Ammonium Chloride → 4-Methoxy-2-methyl-N-(3-(trifluoromethyl)benzyl)-1,8-naphthyridine-3-carboxamide

HRID 1961469Notes

Reaction equation

HRID 1961469 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[C:3]=1[C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)=[O:14].[CH3:27][O-:28].[Na+].[NH4+].[Cl-]>CO>[CH3:27][O:28][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[C:3]=1[C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)=[O:14]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 667460894-Chloro-2-methyl-N-(3-(trifluoromethyl)benzyl)-1,8-naphthyridine-3-carboxamide

Product 1

HCID 667462884-Methoxy-2-methyl-N-(3-(trifluoromethyl)benzyl)-1,8-naphthyridine-3-carboxamideYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloro-2-methyl-N-(3-(trifluoromethyl)benzyl)-1,8-naphthyridine-3-carboxamide (60.0 mg, 0.16 mmol) was dissolved in anhydrous MeOH (1.0 ml). NaOMe was added and the mixture refluxed for 15 h. The mixture was allowed to cool. NH4Cl (5.0 ml (sat)) was added and the product extracted with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated. Purification was done by flash chromatography (EtOAc/MeOH 98:2) giving 12.0 mg (20%) of the title compound.

Workup

  1. temperaturethe mixture refluxed for 15 h
  2. temperatureto cool
  3. extractionthe product extracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-dd4863930cef4bc9a50151e0885345b6
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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