N-(2-aminoethyl)-N-methylmethanesulfonamide → 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[methyl(methylsulfonyl)amino]ethyl}-1-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide
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:29])=[C:14]([C:24]([O:26]CC)=O)[C:15](=[O:23])[N:16]3[CH2:19][CH2:20][O:21][CH3:22])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:30][CH2:31][CH2:32][N:33]([CH3:38])[S:34]([CH3:37])(=[O:36])=[O:35]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:29])=[C:14]([C:24]([NH:30][CH2:31][CH2:32][N:33]([CH3:38])[S:34]([CH3:37])(=[O:36])=[O:35])=[O:26])[C:15](=[O:23])[N:16]3[CH2:19][CH2:20][O:21][CH3:22])=[N:11][CH:10]=2)=[CH:6][CH:7]=1Participants
3
Reactant 2
Product 1
Procedure
In a manner similar to that described in example 316, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (10 mg, 0.025 mmol) and N-(2-aminoethyl)-N-methylmethanesulfonamide (50 mg, 0.329 mmol) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[methyl(methylsulfonyl)amino]ethyl}-1-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (8 mg, 62% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.36 (br s, 1 H), 8.53 (s, 1 H), 7.69 (s, 1 H), 7.16-7.13 (m, 2 H), 7.02-6.98 (m, 2 H), 4.33 (m, 2 H), 4.10 (s, 2 H), 3.68-3.61 (m, 4 H), 3.39 (m, 2 H), 3.18 (s, 3 H), 2.95 (s, 3 H), 2.82 (s, 3 H); MS m/z 507 M+1).
Sources & evidence
- ORD record
- ord-12b712a478234d50ad0806956f41ff15
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691991B2
Reaction notes
Loading…