2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 25110613, compound

HRID 885148Notes

Reaction equation

HRID 885148 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:31])[CH2:11][N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]4)=[C:19]([O:29][CH3:30])[CH:18]=3)[N:14]=[N:13]2)[CH:5]=[CH:6][C:7]=1[F:8].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[O:42]([CH2:50][C:51]([F:54])([F:53])[F:52])S(C(F)(F)F)(=O)=O>CN(C=O)C>[F:52][C:51]([F:54])([F:53])[C:50]([OH:29])=[O:42].[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:50][C:51]([F:54])([F:53])[F:52])[C:10](=[O:31])[CH2:11][N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]4)=[C:19]([O:29][CH3:30])[CH:18]=3)[N:14]=[N:13]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 59472622HCID 59472622, compound

Product 1

HCID 25110613HCID 25110613, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(3-chloro-4-fluorophenyl)-2-{-4-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1H-1,2,3-triazol-1-yl}acetamide (50 mg, 0.113 mmol) and KHMDS (27.1 mg, 0.136 mmol) were added to a 25-mL flask under nitrogen and DMF (3 ml) was added. Trifluoroethyl triflate (0.023 ml, 0.159 mmol) was added and the suspension stirred at room temperature for 16 h. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.1% TFA, to give the product (25 mg) as a yellow solid.

Workup

  1. customThe residue was purified by preparative HPLC Reverse phase (C-18)
  2. washeluting with Acetonitrile/Water+0.1% TFA

Sources & evidence

ORD record
ord-d87a5af84682435fad05e5523697ca92
Source dataset
uspto-grants-2012_08
Patent number
US08242150B2

Reaction notes

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