Potassium Carbonate → HCID 178489146, compound

HRID 1774712Notes

Reaction equation

HRID 1774712 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][C:16]=3[C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[N:11](S(C3C=CC(C)=CC=3)(=O)=O)[N:10]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O.C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][C:16]=3[C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[NH:11][N:10]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 2

HCID 11430Potassium CarbonateHCID 90226369HCID 90226369, compound

Product 1

HCID 178489146HCID 178489146, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of compound 39 (35 mg, 00758 mmol) in methanol (10 mL) and water (5 mL) was added potassium carbonate (20 mg, 0.151 mmol) and the RM heated to 60° C. overnight. After completion of the SM, the RM was completely distilled off, diluted with water and extracted with chloroform twice. The organic layer was dried over sodium sulphate and the solvent was completely distilled off to get the crude product, which was passed through 100-200 mesh silica gel eluting the compound at 28-30% ethyl acetate in hexane as eluent to get the pale yellow colored solid of compound 40. 1H NMR (CDCl3) δ: 10.71 (s, 1H), 8.57 (d, 1H), 7.18 (m, 4H), 7.09 (m, 1H), 6.92 (m,1H), 6.74 (m,1H), 3.81 (s, 3H) and MS m/z=307.9.

Workup

  1. distillationAfter completion of the SM, the RM was completely distilled off
  2. additiondiluted with water
  3. extractionextracted with chloroform twice
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. distillationthe solvent was completely distilled off
  6. customto get the crude product, which

Sources & evidence

ORD record
ord-b5190e2f61c945d6810e0c3bbee6a90a
Source dataset
uspto-grants-2016_02
Patent number
US09260426B2

Reaction notes

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