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

HRID 2043077

Reaction equation

HRID 2043077 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]1([N:37]=[C:38]=[S:39])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>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:38]([NH:37][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[S:39])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:8]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 14289Cyclohexyl isothiocyanateHCID 122820304-(2-(5-Chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide

Product 1

HCID 596607125-Chloro-2-methoxy-N-(2-(1-(3-cyclohexylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamideYield 45%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

376 mg (1 mmol) of 4-(2-(5-chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide and 652 mg (2.0 mmol) of cesium carbonate were heated in 5 ml of N-methyl-2-pyrrolidone with 0.3 ml (2 mmol) of cyclohexyl isothiocyanate at 80° C. for 10 minutes. The reaction mixture was poured onto ice/2 M hydrochloric acid, and the precipitated solid was filtered off with suction, washed with water until neutral, dissolved in methanol, filtered after addition of activated carbon and crystallized using diethyl ether. 230 mg (45%) of the title compound were obtained as a colorless solid.

Workup

  1. additionThe reaction mixture was poured onto ice/2 M hydrochloric acid
  2. filtrationthe precipitated solid was filtered off with suction
  3. washwashed with water until neutral,
  4. dissolutiondissolved in methanol
  5. filtrationfiltered
  6. additionafter addition of activated carbon
  7. customcrystallized

Sources & evidence

ORD record
ord-f9818bdd00444776a8546114a0618c35
Source dataset
uspto-grants-2013_11
Patent number
US08586612B2

Linked notes

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