N,N-Dimethylethylenediamine → Ethyl 6-bromo-1-[2-(dimethylamino)ethyl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1047149Notes

Reaction equation

HRID 1047149 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([CH2:12][CH2:13]OS(C)(=O)=O)[CH:7]=[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:5]2=[O:24].[CH3:25][N:26](C)[CH2:27]CN>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([CH2:12][CH2:13][N:26]([CH3:27])[CH3:25])[CH:7]=[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:5]2=[O:24]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 86665044Ethyl 6-bromo-1-{2-[(methylsulfonyl)oxy]ethyl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate2×

Product 1

HCID 68747522Ethyl 6-bromo-1-[2-(dimethylamino)ethyl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 6-bromo-1-{2-[(methylsulfonyl)oxy]ethyl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Intermediate 20, 700 mg, 1.67 mmol) in dichloromethane was purged with N,N-dimethylethane-1,2-diamine gas until the starting material disappeared. The reaction mixture was washed with water, and the organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford ethyl 6-bromo-1-[2-(dimethylamino)ethyl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 300 mg, (49%).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialthe organic layer was dried over anhydrous sodium sulphate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f30386bd19d408aafe454934dfd995b
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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