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

HRID 2364198Notes

Reaction equation

HRID 2364198 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]([O:26]CC)=O)[C:6]1=[O:29].[CH:32]1([NH2:35])[CH2:34][CH2:33]1>>[CH:32]1([NH:35][C:24]([C:7]2[C:6](=[O:29])[N:5]([CH2:4][C:3]([N:2]([CH3:1])[CH3:31])=[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:26])[CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 58882926HCID 58882926, compound

Product 1

HCID 58882916N-Cyclopropyl-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 cyclopropylamine employing methods similar to those described in Example 9. The product was obtained as a white solid: 1H NMR (CDCl3) δ 9.96 (1H, br), 8.54 (1H, d, J=1.4 Hz), 7.13 (2H, m), 7.04-7.00 (3H, m), 4.92 (2H, s), 4.10 (2H, s), 3.11 (3H, s), 2.96 (3H, s), 2.93 (1H, m), 0.86 (2H, m, J=13, 7), 0.66 (2H, m); HRMS calcd for C23H23FN4O4+H+: 439.1781. Found: 439.1774.

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-f0205cb7aba043fd90c0d134343f83da
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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