m-Chloroperbenzoic acid → 6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

HRID 1969653Notes

Reaction equation

HRID 1969653 reaction equation
C(C1CC(SCC(F)(F)F)CC1[C:14]1[N:18]2[C:19]3[CH:25]=[CH:24][N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:20]=3[N:21]=[CH:22][C:17]2=[N:16][N:15]=1)C.C1C=C(Cl)C=C(C(OO)=O)C=1>C(Cl)Cl>[CH3:31][Si:30]([CH3:33])([CH3:32])[CH2:29][CH2:28][O:27][CH2:26][N:23]1[C:20]2[N:21]=[CH:22][C:17]3[N:18]([CH:14]=[N:15][N:16]=3)[C:19]=2[CH:25]=[CH:24]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 585574931-(2-ethyl-4-(2,2,2-trifluoroethylthio)cyclopentyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

Product 1

HCID 673772476-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazineYield 164.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(2-ethyl-4-(2,2,2-trifluoroethylthio)cyclopentyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.100 g, 0.200 mmol, Preparation #MMM.1) in DCM (0.667 mL) was added m-CPBA (0.090 g, 0.400 mmol). The reaction stirred at ambient temperature for about 0.5 h. The reaction mixture was quenched by the addition of saturated aqueous NaHCO3 (5 mL). The aqueous portion was extracted with DCM (2×10 mL). The combined organic layers were separated, dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0-60% EtOAc in DCM to afford 1-2-ethyl-4-(2,2,2-trifluoroethylsulfonyl)cyclopentyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.095 g, 89%, 93% purity) as a clear oil: LC/MS (Table 1, Method a) Rt=2.63 min; MS m/z: 532 (M+H)+.

Workup

  1. customThe reaction mixture was quenched by the addition of saturated aqueous NaHCO3 (5 mL)
  2. extractionThe aqueous portion was extracted with DCM (2×10 mL)
  3. customThe combined organic layers were separated
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with a gradient of 0-60% EtOAc in DCM

Sources & evidence

ORD record
ord-0bad1078d6d3409694996f9f6a61fb92
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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