(2R)-3-aminopropane-1,2-diol → HCID 69482110, 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:26])=[C:14]([C:21](OCC)=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:27][CH2:28][C@@H:29]([OH:32])[CH2:30][OH:31]>>[OH:32][C@@H:29]([CH2:30][OH:31])[CH2:28][NH:27][C:21]([C:14]1[C:15](=[O:20])[N:16]([CH3:19])[C:17]2[C:12]([C:13]=1[OH:26])=[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:22]Participants
3
Procedure
In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (50 mg, 0.140 mmol) and (2R)-3-amino-1,2-propanediol (0.03 mL, 0.42 mmol) was prepared N-[(2R)-2,3-dihydroxypropyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (39 mg, 68% yield) as a white solid. 1H NMR (DMSO-d 6)δ 10.44 (br s, 1 H), 8.53 (s, 1 H), 8.01 (s, 1 H), 7.40-7.36 (m, 2 H), 7.15-7.10 (m, 2 H), 5.06 (m, 1 H), 4.77 (m, 1 H), 4.16 (s, 2 H), 3.61-3.55 (m, 4 H), 3.39 (m, 1 H), 3.24 (m, 1 H); MS m/z 402 (M+1).
Sources & evidence
- ORD record
- ord-f39418655ed64ed881a3308eff4c3b65
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691991B2
Reaction notes
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