N-Boc-N-methylethylenediamine → HCID 68297219, compound

HRID 1410819Notes

Reaction equation

HRID 1410819 reaction equation
CO[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:4].[C:24]([O:28][C:29](=[O:35])[N:30]([CH2:32][CH2:33][NH2:34])[CH3:31])([CH3:27])([CH3:26])[CH3:25]>CCO>[C:24]([O:28][C:29](=[O:35])[N:30]([CH2:32][CH2:33][NH:34][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:4])[CH3:31])([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 2756424N-Boc-N-methylethylenediamineHCID 682977357-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

Product 1

HCID 68297219HCID 68297219, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (100 mg, 0.32 mmol) and (2-amino-ethyl)-methyl-carbamic acid tert-butyl ester (67 mg, 0.39 mmol) in EtOH (9 mL) was refluxed for 16 h. After cooling to r.t., the mixture was concentrated in vacuo. The residue was dissolved in EtOAc and washed with 0.1 M HCl. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (0-2% MeOH/CH2Cl2) to give 141 mg of the title compound. MS: (−) m/z 451.37 (M−1).

Workup

  1. temperaturewas refluxed for 16 h
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with 0.1 M HCl
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography (0-2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2f23234e5a624682bf62996568d6d598
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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