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

HRID 400429Notes

Reaction equation

HRID 400429 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][CH2:28][CH:29]=[CH2:30])=[O:26])[S:23][C:17]=2[CH2:16]1)=O)(C)(C)C>C(Cl)(Cl)Cl>[CH2:28]([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])[CH:29]=[CH2:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866860332-(3-allyl-ureido)-6,7-dihydro-4H-thiazolo(5,4-c)pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 866860341-Allyl-3-(4,5,6,7-tetrahydro-thiazolo(5,4-c)pyridin-2-yl)-ureaYield 96.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

10% TFA in 60 ml chloroform was added to 2.5 g 2-(3-allyl-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 50% ethyl acetate and 50% hexane to yield 1.7 g of the desired product. (M+H)+: 239

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 50% ethyl acetate and 50% hexane

Sources & evidence

ORD record
ord-8d4809b8159c4efe82895d253f3ecbd2
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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