Triethylamine → HCID 118432052, compound

HRID 2208030Notes

Reaction equation

HRID 2208030 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[S:22][C:23]([C:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=3)=[CH:24][CH:25]=2)[CH2:19][C:18]([C:32]([F:38])([F:37])[C:33]([F:36])([F:35])[F:34])=[N:17]1.C(N(CC)CC)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48]>ClCCl>[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[S: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)[CH2:19][C:18]([C:32]([F:37])([F:38])[C:33]([F:35])([F:36])[F:34])=[N:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 118431668HCID 118431668, compound

Product 1

HCID 118432052HCID 118432052, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2,4-Difluoro-phenyl)-5-[5-(1,2,3,6-tetrahydropyridin-4-yl)-thiophen-2-yl]-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole trifluoroacetate (27.0 mg, 0.05 mmol) prepared in Step 1, triethylamine (32.5 uL, 0.23 mmol) and methanesulfonyl chloride (8.0 mg, 0.07 mmol) were added to dichloromethane (1.0 mL). The reaction mixture was stirred at room temperature for 18 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=2/1) to give 5.0 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=2/1)

Sources & evidence

ORD record
ord-7399fdde3e1a405a87daf99ef8cd63c1
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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