Sodium Hydroxide → HCID 69482132, 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:33])=[C:14]([C:27]([NH:29][CH2:30][CH2:31][OH:32])=[O:28])[C:15](=[O:26])[N:16]3[CH2:19][C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[Na+:35]>>[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]([O-:33])=[C:14]([C:27]([NH:29][CH2:30][CH2:31][OH:32])=[O:28])[C:15](=[O:26])[N:16]3[CH2:19][C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[Na+:35]Participants
3
Procedure
In a manner similar to that described in example 474, from 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-[(1-methyl-1H-imidazol-2-yl)methyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (336 mg, 0.744 mmol described in example 468) and 1 N sodium hydroxide was prepared sodium 7-[(4-fluorophenyl)methyl]-3-{[(2-hydroxyethyl)amino]carbonyl}-1-[(1-methyl-1H-imidazol-2-yl)methyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-4-olate (324 mg, 92% yield) as a white solid. 1H NMR (DMSO-d6) δ 10.61 (s, 1 H), 8.16 (s, 1 H), 7.95 (s, 1 H), 7.27 (m, 2 H), 7.08 (m, 2 H), 6.98 (s, 1 H), 6.73 (s, 1 H), 5.36 (s, 2 H), 4.76 (br s, 1 H), 3.95 (s, 2 H), 3.62 (s, 3 H), 3.46 (br s, 2 H), 3.30 (br s, 2 H); MS m/z 452 (M+1).
Sources & evidence
- ORD record
- ord-f1ecb18d273c4edaa1f910b840e6b12f
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691991B2
Reaction notes
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