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

HRID 2364274Notes

Reaction equation

HRID 2364274 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].[CH2:32]([O:34][CH2:35][CH2:36][NH2:37])[CH3:33]>CN(C=O)C.O>[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]([NH:37][CH2:36][CH2:35][O:34][CH2:32][CH3:33])=[O:25])[C:6]1=[O:29]

Participants

5

Reactant 2

HCID 66970EthoxyethylamineHCID 58882926HCID 58882926, compound

Product 1

HCID 694810111-[2-(Dimethylamino)-2-oxoethyl]-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (44 mg, 0.103 mmol) and 2-ethoxyethylamine (15 μL, 0.135 mmol) in DMF (0.9 mL) was heated at 100° C. for 1.5 h. The reaction mixture was diluted with water and the resulting precipitate was collected by filtration. The filter cake was washed water and MeOH and dried under vacuum to afford the product as a white solid: 1H NMR (d6-DMSO) δ 10.23 (1H, br m), 8.51 (1H, s), 7.74 (1H, s), 7.31 (2H, dd, J=8.4, 5.7 Hz), 7.12 (2H, t, J˜9 Hz), 5.12 (2H, s), 4.11 (2H, s), 3.51 (4H, s), 3.46 (2H, q, J=7 Hz), 3.12 (3H, s), 2.81 (3H, s), 1.10 (3H, t, J=7 Hz); HRMS calcd for C24H27FN4O5+H+: 471.2044. Found: 471.2050.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washThe filter cake was washed water and MeOH
  3. customdried under vacuum

Sources & evidence

ORD record
ord-fd5fcb0d06b8405fa1c829d8bcbefc6a
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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