Trifluoroacetic acid → HCID 118431910, compound

HRID 2207974Notes

Reaction equation

HRID 2207974 reaction equation
[C:1]([N:8]([CH2:10][CH2:11][CH2:12][S:13]([C:16]1[CH:17]=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]3[N:32]([C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=4[F:40])[N:31]=[C:30]([C:41]([F:47])([F:46])[C:42]([F:45])([F:44])[F:43])[CH2:29]3)[CH:23]=2)[CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:14])C)(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl>[F:40][C:34]1[CH:35]=[C:36]([F:39])[CH:37]=[CH:38][C:33]=1[N:32]1[CH:28]([C:24]2[CH:23]=[C:22]([C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([S:13]([CH2:12][CH2:11][CH2:10][NH:8][CH3:1])(=[O:14])=[O:15])[CH:17]=3)[CH:27]=[CH:26][CH:25]=2)[CH2:29][C:30]([C:41]([F:46])([F:47])[C:42]([F:45])([F:43])[F:44])=[N:31]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118432009HCID 118432009, compound

Product 1

HCID 118431910HCID 118431910, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-{3′[3-(N-BOC-N-methyl-amino)-propane-1-sulfonyl]-biphenyl-3-yl}-1-(2,4-difluoro-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole (20.0 mg, 0.03 mmol) prepared in Example 85 and trifluoroacetic acid (22.3 uL, 0.29 mmol) were added at 0° C. to dichloromethane (1.0 mL). The reaction mixture was stirred at room temperature for 1 hour, quenched with a saturated solution of sodium hydrogen carbonate, and then extracted with dichloromethane three times. The combined extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a residue as a white liquid. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2) to give 5.0 mg of the titled compound as a white solid.

Workup

  1. customquenched with a saturated solution of sodium hydrogen carbonate
  2. extractionextracted with dichloromethane three times
  3. extractionThe combined extract
  4. washwas washed with brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4698a6506591486badeeb5ed31a5ffc6
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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