Potassium Carbonate → 2-[2-(3,5-Bis-trifluoromethyl-benzenesulfonylamino)-6,7-dihydro-4H-thiazolo-[5,4-c]pyridin-5-yl]-4-trifluoromethyl-benzamide

HRID 1591935Notes

Reaction equation

HRID 1591935 reaction equation
Cl.[F:2][C:3]([F:28])([F:27])[C:4]1[CH:5]=[C:6]([S:14]([NH:17][C:18]2[S:19][C:20]3[CH2:21][NH2+:22][CH2:23][CH2:24][C:25]=3[N:26]=2)(=[O:16])=[O:15])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.F[C:30]1[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[CH:35][C:31]=1[C:32]([NH2:34])=[O:33].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.CO>[F:28][C:3]([F:2])([F:27])[C:4]1[CH:5]=[C:6]([S:14]([NH:17][C:18]2[S:19][C:20]3[CH2:21][N:22]([C:30]4[CH:38]=[C:37]([C:39]([F:40])([F:42])[F:41])[CH:36]=[CH:35][C:31]=4[C:32]([NH2:34])=[O:33])[CH2:23][CH2:24][C:25]=3[N:26]=2)(=[O:15])=[O:16])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6056892-Fluoro-4-(trifluoromethyl)benzamideHCID 86608857HCID 86608857, compound

Product 1

HCID 99389462-[2-(3,5-Bis-trifluoromethyl-benzenesulfonylamino)-6,7-dihydro-4H-thiazolo-[5,4-c]pyridin-5-yl]-4-trifluoromethyl-benzamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

3.3 g of 2-(3,5-bis-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-5-ium hydrochloride, 1.545 g of 2-fluoro-4-trifluoromethyl-benzamide and 3.3 g of K2CO3 are heated in DMSO at 150° for 5 hours. From the mixture obtained solvent is evaporated, the evaporation residue obtained is dissolved in EtAc/MeOH (9/1) and the mixture obtained is extracted with 50 ml of 1 M HCl and brine. Two phases are obtained and are separated and the organic layer obtained is concentrated and subjected to chromatography. 2-[2-(3,5-Bis-trifluoromethyl-benzenesulfonylamino)-6,7-dihydro-4H-thiazolo-[5,4-c]pyridin-5-yl]-4-trifluoromethyl-benzamide is obtained and is re-crystallized from EtAc.

Workup

  1. customFrom the mixture obtained solvent
  2. customis evaporated
  3. customthe evaporation residue obtained
  4. customthe mixture obtained
  5. extractionis extracted with 50 ml of 1 M HCl and brine
  6. customTwo phases are obtained
  7. customare separated
  8. customthe organic layer obtained
  9. concentrationis concentrated

Sources & evidence

ORD record
ord-5d4c0a5163f641aa86ec465296a18c0c
Source dataset
uspto-grants-2007_11
Patent number
US07291734B2

Reaction notes

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