2-Morpholinoethylamine → 1-[2-(Dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364199Notes

Reaction equation

HRID 2364199 reaction equation
[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24](OCC)=[O:25])[C:6]1=[O:29].[NH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>>[CH3:31][N:2]([CH3:1])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:32][CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[O:25])[C:6]1=[O:29]

Participants

3

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 58882926HCID 58882926, compound

Product 1

HCID 588829201-[2-(Dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Procedure

This compound was prepared from ethyl 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 4-(2-aminoethyl)morpholine employing methods similar to those described in Example 9. The product was obtained as a white solid: 1H NMR (CDCl3) δ 10.15 (1H, br t), 8.54 (1H, s), 7.15 (2H, dd, J=9, 6 Hz), 7.05-7.01 (3H, m), 4.96 (2H, s), 4.11 (2H, s), 3.74 (4H, m), 3.56 (2H, q, J=6 Hz), 3.13 (3H, s), 2.97 (3H, s), 2.59 (2H, t, J=6 Hz), 2.52 (4H, m); HRMS calcd for C26H30FN5O5+H+: 512.2309. Found: 512.2296.

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-2bcc27f5a807451281fbe703a797b064
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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