Dichloromethane → HCID 118432003, compound

HRID 2207971Notes

Reaction equation

HRID 2207971 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[N:16]1[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[CH2:28][CH2:29][NH:30][CH2:31][CH:32]=3)[CH:22]=2)[CH2:19][C:18]([C:33]([F:39])([F:38])[C:34]([F:37])([F:36])[F:35])=[N:17]1.C(N(CC)CC)C.[CH3:47][S:48](Cl)(=[O:50])=[O:49].ClCCl>O>[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[N:16]1[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[CH2:28][CH2:29][N:30]([S:48]([CH3:47])(=[O:50])=[O:49])[CH2:31][CH:32]=3)[CH:22]=2)[CH2:19][C:18]([C:33]([F:38])([F:39])[C:34]([F:36])([F:37])[F:35])=[N:17]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 118432027HCID 118432027, compound

Product 1

HCID 118432003HCID 118432003, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(2,4-difluoro-phenyl)-5-[3-(1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole trifluoroacetate (30.0 mg, 0.05 mmol) prepared in Example 61, triethylamine (20.3 uL, 0.15 mmol) and methanesulfonyl chloride (1.9 uL, 0.06 mmol) were added at 0° C. to dichloromethane (1.0 mL). The reaction mixture was stirred at room temperature for 2 hours. Distilled water was added to the reaction mixture, which was then extracted with dichloromethane two times. The combined extract was washed with a 1N hydrochloric acid solution, a saturated sodium carbonate solution, and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3) to give 1.9 mg of the titled compound as a yellow liquid.

Workup

  1. extractionwas then extracted with dichloromethane two times
  2. extractionThe combined extract
  3. washwas washed with a 1N hydrochloric acid solution
  4. dry with materiala saturated sodium carbonate solution, and brine, dried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow liquid residue
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3)

Sources & evidence

ORD record
ord-25b7ad61d39146fe893540e49f420426
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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