 5.12 (2H, s), 4.11 (2H, s), 3.55 (2H, q, J=6 Hz), 3.25 (2H, m), 3.12 (3H, s), 2.85 (3H, s), 2.81 (3H, s), 2.79 (3H, s); HRMS calcd for C24H28FN5O6+H+: 534.1823. Found: 534.1812.
Workup
- customwas purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase)
- customThe product was obtained as a cream-colored solid
Sources & evidence
- ORD record
- ord-7b0e15eaab844aa18db7a52dc95150f1
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691991B2
Reaction notes
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