(2R)-1-aminopropan-2-ol → HCID 69482622, compound

HRID 2364292Notes

Reaction equation

HRID 2364292 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 439938(2R)-1-aminopropan-2-olHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482622HCID 69482622, 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 R-(−)-1-amino-2-propanol employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) tautomers are observed δ 11.81 (1H, t, J=5.7), 10.81 (1H, br s), 10.10 (1H, br s), 8.18 (0.58H, s), 8.15 (0.42H, s), 7.36-7.23 (3H, m), 7.15-7.08 (2H, m), 4,74 (1H, t, J=4.4 Hz), 3.98 (2H, s), 3.75-3.65 (1H, m), 3.26-3.15 (2H, m), 1.06 (3H, m); HRMS calcd for C19H18FN3O4+H+: 372.1360. Found 372.1367.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-7b6f5e06a0fe416c95564bf20fb342bb
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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