HCID 178418597, compound → Thiazolo[4,5-c]pyridine

HRID 546427Notes

Reaction equation

HRID 546427 reaction equation
C(O[C:6]([NH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[SH:15])=O)(C)(C)C>C(O)=O>[S:15]1[C:14]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:8]=[CH:6]1

Participants

3

Reactant 1

HCID 178418597HCID 178418597, compound

Product 1

HCID 585837Thiazolo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

3-(tert-Butoxycarbonylamino)-4-mercaptopyridine (Japanese Patent Application Laid-Open No. 321691/1992) (9.20 g) was dissolved in formic acid (60 ml) and heated under reflux for 4 hours. The reaction mixture was concentrated under reduced pressure, and a 4N aqueous solution (100 ml) of potassium hydroxide and ether were added to the residue to conduct liquid separation. The resultant organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Ether was added to the residue, and solids deposited were collected by filtration to obtain the title compound (3.97 g) as a colorless solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiona 4N aqueous solution (100 ml) of potassium hydroxide and ether were added to the residue
  5. customliquid separation
  6. dry with materialThe resultant organic layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionEther was added to the residue, and solids
  9. filtrationdeposited were collected by filtration

Sources & evidence

ORD record
ord-a9cd4783601f42dfbcfa954fd862d811
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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