Sodium Methoxide → HCID 54209394, compound

HRID 1106709Notes

Reaction equation

HRID 1106709 reaction equation
Cl[C:2]1[N:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:15]=[N:16][N:17]([CH3:28])[C:18]2[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][N:19]=2)[C:4](=[O:8])[N:5]([CH3:7])[N:6]=1.[CH3:29][O-:30].[Na+]>C1COCC1.O>[CH3:29][O:30][C:2]1[N:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:15]=[N:16][N:17]([CH3:28])[C:18]2[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][N:19]=2)[C:4](=[O:8])[N:5]([CH3:7])[N:6]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 53949563HCID 53949563, compound

Product 1

HCID 54209394HCID 54209394, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound of Step B (0.38 g, 0.93 mmol) was dissolved in THF (10 mL) and then sodium methoxide (25% in methanol, 0.56 mL) was added dropwise. The mixture was heated at reflux for 1 h, cooled to room temperature and then diluted with water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous NaCl, dried (MgSO4), filtered and concentrated to an oil which was purified by flash column chromatography on silica gel to afford 0.27 g of the title compound of Step C, a compound of the invention, as a pale yellow solid melting at 185-187° C. 1H NMR (300 MHz, CDCl3): δ 8.41 (dd,1H, J=5, 1.5 Hz), 8.12 (dd,1H, J=8, 1.5 Hz), 8.01 (dd,1H, J=8, 1.5Hz), 7.42 (m,3H), 7.23 (d,1H J=8 Hz), 15 7.02 (dd,1H, J=8, 5Hz), 3.93 (s,3H), 3.56 (s,3H), 3.48 (s,3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases were washed with saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to an oil which
  8. customwas purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-6710a3e81bae412fb0bea269d2c763ff
Source dataset
uspto-grants-2000_05
Patent number
US06057352

Reaction notes

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