Triethylamine → HCID 118432166, compound

HRID 2207997Notes

Reaction equation

HRID 2207997 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]3[CH2:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:15]=2)[CH2:12][C:11]([C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])=[N:10]1.C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>ClCCl>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]3[CH2:26][CH2:25][CH2:24][N:23]([S:42]([CH3:41])(=[O:44])=[O:43])[CH2:22][CH2:21]3)[CH:15]=2)[CH2:12][C:11]([C:27]([F:33])([F:32])[C:28]([F:30])([F:31])[F:29])=[N:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 118431760HCID 118431760, compound

Product 1

HCID 118432166HCID 118432166, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Chloro-phenyl)-5-[3-(homopiperazin-1-yl)-phenyl]-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole hydrochloride (30.0 mg, 0.06 mmol) prepared in Step 1, triethylamine (41.0 uL, 0.30 mmol) and methanesulfonyl chloride (8.1 mg, 0.07 mmol) were added to dichloromethane (1.0 mL). The reaction mixture was stirred at room temperature for 3 hours, washed with distilled water, 1N hydrochloride, a saturated solution of sodium hydrogen 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 3.4 mg of the titled compound as a yellow liquid.

Workup

  1. washwashed with distilled water, 1N hydrochloride
  2. dry with materiala saturated solution of sodium hydrogen carbonate, and brine, dried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a yellow liquid residue
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2)

Sources & evidence

ORD record
ord-e474b6fa5951485395f11ffe202b4fc9
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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