1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-Cyclopropyl-N-[1-(6-oxo-1,6-dihydro-pyridine-3-carbonyl)-piperidin-4-yl]-3-trifluoromethyl-benzenesulfonamide

HRID 1428958Notes

Reaction equation

HRID 1428958 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.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[OH:45][C:46]1[CH:54]=[CH:53][C:49]([C:50](O)=[O:51])=[CH:48][N:47]=1>CN(C=O)C>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([C:50]([C:49]3[CH:53]=[CH:54][C:46](=[O:45])[NH:47][CH:48]=3)=[O:51])[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 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2773944N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamideHCID 178418479HCID 178418479, compound

Product 1

HCID 24860754N-Cyclopropyl-N-[1-(6-oxo-1,6-dihydro-pyridine-3-carbonyl)-piperidin-4-yl]-3-trifluoromethyl-benzenesulfonamideYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Cyclopropyl-N-piperidin-4-yl-3-trifluoromethyl-benzenesulfonamide (0.174 g, 0.50 mmol), HOBt (0.068 g, 0.50 mmol), EDCI (0.115 g, 0.60 mmol) and 6-hydroxynicotinoic acid (0.078 g, 0.55 mmol) were dissolved in 5 ml of dry DMF. The mixture allowed to stir at room temperature for 10 hours. The reaction mixture was concentrated and dried under reduced pressure. Then residue was dissolved in EtOAc (30 ml) and the mixture was washed with saturated NaHCO3 (15 ml) and brine (15 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 5% to 10% MeOH in CHCl3 to afford the title compound 6 (colorless solid, 195 mg, 83%). LC: 100%. MS: m/z=469.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried under reduced pressure
  3. dissolutionThen residue was dissolved in EtOAc (30 ml)
  4. washthe mixture was washed with saturated NaHCO3 (15 ml) and brine (15 ml)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified through a column of silica gel with a gradient of 5% to 10% MeOH in CHCl3

Sources & evidence

ORD record
ord-f023f103d33740af92f4332923e79bbf
Source dataset
uspto-grants-2015_01
Patent number
US08937181B2

Reaction notes

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