L-Alaninol → HCID 69482119, compound

HRID 2364355Notes

Reaction equation

HRID 2364355 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.[CH3:26][C@H:27]([NH2:30])[CH2:28][OH:29]>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:30][C@@H:27]([CH3:26])[CH2:28][OH:29])=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 80307L-AlaninolHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482119HCID 69482119, 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 S-(+)-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) δ tautomers are observed 11.71 (1H, br s), 10.71 (1H, br s), 10.05 (1H, br s), 8.18 (0.59H, s), 8.14 (0.41H, s), 7.36-7.23 (3H, m), 7.14-7.08 (2H, m), 4.78 (1H, t, J=5 Hz), 3.98 (2H, s), 3.97-3.95 (1H, m), 3.49-3.41 (1H, m), 3.26-3.21 (1H, m), 1.13 (1.62H, d, J=6.6 Hz), 1.08 (1.388H, d, J=6.6 Hz); HRMS calcd for C19H18FN3O4+H+: 372.1360. Found 372.1356.

Workup

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

Sources & evidence

ORD record
ord-06821fb80a8049819c9b1be23ea594ef
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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