Methanol → HCID 59846234, compound

HRID 1697090Notes

Reaction equation

HRID 1697090 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]([N:6]([C:13]1[C:18]([C:19](=[O:29])[CH2:20][CH2:21][C:22]2[CH:23]=[N:24][C:25]([Cl:28])=[CH:26][CH:27]=2)=[CH:17][CH:16]=[C:15]([CH3:30])[N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.CO.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:1][O:2][C:3]([C:4]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]2[C:18]([C:19](=[O:29])[C:20]=1[CH2:21][C:22]1[CH:23]=[N:24][C:25]([Cl:28])=[CH:26][CH:27]=1)=[CH:17][CH:16]=[C:15]([CH3:30])[N:14]=2)=[O:31]

Participants

6

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86624856HCID 86624856, compound

Product 1

HCID 59846234HCID 59846234, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{-3-[3-(6-chloropyridin-3-yl)-propionyl]-6-methyl-pyridin-2-yl}-N-phenyl-oxalamic acid methyl ester in toluene was added MeOH, and the mixture placed in a pre-heated hot bath at 80° C. K2CO3 (0.9 g) was added, which produced an immediate color change. The mixture was cooled to RT, diluted with EtOAc, and washed with LiCl (0.3 wt % aq, 2×). The organic layer was dried over MgSO4, filtered, and concentrated. The product was dissolved in hot EtOAc, and allowed to cool to RT. The resulting precipitate was filtered and washed with EtOAc to provide 3-(6-chloro-pyridin-3-ylmethyl)-7-methyl-4-oxo-1-phenyl-1,4-dihydro[1,8]naphthyridine-2-carboxylic acid methyl ester (compound 83) (0.14 g) as a tan solid. M+H=420, mp=220.0-220.5.

Workup

  1. customthe mixture placed in a pre-heated hot bath at 80° C
  2. customwhich produced an immediate color change
  3. washwashed with LiCl (0.3 wt % aq, 2×)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe product was dissolved in hot EtOAc
  8. temperatureto cool to RT
  9. filtrationThe resulting precipitate was filtered
  10. washwashed with EtOAc

Sources & evidence

ORD record
ord-2e5833c3ac9c413cbbab0059ce4ff3f9
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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