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

HRID 919814Notes

Reaction equation

HRID 919814 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-8a94d21a6fa34827aaea78f54b6f5d60
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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