(S)-(+)-1-Aminopropan-2-ol → HCID 69481008, compound

HRID 2364304Notes

Reaction equation

HRID 2364304 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]([OH:30])[CH2:28][NH2:29]>>[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:29][CH2:28][C@@H:27]([OH:30])[CH3:26])=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69481008HCID 69481008, compound

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-(+)-1-amino-2-propanol employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) δ 11.82 (1H, br s), 10.35 (1H, br s), 8.50 (1H, s), 7.45 (1H, s), 7.31-7.27 (2H, m), 7.15 (2H, t, J=8.7 Hz), 4.93 (1H, d, J=4.2 Hz), 4.11 (2H, s), 3.80-3.75 (1H, m), 3.42-3.39 (1H, m), 3.20-3.14 (1H, m), 1.07 (3H, d, J=6.1 Hz); HRMS calcd for C19H18FN3O4+H+: 372.1360. Found 372.1355.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-93c85c0d04a0473593f1c56ac266463b
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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