N-(2-aminoethyl)-N-methylmethanesulfonamide → 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-{2-[methyl(methylsulfonyl)amino]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](OCC)=[O:25])[C:15](=[O:23])[N:16]3[CH2:19][CH2:20][CH2:21][OH: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:25])[C:15](=[O:23])[N:16]3[CH2:19][CH2:20][CH2:21][OH:22])=[N:11][CH:10]=2)=[CH:6][CH:7]=1Participants
Procedure
In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (60 mg, 0.15 mmol) and N-(2-aminoethyl)-N-methylmethanesulfonamide (100 mg, 0.657 mmol) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (18 mg, 24% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.31 (br s, 1 H), 8.58 (s, 1 H), 7.49 (s, 1 H), 7.18-7.14 (m, 2 H), 7.05-6.99 (m, 2 H), 4.37 (m, 2 H), 4.14 (s, 2 H), 3.67 (m, 2 H), 3.51 (m, 2 H), 3.41 (m, 2 H), 2.95 (s, 3 H), 2.83 (s, 3 H), 1.83 (m, 2 H); HRMS m/z calcd for C23H28N4O6FS: 507.1714. Found: 507.1712.
Sources & evidence
- ORD record
- ord-52e378bb89064a6fa28881b759a7b868
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691991B2
Reaction notes
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