Trifluoroacetic acid → HCID 178486158, compound

HRID 230194Notes

Reaction equation

HRID 230194 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[F:32])=[N:14][C:15]=2[CH2:17][S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[N:10](COCC[Si](C)(C)C)[N:9]=1.FC(F)(F)C(O)=O.[BH4-].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[F:32])=[N:14][C:15]=2[CH2:17][S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[NH:10][N:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 68877139HCID 68877139, compound

Product 1

HCID 178486158HCID 178486158, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

C-[3-(2-Chloro-phenyl)-6-(2,4-difluoro-phenoxy)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-N,N-dimethyl-methanesulfonamide (273 mg, 0.447 mmol) was dissolved in 5 mL chloroform, and 2.5 mL of trifluoroacetic acid was added. The reaction mixture was stirred for 22 hours at room temperature, and was then concentrated to dryness under reduced pressure. The residue was dissolved in 7 mL of MeOH, and sodium borohydride (109 mg, 4.47 mmol) was added. The reaction mixture was stirred for 15 minutes, then concentrated under reduced pressure. The residue was partitioned between 100 mL EtOAc and 100 mL brine, and the organic layer was separated, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (0% to 40% EtOAc in hexanes) to yield 167 mg of C-[3-(2-Chloro-phenyl)-6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-N,N-dimethyl-methanesulfonamide. Mass Spec. M+H=481.

Workup

  1. concentrationwas then concentrated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in 7 mL of MeOH
  3. stirringThe reaction mixture was stirred for 15 minutes
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between 100 mL EtOAc and 100 mL brine
  6. customthe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified via flash chromatography (0% to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-68609b2e09c048c389da1047a582d62b
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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