Dimethyl Sulfoxide → HCID 11465614, compound

HRID 724482Notes

Reaction equation

HRID 724482 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[C:11]2[N:12]=[CH:13][N:14]=[C:15]([OH:16])[C:10]2=[N:9]1.C([O-])([O-])=O.[Cs+].[Cs+].CS(C)=O.FC(F)(F)S(O[CH2:44][C:45]([F:48])([F:47])[F:46])(=O)=O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:20][CH:19]=2)=[C:11]2[N:12]=[CH:13][N:14]([CH2:44][C:45]([F:48])([F:47])[F:46])[C:15](=[O:16])[C:10]2=[N:9]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 178517944HCID 178517944, compound

Product 1

HCID 11465614HCID 11465614, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 2-(2-chlorophenyl)-3-(4-(trifluoromethyl)phenyl)-2H-pyrazolo[4,3-d]pyrimidin-7-ol (I-2A-2b: 100 mg, 0.26 mmol) and Cs2CO3(85 mg, 0.26 mmol) in DMF (1.5 ml) was added a DMSO solution (0.1 ml) of 2,2,2-trifluoroethyl trifluoromethanesulfonate (60 mg, 0.26 mmol). After stirring overnight, the reaction mixture was extracted from water with ethyl acetate. The organic solution was washed with half saturated aqueous NaCl and then concentrated in vacuo. The crude residue was purified on a Biotage™ Flash 12S column using 20% ethyl acetate in hexanes as eluant to give the title compound 2A-2 (65 mg, 53%) as a solid: +ES MS (M+1) 473.4; 1H NMR (CD3OD) δ 8.17 (s, 1H), 7.73–7.52 (m, 8H), 4.83 (q, J=9.1 Hz, 2H).

Workup

  1. extractionthe reaction mixture was extracted from water with ethyl acetate
  2. washThe organic solution was washed with half saturated aqueous NaCl
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified on a Biotage™ Flash 12S column

Sources & evidence

ORD record
ord-4dd4c240106644c781683fa9eb49d028
Source dataset
uspto-grants-2006_11
Patent number
US07141669B2

Reaction notes

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