Dichloromethane → HCID 118431731, compound

HRID 2208085Notes

Reaction equation

HRID 2208085 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][C:24]([C:27]3[CH2:28][CH2:29][NH:30][CH2:31][CH:32]=3)=[CH:23][CH:22]=2)[CH2:19][C:18]([C:33]([C:39]([F:42])([F:41])[F:40])([C:35]([F:38])([F:37])[F:36])[OH:34])=[N:17]1.C(N(CC)CC)C.[CH3:50][S:51](Cl)(=[O:53])=[O:52].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][C:24]([C:27]3[CH2:28][CH2:29][N:30]([S:51]([CH3:50])(=[O:53])=[O:52])[CH2:31][CH:32]=3)=[CH:23][CH:22]=2)[CH2:19][C:18]([C:33]([C:39]([F:40])([F:41])[F:42])([C:35]([F:36])([F:37])[F:38])[OH:34])=[N:17]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 118432039HCID 118432039, compound

Product 1

HCID 118431731HCID 118431731, compoundYield 7.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(2,4-Difluoro-phenyl)-5-[4-(1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole trifluoroacetate (30.0 mg, 0.05 mmol) prepared in Example 399, triethylamine (20.3 uL, 0.15 mmol) and methanesulfonyl chloride (4.6 uL, 0.06 mmol) were added at 0° C. to dichloromethane (1.0 mL). The reaction mixture was stirred at room temperature for 12 hours and then distilled water was added thereto. The reaction mixture was extracted with dichloromethane two times. The combined extract was washed with a 1N hydrochloric acid solution, 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=1/3) to give 2.1 mg of the titled compound as a yellow liquid.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane two times
  2. extractionThe combined extract
  3. washwas washed with a 1N hydrochloric acid solution
  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=1/3)

Sources & evidence

ORD record
ord-eed0b071a53244c4822f05da68c631df
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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