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

HRID 2043072Notes

Reaction equation

HRID 2043072 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+].[CH3:31][N:32]=[C:33]=[S:34]>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:33]([NH:32][CH3:31])=[S:34])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:8]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11167Methyl isothiocyanateHCID 122820304-(2-(5-Chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide

Product 1

HCID 115832125-Chloro-2-methoxy-N-(2-(1-(3-methylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamideYield 20%

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 mmol) of cesium carbonate were heated in 5 ml of N-methyl-2-pyrrolidone with 73 mg (1 mmol) of methyl 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 and washed with water until neutral. Purification by chromatography (silica gel; toluene/ethanol/ethyl acetate 8/1/1) resulted in 90 mg (20%) of the title compound 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. customPurification by chromatography (silica gel; toluene/ethanol/ethyl acetate 8/1/1)

Sources & evidence

ORD record
ord-5ac36e43e25349d181d6e07bdedfc22d
Source dataset
uspto-grants-2013_11
Patent number
US08586612B2

Reaction notes

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