Dimethylamine → HCID 68297703, compound

HRID 919724Notes

Reaction equation

HRID 919724 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=O.[CH3:24][NH:25][CH3:26].O>CCO>[CH3:24][N:25]([CH3:26])[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 682977357-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

Product 1

HCID 68297703HCID 68297703, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (40 mg, 0.13 mmol) and dimethylamine (0.23 mL, 1.3 mmol, 5.6 M in EtOH) in 2 mL of EtOH was heated in a sealed tube at 80° C. for 4 h. After cooling to r.t., water (3 mL) was added. The resulting suspension was filtered dried under high vacuum to afford a crude solid, which was purified by silica gel chromatography (5-40% EtOAc/hexanes+2% AcOH) to give 12 mg of the title compound. MS: (+) m/z 324.03 (M+1).

Workup

  1. temperatureAfter cooling to r.t.
  2. filtrationThe resulting suspension was filtered
  3. customdried under high vacuum
  4. customto afford a crude solid, which
  5. customwas purified by silica gel chromatography (5-40% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-f35f61e3dae946cba939cc02d014dffd
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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