Water → 1-(2-chloro-phenyl)-5-[4-(1-methanesulfonyl-1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole

HRID 2207959Notes

Reaction equation

HRID 2207959 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH:19]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=3)=[CH:22][CH:21]=2)[CH2:18][C:17]([C:32]([F:38])([F:37])[C:33]([F:36])([F:35])[F:34])=[N:16]1.C(N(CC)CC)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48].O>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH:19]([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH2:27][CH2:28][N:29]([S:47]([CH3:46])(=[O:49])=[O:48])[CH2:30][CH:31]=3)=[CH:24][CH:25]=2)[CH2:18][C:17]([C:32]([F:38])([F:37])[C:33]([F:34])([F:35])[F:36])=[N:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1184317931-(2-chloro-phenyl)-5-[4-(1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole trifluoroacetate

Product 1

HCID 1184317951-(2-chloro-phenyl)-5-[4-(1-methanesulfonyl-1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-pentafluoroethyl-4,5-dihydro-1H-pyrazoleYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-chloro-phenyl)-5-[4-(1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole trifluoroacetate (80.0 mg, 0.14 mmol) prepared in Example 10 in dichloromethane (1.0 mL), was added triethylamine (59.0 uL, 0.43 mmol). Methanesulfonyl chloride (16.5 uL, 0.22 mmol) was dropwisely added at 0° C. to the reaction mixture, which was then stirred at room temperature for 2 hours. Distilled water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with 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=1/2) to give 50.8 mg of the titled compound as a pale yellow liquid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a yellow liquid residue
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2)

Sources & evidence

ORD record
ord-0c9f0a9699124c98a7d76dd22784f388
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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