Cyclobutylamine → N-Cyclobutyl-1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364277Notes

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

Participants

Reactant 2

HCID 75645Cyclobutylamine

HCID 58882926HCID 58882926, compound

Product 1

HCID 69480130N-Cyclobutyl-1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-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 cyclobutylamine employing methods similar to those described in Example 245. The product was obtained as a white solid: 1H NMR (d6-DMSO) δ 10.34 (1H, br), 8.49 (1H, br), 7.77 (1H, br), 7.30 (2H, m), 7.12 (2H, t, J=8.8 Hz), 5.10 (2H, br s), 4.39 (1H, m), 4.09 (2H, br s), 3.11 (3H, s), 2.81 (3H, s), 2.27 (2H, m), 1.99 (2H, m), 1.70 (2H, m); HRMS calcd for C24H25FN4O4+H+: 453.1938. Found: 453.1937.

Workup

customThe product was obtained as a white solid

Sources & evidence

ORD record: ord-f4dbb0a397e446a29b15fc1cc1854c8d
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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