Dichloromethane → HCID 118432089, compound

HRID 2208007Notes

Reaction equation

HRID 2208007 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[N:25]=[C:24]([C:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=3)[CH:23]=[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].ClCCl>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[N:25]=[C:24]([C:26]3[CH2:27][CH2:28][N:29]([S:47]([CH3:46])(=[O:49])=[O:48])[CH2:30][CH:31]=3)[CH:23]=[CH:22][CH:21]=2)[CH2:18][C:17]([C:32]([F:38])([F:37])[C:33]([F:34])([F:36])[F:35])=[N:16]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 118431831HCID 118431831, compound

Product 1

HCID 118432089HCID 118432089, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(2-Chloro-phenyl)-5-[2-(1,2,3,6-tetrahydropyridin-4-yl)-pyridin-6-yl]-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole trifluoroacetate (20.0 mg, 0.04 mmol) prepared in Step 1, triethylamine (15.0 uL, 0.11 mmol) and methanesulfonyl chloride (4.1 uL, 0.05 mmol) were added at 0° C. to dichloromethane (0.5 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 1N hydrochloride, a saturated solution of sodium carbonate, 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=1/2) to give 3.0 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 1N hydrochloride
  4. dry with materiala saturated solution of sodium carbonate, 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=1/2)

Sources & evidence

ORD record
ord-1aa03bdaa1d54c32b0048e7aefd7e21b
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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