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

HRID 1392726Notes

Reaction equation

HRID 1392726 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 5N aqueous solution (100 ml) of potassium hydroxide and diethyl 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. Diethyl ether was added to the residue, and solids deposited were collected by filtration to obtain the title compound (3.97 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiona 5N aqueous solution (100 ml) of potassium hydroxide and diethyl 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. additionDiethyl ether was added to the residue, and solids
  9. filtrationdeposited were collected by filtration

Sources & evidence

ORD record
ord-e6ffc6f76bc5476babf4c20ca4e41f26
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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