Pyridine → 2-Phenoxycarbonylaminothiazolo[4,5-c]pyridine

HRID 615800Notes

Reaction equation

HRID 615800 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.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>CN(C=O)C>[O:20]([C:18]([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])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 14252938(1,3)Thiazolo(4,5-c)pyridin-2-amine

Product 1

HCID 155935492-Phenoxycarbonylaminothiazolo[4,5-c]pyridineYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-aminothiazolo[4,5-c]pyridine (302 mg, 2 mmoles) and pyridine (0.2 ml) in 5 ml of DMF was added phenyl chloroformate (400 mg, 2.5 mmoles), and the mixture was stirred at room temperature for 1.5 days. The crystalline precipitate was collected by filtration to afford 386 mg (71%) of the title compound. Mp. >290° C.

Workup

  1. filtrationThe crystalline precipitate was collected by filtration

Sources & evidence

ORD record
ord-90e061e55a7d4e729b9abc7088327d56
Source dataset
uspto-grants-1985_02
Patent number
US04500526

Reaction notes

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