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

HRID 2104348Notes

Reaction equation

HRID 2104348 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 (kokai) No. 4-321691) (9.20 g) was dissolved in formic acid (60 mL), and the solution was heated under reflux for 4 hours. The reaction mixture was concentrated under reduced pressure, and to the residue were added 5N aqueous potassium hydroxide (100 mL) and diethyl ether to partition the residue. The organic layer was dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure. Diethyl ether was added to the residue, and the resultant precipitated solid was collected by filtration, to thereby give the title compound (3.97 g).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionto the residue were added 5N aqueous potassium hydroxide (100 mL) and diethyl ether
  5. customto partition the residue
  6. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  7. distillationthe solvent was distilled away under reduced pressure
  8. additionDiethyl ether was added to the residue
  9. customthe resultant precipitated solid
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-913cd79c1d2c42acac193258449140af
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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