Acetic Acid → HCID 68297612, compound

HRID 919805Notes

Reaction equation

HRID 919805 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:34])[NH:30][CH2:31][CH2:32][NH2:33])([CH3:27])([CH3:26])[CH3:25].CC(O)=O>CCO>[C:24]([O:28][C:29](=[O:34])[NH:30][CH2:31][CH2:32][NH:33][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])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 187201N-BOC-ethylenediamineHCID 682977357-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

Product 1

HCID 68297612HCID 68297612, compoundYield 80.5%

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)-carbamic acid tert-butyl ester (62 mg, 0.39 mmol) in EtOH (9 mL) was refluxed for 16 h. After cooling to r.t., AcOH (0.2 mL) was added, and the mixture was concentrated in vacuo. The residue was partitioned between water and EtOAc. The aqueous layer was extracted with additional EtOAc, and the organic layers were combined and washed with 0.1 M HCl and brine. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to give 113 mg of the title compound as an off-white solid. MS: (−) m/z 437.33 (M−1).

Workup

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

Sources & evidence

ORD record
ord-b07f311ae5b3488f888ebbef9e7d8d23
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

Loading…