Pyridine → N-(thiazolo[4,5-c]pyridin-2-yl)acetamide

HRID 615793Notes

Reaction equation

HRID 615793 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.N1C=CC=CC=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>C(Cl)Cl>[C:17]([NH:1][C:2]1[S:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14252938(1,3)Thiazolo(4,5-c)pyridin-2-amine

Product 1

HCID 15593545N-(thiazolo[4,5-c]pyridin-2-yl)acetamideYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-aminothiazolo[4,5-c]pyridine [prepared according to the procedure in T. Takahashi et al., Pharm. Bull. (Japan) 2, 34 (1954)] (151 mg, 1 mmole) in acetic anhydride (1 ml) was added pyridine (1 ml), and the mixture was heated at 100°-120° C. for an hour. After cooling, the mixture was diluted with CH2Cl2 (20 ml). The resulting precipitate was collected by filtration and recrystallized from methanol (20 ml) to give 90 mg of the title compound as fine needles (46%). Mp. >212° C. (sub.).

Workup

  1. customprepared
  2. temperaturethe mixture was heated at 100°-120° C. for an hour
  3. temperatureAfter cooling
  4. filtrationThe resulting precipitate was collected by filtration
  5. customrecrystallized from methanol (20 ml)

Sources & evidence

ORD record
ord-6bf54af24dff478f8ba524d9b280aff5
Source dataset
uspto-grants-1985_02
Patent number
US04500526

Reaction notes

Loading…