Methanol → HCID 23144695, compound

HRID 1967805Notes

Reaction equation

HRID 1967805 reaction equation
[C:1]([C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([CH2:20]Cl)[CH:15]=2)=[O:13])=[N:8][C:7]=1[C:22]1[O:23][CH:24]=[CH:25][CH:26]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[H-].[Na+].[OH2:29].[CH3:30]O>>[C:1]([C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][O:29][CH3:30])[CH:15]=2)=[O:13])=[N:8][C:7]=1[C:22]1[O:23][CH:24]=[CH:25][CH:26]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24758Sodium hydrideHCID 23144626N-[5-Butyryl-4-(2-furyl)thiazol-2-yl]-2-(chloromethyl)pyridine-4-carboxamide

Product 1

HCID 23144695HCID 23144695, compoundYield 55%

Procedure

Compound 387 (262 mg, 0.671 mmol) was dissolved in methanol (5 mL), and 55% sodium hydride (34.0 mg, 0.775 mmol) was added thereto, followed by stirring under heating and reflux for 4 hours. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=99:1) to afford the entitled Compound 388 (142 mg, 55%).

Workup

  1. temperatureunder heating
  2. temperaturereflux for 4 hours
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=99:1)

Sources & evidence

ORD record
ord-f8c88866e4384a978bdee5ba8a7a7bb1
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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