Dimethylformamide → N-Cyclopropyl-N-[1-(2-nitro-benzoyl)-piperidin-4-yl]-3-trifluoromethyl-benzenesulfonamide

HRID 1428960

Reaction equation

HRID 1428960 reaction equation
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[CH:24]1[CH:25]=[CH:26][C:27]2[N:32]([OH:33])N=N[C:28]=2[CH:29]=1.CCN=C=NCCCN(C)C.[N+]([O:48][C:49](=O)C1C=CC=CC=1)([O-])=O.CN(C=[O:61])C>>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([C:49](=[O:48])[C:28]3[CH:29]=[CH:24][CH:25]=[CH:26][C:27]=3[N+:32]([O-:33])=[O:61])[CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)(=[O:6])=[O:7])[CH2:3][CH2:2]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2773944N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamideHCID 12282512Nitro benzoate

Product 1

HCID 24860818N-Cyclopropyl-N-[1-(2-nitro-benzoyl)-piperidin-4-yl]-3-trifluoromethyl-benzenesulfonamideYield 93%

Procedure

N-Cyclopropyl-N-piperidin-4-yl-3-trifluoromethyl-benzenesulfonamide (0.348 g, 1.0 mmol), HOBt (0.135 g, 1.0 mmol), EDCI (0.230 g, 1.2 mmol) and O-nitrobenzoic acid (0.184 g, 1.1 mmol) were dissolved in 10 ml of dry DMF. The mixture was allowed to stir at room temperature for 16 hours. The reaction mixture was concentrated and dryness under reduced pressure. Then the residue was dissolved in EtOAc (50 ml) and the mixture was washed with saturated NaHCO3 (30 ml) and brine (30 ml). The organic layer was dried over MgSO4 and concentrated to dryness. The crude product was purified through a column of silica gel with a gradient of 65% to 80% EtOAc in hexane to afford the title compound 10 (pale yellow solid, 462 mg, 93%). LC: 97%. MS: m/z=497.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThen the residue was dissolved in EtOAc (50 ml)
  3. washthe mixture was washed with saturated NaHCO3 (30 ml) and brine (30 ml)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified through a column of silica gel with a gradient of 65% to 80% EtOAc in hexane

Sources & evidence

ORD record
ord-c189aa789d4b4f5a9fdc59bc8325994a
Source dataset
uspto-grants-2015_01
Patent number
US08937181B2

Linked notes

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