Water → HCID 66816229, compound

HRID 1697093Notes

Reaction equation

HRID 1697093 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:7]2[C:12]([C:13](=[O:26])[C:14]=1[CH2:15][C:16]1[CH:17]=[N:18][C:19]([C:22]([O:24]C)=[O:23])=[CH:20][CH:21]=1)=[CH:11][CH:10]=[C:9]([CH3:27])[N:8]=2)=[O:4].O[Li].O.O>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:7]2[C:12]([C:13](=[O:26])[C:14]=1[CH2:15][C:16]1[CH:17]=[N:18][C:19]([C:22]([OH:24])=[O:23])=[CH:20][CH:21]=1)=[CH:11][CH:10]=[C:9]([CH3:27])[N:8]=2)=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59846236HCID 59846236, compound2×

Product 1

HCID 66816229HCID 66816229, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-(6-methoxycarbonyl-pyridin-3-ylmethyl)-7-methyl-4-oxo-1-phenyl-1,4-dihydro[1,8]naphthyridine-2-carboxylic acid methyl ester (compound 100) (0.2 g) in THF (10 mL) was added LiOH.H2O (0.06 g) and H2O (2 mL), and the mixture stirred at RT for 1 h. The product was taken up in EtOAc, washed with H2O and HCl (2M, 2 mL), filtered, and worked up with EtOAc and H2O. The organic layer was dried over MgSO4, and concentrated to a yellow oil. The oil was taken up in EtOAc, washed with H2O, dried over MgSO4, and concentrated to a yellow solid to provide 3-(6-carboxy-pyridin-3-ylmethyl)-7-methyl-4-oxo-1-phenyl-1,4-dihydro[1,8]naphthyridine-2-carboxylic acid methyl ester (0.11 g). M+H=430.

Workup

  1. washwashed with H2O and HCl (2M, 2 mL)
  2. filtrationfiltered
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated to a yellow oil
  5. washwashed with H2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to a yellow solid

Sources & evidence

ORD record
ord-c6d4016baf824e8cb9344f811dc988a5
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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