2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 57741572, compound

HRID 416019Notes

Reaction equation

HRID 416019 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([N:28]5[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]5)=[O:27])=[CH:22][CH:21]=4)=[CH:15][C:14]=3[Cl:34])[C:8]2=[O:35])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[F:45][C:46]([F:57])([F:56])[CH2:47]OS(C(F)(F)F)(=O)=O>C1COCC1.C(OCC)(=O)C>[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:12][C:13]3[C:14]([Cl:34])=[CH:15][C:16]([C:20]4[CH:21]=[CH:22][C:23]([C:26]([N:28]5[CH2:29][CH2:30][N:31]([CH2:47][C:46]([F:57])([F:56])[F:45])[CH2:32][CH2:33]5)=[O:27])=[CH:24][CH:25]=4)=[CH:17][C:18]=3[Cl:19])[C:8]2=[O:35])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate2×HCID 81531Diisopropylethylamine2×HCID 57741513HCID 57741513, compound

Product 1

HCID 57741572HCID 57741572, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of 1-cyclohexyl-3-[3,5-dichloro-4′-(piperazine-1-carbonyl)-biphenyl-4-ylmethyl]-pyrrolidin-2-one (0.182 g, 0.35 mmol) and N,N-diisopropyl ethyl amine (0.32 g, 2.47 mmol) in THF (10 mL) with trifluoromethane sulfonic acid 2,2,2-trifluoroethyl ester (0.41 g, 1.77 mmol) and heat to reflux for 3 hours under N2. Add more N,N-diisopropyl ethyl amine (0.13 g, 1.03 mmol) and trifluoromethane sulfonic acid 2,2,2-trifluoroethyl ester (0.24 g, 1.03 mmol) and continue to heat at reflux for 2 more hours. Cool the reaction to room temperature, dilute with ethyl acetate and wash with saturated sodium bicarbonate then water. Dry the organic layer with sodium sulfate and purify the crude product by reverse phase HPLC to afford 91 mg (43%) of the title compound: MS (m/z): 596 (M+).

Workup

  1. temperatureheat
  2. temperatureto reflux for 3 hours under N2
  3. temperatureto heat
  4. temperatureat reflux for 2 more hours
  5. temperatureCool
  6. customthe reaction to room temperature
  7. washwash with saturated sodium bicarbonate
  8. dry with materialDry the organic layer with sodium sulfate
  9. custompurify the crude product by reverse phase HPLC

Sources & evidence

ORD record
ord-617c5914622f473e96e4f59a3a38eeee
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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