Sodium Methoxide → HCID 18696618, compound

HRID 1870552Notes

Reaction equation

HRID 1870552 reaction equation
Cl[C:2]1[N:3]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([OH:19])[CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[C:4](=[O:8])[N:5]([CH3:7])[N:6]=1.[CH3:20][O-:21].[Na+]>C1COCC1>[OH:19][C:16]1[CH:17]=[C:18]2[C:13]([CH:12]=[CH:11][CH:10]=[C:9]2[N:3]2[C:2]([O:21][CH3:20])=[N:6][N:5]([CH3:7])[C:4]2=[O:8])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18696609HCID 18696609, compound

Product 1

HCID 18696618HCID 18696618, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the tide compound of Step F (3.3 g) in THF (38 mL) was added a solution of sodium methoxide (6.5 mL, 30% in methanol) while stiring under N2. The mixture was heated at 50° C. for 6 h and cooled to room temperature and left to stir overnight. The reaction was quenched with water and extracted three times with methylene chloride and then three times with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure. Trituration (ethyl acetate:hexane 1:1) of the crude product provided 1.61 g of the title compound of Step G as a light brown solid melting at greater than 250° C. 1H NMR (Me2SO-d6): δ 10.00 (s,1H), 7.93 (m,2H), 7.47 (dd,1H), 7.36 (t,1H), 7.15 (dd,1H), 6.73 (d,1H), 3.86 (s,3H), 3.39 (s,3H).

Workup

  1. temperaturecooled to room temperature
  2. waitleft
  3. customThe reaction was quenched with water
  4. extractionextracted three times with methylene chloride
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-35a8a5481825408dba3e9c0a08b1e7c6
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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