Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate → HCID 69482492, compound

HRID 2364356Notes

Reaction equation

HRID 2364356 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:25])=[C:14]([C:20](OCC)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1>CN(C)C=O>[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:25])=[C:14]([C:20]([NH:11][C@H:12]([CH3:17])[CH2:13][OH:25])=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482492HCID 69482492, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and R-(−)-2-amino-1-propanol employing methods similar to those described in Example 2 and using N,N-dimethylformamide as the reaction solvent. The product was obtained as an off-white solid: 1H NMR (d6-DMSO) tautomers are observed δ 11.72 (1H, br s), 10.70 (1H, br s), 10.04 (1H, br s), 8.17 (0.23H, s), 8.14 (0.77H, s), 7.34-7.22 (3H, m), 7.14-7.08 (2H, m), 4.79-4.77 (1H, m), 3.98 (2H, s), 3.97-3.92 (1H, m), 3.29-3.21 (1H, m), 1.13 (1.65H, d, J=6.6 Hz),1.08 (1.35H, d, J=6.6 Hz); HRMS calcd for C19H18FN3O4+H+: 372.1354. Found 372.1361.

Workup

  1. customThe product was obtained as an off-white solid

Sources & evidence

ORD record
ord-c53537ae3c1444bd8dd1ec3abdbd2399
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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