Benzenesulfonyl chloride → 5-Isobutyl-1-phenyl-3-(3-benzenesulfonyl-3-azabicyclo[3.1.0]hexane-6-carboxamido)methyl-1H-pyrazole

HRID 340750Notes

Reaction equation

HRID 340750 reaction equation
Cl.[CH2:2]([C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[C:8]([CH2:17][NH:18][C:19]([CH:21]2[CH:26]3[CH:22]2[CH2:23][NH:24][CH2:25]3)=[O:20])[CH:7]=1)[CH:3]([CH3:5])[CH3:4].C(N(CC)CC)C.[C:34]1([S:40](Cl)(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CCCCCC>C(Cl)Cl.C(OCC)(=O)C>[CH2:2]([C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[C:8]([CH2:17][NH:18][C:19]([CH:21]2[CH:26]3[CH:22]2[CH2:23][N:24]([S:40]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:42])=[O:41])[CH2:25]3)=[O:20])[CH:7]=1)[CH:3]([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8058HexaneHCID 8471TriethylamineHCID 1177004486-((5-Isobutyl-1-phenyl-1H-pyrazole-3-yl)methylcarbamoyl)-3-azabicyclo[3.1.0]hexane hydrochloride

Product 1

HCID 862927515-Isobutyl-1-phenyl-3-(3-benzenesulfonyl-3-azabicyclo[3.1.0]hexane-6-carboxamido)methyl-1H-pyrazoleYield 79.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 6-((5-isobutyl-1-phenyl-1H-pyrazole-3-yl)methylcarbamoyl)-3-azabicyclo[3.1.0]hexane hydrochloride (69.5 mg, 0.185 mmol) prepared in Example 11 was dissolved in 2.0 mL of methylene chloride and triethylamine (54.3 μL, 0.389 mmol) was added dropwise at 0° C. After stirring for 5 minutes, benzenesulfonyl chloride (24.9 μL, 0.195 mmol) was added dropwise. 10 minutes later, after stirring at room temperature for 1 hour, the completion of the reaction was confirmed by TLC (hexane:ethyl acetate=1:2). After the reaction was completed, the reaction mixture was extracted with methylene chloride after adding water and saturated sodium bicarbonate. The organic layer was dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and separated by column chromatography (hexane:ethyl acetate=1:1→1:2) to obtain 70.4 mg (79.4%) of the target compound.

Workup

  1. stirring10 minutes later, after stirring at room temperature for 1 hour
  2. extractionthe reaction mixture was extracted with methylene chloride
  3. additionafter adding water and saturated sodium bicarbonate
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customseparated by column chromatography (hexane:ethyl acetate=1:1→1:2)

Sources & evidence

ORD record
ord-0c154b28ae0c4ca7861720d4107d7e53
Source dataset
uspto-grants-2014_11
Patent number
US08895602B1

Reaction notes

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