2-Aminopropanol → HCID 69482044, compound

HRID 2364226Notes

Reaction equation

HRID 2364226 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][CH:27]([NH2:30])[CH2:28][OH: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:30][CH: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

3

Reactant 2

HCID 51262-AminopropanolHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482044HCID 69482044, 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 DL-2-amino-1-propanol employing methods similar to those described in Example 2 and was obtained a white solid: 1H NMR (d6-DMSO) tautomers are observed δ 11.73 (1H, br s), 10.73 (1H, br s), 10.02 (1H, br s), 8.18 (0.56H, s), 8.14 (0.44H, s), 7.34-7.22 (3H, m), 7.14-7.09 (2H, m), 4.78 (1H, t, J=5 Hz), 3.98 (2H, s), 3.48-3.41 (1H, m), 3.23-3.20 (2H, m), 1.14 (0.58H, d, J=6.6 Hz), 1.08 (0.42H, d, J=6.6 Hz); HRMS calcd for C19H18FN3O4+H+: 372.1360. Found 372.1370.

Workup

  1. customwas obtained a white solid

Sources & evidence

ORD record
ord-be82de5d54284ec486aee6721c913194
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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