Methanol → HCID 25118716, compound

HRID 1697110Notes

Reaction equation

HRID 1697110 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]([N:6]([C:13]1[C:18]([C:19](=[O:25])[CH2:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)=[CH:17][CH:16]=[C:15]([CH3:26])[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:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:13]2[C:18]([C:19](=[O:25])[C:20]=1[CH2:21][CH:22]1[CH2:23][CH2:24]1)=[CH:17][CH:16]=[C:15]([CH3:26])[N:14]=2)=[O:27]

Participants

6

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 66817162HCID 66817162, compound

Product 1

HCID 25118716HCID 25118716, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To N-[3-(3-cyclopropyl-propionyl)-6-methyl-pyridin-2-yl]-N-phenyl-oxalamic acid methyl ester (˜0.3 g) dissolved in toluene was added MeOH (5 mL) and K2CO3 (0.3 g). The mixture was heated to 80° C. for 30 min, cooled to RT, then taken up in EtOAc and washed 2× with LiCl (0.3 wt %, aq). The product was dried over MgSO4, filtered and concentrated, then purified by prep TLC (1:4 EtOAc/hexane) to provide 3-cyclopropylmethyl-7-methyl-4-oxo-1-phenyl-1,4-dihydro[1,8]naphthyridine-2-carboxylic acid methyl ester (compound 142).

Workup

  1. temperaturecooled to RT
  2. washwashed 2× with LiCl (0.3 wt %, aq)
  3. dry with materialThe product was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by prep TLC (1:4 EtOAc/hexane)

Sources & evidence

ORD record
ord-74e34fff67f14537aa36e8d8a217a01f
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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