Sodium Methoxide → HCID 66746054, compound

HRID 1961482Notes

Reaction equation

HRID 1961482 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([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])[C:6]([CH3:12])=[N:7]2.[CH3:27][O-:28].[Na+]>CO>[CH3:27][O:28][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([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])[C:6]([CH3:12])=[N:7]2

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 66745521HCID 66745521, compound

Product 1

HCID 66746054HCID 66746054, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Chloro-2-methyl-N-(3-(trifluoromethyl)benzyl)-1,8-naphthyridine-3-carboxamide (100 mg, 0.26 mmol) was dissolved in MeOH (10 ml) together with sodium methoxide (30 mg, 0.55 mmol) and refluxed for 18 hours. The reaction was cooled and evaporated, the residue was purified by flash chromatography using CH2Cl2/CH3OH (20:1→10:1) as eluent to give 77 mg (79%) of 5-methoxy-2-methyl-N-(3-(trifluoromethyl)benzyl)-1,8-naphthyridine-3-carboxamide as a pale mass.

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureThe reaction was cooled
  3. customevaporated
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-f0e865aa3c084ae6aa9492416137dd87
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

Loading…