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

HRID 2043075Notes

Reaction equation

HRID 2043075 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+].[CH:31]([N:34]=[C:35]=[S:36])([CH3:33])[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:35]([NH:34][CH:31]([CH3:33])[CH3:32])=[S:36])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:8]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 75263Isopropyl IsothiocyanateHCID 122820304-(2-(5-Chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide

Product 1

HCID 115185565-Chloro-2-methoxy-N-(2-(1-(3-isopropylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamideYield 60%

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 (0.9 mmol) of isopropyl 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 dried over sodium sulfate and filtered after addition of activated carbon. The crude product obtained after removal of the solvent was recrystallized from methanol. 142 mg (60%) 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. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. additionafter addition of activated carbon
  6. customThe crude product obtained
  7. customafter removal of the solvent
  8. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-d9484b6b11754664b874ae0ba8078f6f
Source dataset
uspto-grants-2013_11
Patent number
US08586612B2

Reaction notes

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