Pyridine → HCID 58926719, compound

HRID 2378103Notes

Reaction equation

HRID 2378103 reaction equation
N1C=CC=CC=1.[CH2:7]([O:9][C:10]([C:12]1[C:21](=[O:22])[C:20]2[C:15](=[N:16][C:17]([CH3:23])=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:11])[CH3:8].Cl[C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26]>ClCCl>[CH:28]([O:27][C:25]([N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[C:17]([CH3:23])[N:16]=2)[C:21](=[O:22])[C:12]([C:10]([O:9][CH2:7][CH3:8])=[O:11])=[CH:13]1)=[O:26])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 5373687Ethyl 7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate

Product 1

HCID 58926719HCID 58926719, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add pyridine (2.43 ml, 30.0 mmol) to a suspension of 7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (2.32 g, 10.0 mmol) in dichloromethane (100 ml), and then add isopropyl chloroformate (1.0 N in toluene, 30.0 ml). Stir the reaction mixture at room temperature overnight. Wash with brine (3×100 ml). Separate the organic layer, dry over Na2SO4, filter, and concentrate. Purify using silica gel column chromatography (gradient eluent, 0-60% ethyl acetate in hexane) to provide 7-methyl-4-oxo-4H-[1,8]naphthyridine-1,3-dicarboxylic acid 3-ethyl ester 1-isopropyl ester (1.31 g, 41%). MS (ES+): 319 (M+H).

Workup

  1. washWash with brine (3×100 ml)
  2. customSeparate the organic layer
  3. dry with materialdry over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify

Sources & evidence

ORD record
ord-d10cdf4514364383b4b73ceb90172f40
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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