Cesium carbonate → 5-Chloro-2-methoxy-N-(2-(1-(3-ethylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamide

HRID 2043073Notes

Reaction equation

HRID 2043073 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([S:18]([NH2:21])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:31]([N:33]=[C:34]=[S:35])[CH3:32]>CN1CCCC1=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([S:18]([NH:21][C:34]([NH:33][CH2:31][CH3:32])=[S:35])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:8]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 10966Ethyl isothiocyanateHCID 122820304-(2-(5-Chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide

Product 1

HCID 596607115-Chloro-2-methoxy-N-(2-(1-(3-ethylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamideYield 35%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

188 mg (0.5 mmol) of 4-(2-(5-chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide and 326 mg (1 mmol) of cesium carbonate were heated in 5 ml of N-methyl-2-pyrrolidone with 0.1 ml (1.1 mmol) of ethyl isothiocyanate at 80° C. for 10 minutes. The reaction mixture was poured onto ice/2 M hydrochloric acid and extracted three times with 10 ml of dichloromethane each time. The combined organic phases were washed with water until neutral, dried over sodium sulfate and filtered after addition of activated carbon. The crude product obtained after removal of the solvent was recrystallized from methanol/water. 80 mg (35%) of the title compound were obtained as a colorless solid.

Workup

  1. additionThe reaction mixture was poured onto ice/2 M hydrochloric acid
  2. extractionextracted three times with 10 ml of dichloromethane each time
  3. washThe combined organic phases were washed with water until neutral,
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. additionafter addition of activated carbon
  7. customThe crude product obtained
  8. customafter removal of the solvent
  9. customwas recrystallized from methanol/water

Sources & evidence

ORD record
ord-d84013f604c74a7ea4da4637f7eaec1e
Source dataset
uspto-grants-2013_11
Patent number
US08586612B2

Reaction notes

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