HCID 178418582, compound → HCID 178488112, compound

HRID 730057Notes

Reaction equation

HRID 730057 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[NH:9][C:10]([S:20][CH3:21])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[O:22]([CH3:24])[Na]>CO.O>[CH2:21]([S:20][C:10]1[NH:9][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([O:22][CH3:24])[CH:7]=2)=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[N:11]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 178418582HCID 178418582, compoundHCID 178503384HCID 178503384, compound

Product 1

HCID 178488112HCID 178488112, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 25a (0.1 g; 0.25 mmol) in methanolic NaOCH3 solution (30%, 2 ml) was diluted with methanol (5 ml) and stirred under reflux for 13 h. The reaction mixture was diluted with H2O and the aqueous solution was extracted with CH2Cl2 (3×). The combined organic extract was washed with saturated NaCl solution, dried over Na2SO4 and concentrated. The oily residue was purified by column chromatography (SiO2 60, CH2Cl2/ethyl acetate 1+1).

Workup

  1. temperatureunder reflux for 13 h
  2. extractionthe aqueous solution was extracted with CH2Cl2 (3×)
  3. extractionThe combined organic extract
  4. washwas washed with saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe oily residue was purified by column chromatography (SiO2 60, CH2Cl2/ethyl acetate 1+1)

Sources & evidence

ORD record
ord-f16a3a7390674affb91cdb4ee0a637e7
Source dataset
uspto-grants-2009_09
Patent number
US07582660B2

Reaction notes

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