Triethylamine → HCID 118432007, compound

HRID 2208065Notes

Reaction equation

HRID 2208065 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][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[CH2:12][C:11]([C:27]([C:33]([F:36])([F:35])[F:34])([C:29]([F:32])([F:31])[F:30])[OH:28])=[N:10]1.C(N(CC)CC)C.[CH:44]1([S:47](Cl)(=[O:49])=[O:48])[CH2:46][CH2:45]1>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][C:17]([N:20]3[CH2:21][CH2:22][CH:23]([NH:26][S:47]([CH:44]4[CH2:46][CH2:45]4)(=[O:49])=[O:48])[CH2:24][CH2:25]3)=[CH:16][CH:15]=2)[CH2:12][C:11]([C:27]([C:33]([F:36])([F:34])[F:35])([C:29]([F:31])([F:30])[F:32])[OH:28])=[N:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 118431917HCID 118431917, compound

Product 1

HCID 118432007HCID 118432007, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Chloro-phenyl)-5-{4-[4-amino-piperidin-1-yl]-phenyl}-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole hydrochloride (30.0 mg, 0.06 mmol) prepared in Example 331, triethylamine (37.3 uL, 0.27 mmol) and cyclopropanesulfonyl chloride (10.4 mg, 0.08 mmol) were added to dichloromethane (1.0 mL). The reaction mixture was stirred at room temperature for 1 hour, 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 10.0 mg of the titled compound as a pale 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-592061f13f874a7ab9a681b8e1175774
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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