tert-Butyl (3-mercaptopyridin-4-yl)carbamate → Thiazolo[5,4-c]pyridine

HRID 546387Notes

Reaction equation

HRID 546387 reaction equation
C(O[C:6]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[SH:15])=O)(C)(C)C>C(O)=O>[N:8]1[C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[S:15][CH:6]=1

Participants

3

Reactant 1

HCID 22934779tert-Butyl (3-mercaptopyridin-4-yl)carbamate

Product 1

HCID 14666228Thiazolo[5,4-c]pyridineYield 45.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

4-[(tert-Butoxycarbonyl)amino]-3-mercaptopyridine (33.2 g) was dissolved in formic acid (250 ml), and the solution was heated under reflux for 3 days. The reaction mixture was concentrated under reduced pressure, and a 5N aqueous solution (100 ml) of potassium hydroxide and ether were added to the residue to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=25:1) to obtain the title compound (9.03 g) as a colorless solid.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 3 days
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiona 5N aqueous solution (100 ml) of potassium hydroxide and ether were added to the residue
  5. customto separate an organic layer
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was then distilled off under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=25:1)

Sources & evidence

ORD record
ord-f8a6645dbd3741f4a1d0f43f179b1486
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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