Trifluoroacetic acid → 1-Methyl-3-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-urea

HRID 239104Notes

Reaction equation

HRID 239104 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][C:18]2[N:21]=[C:22]([NH:24][C:25]([NH:27][CH3:28])=[O:26])[S:23][C:17]=2[CH2:16]1)=O)(C)(C)C>C(Cl)(Cl)Cl>[CH3:28][NH:27][C:25]([NH:24][C:22]1[S:23][C:17]2[CH2:16][NH:15][CH2:20][CH2:19][C:18]=2[N:21]=1)=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 584408222-(3-Methyl-ureido)-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 584407561-Methyl-3-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-ureaYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

10% TFA in 60 ml chloroform was added to 2.3 g 2-(3-methyl-ureido)-6,7-dihydro-4H-thiazolo-[5,4-c]pyridine-5-carboxylic acid tert-butyl ester in 28 ml chloroform and stirred for 2 h at RT. The mixture was concentrated, the residue was diluted with chloroform and basified with 2.5 M aqueous potassium carbonate solution and extracted with chloroform. The organic layer was concentrated. The residue was washed with a mixture of 50% ethyl acetate and 50% hexane to yield 1.5 g of the desired product. (M+H)+: 213

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with chloroform
  3. extractionextracted with chloroform
  4. concentrationThe organic layer was concentrated
  5. washThe residue was washed with a mixture of 50% ethyl acetate and 50% hexane

Sources & evidence

ORD record
ord-d87b4939e96d4f208a0f06cf584b4876
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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