Potassium Iodide → methyl (S)-2-(4-methanesulfonylpiperazin-1-yl)-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]propanoate

HRID 472125Notes

Reaction equation

HRID 472125 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH3:19])[CH:10]=1.[I-].[K+].[OH:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:32][CH2:33][C@H:34]([N:39]2[CH2:44][CH2:43][N:42]([S:45]([CH3:48])(=[O:47])=[O:46])[CH2:41][CH2:40]2)[C:35]([O:37][CH3:38])=[O:36])(=[O:31])=[O:30])=[CH:25][CH:24]=1>CC(C)=O>[CH3:48][S:45]([N:42]1[CH2:41][CH2:40][N:39]([C@@H:34]([CH2:33][NH:32][S:29]([C:26]2[CH:25]=[CH:24][C:23]([O:22][CH2:8][C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=[C:11]([CH3:19])[CH:10]=3)=[CH:28][CH:27]=2)(=[O:31])=[O:30])[C:35]([O:37][CH3:38])=[O:36])[CH2:44][CH2:43]1)(=[O:46])=[O:47]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 115357194-(Chloromethyl)-2-methylquinolineHCID 86675015methyl (S)-3-(4-hydroxybenzenesulfonylamino)-2-(4-methanesulfonylpiperazin-1-yl)propanoate

Product 1

HCID 86675016methyl (S)-2-(4-methanesulfonylpiperazin-1-yl)-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]propanoateYield 32%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

280 mg (0.85 mmol) of cesium carbonate followed by 160 mg (0.85 mmol) of 4-chloromethyl-2-methylquinoline and by 15 mg of potassium iodide are added to a solution of 300 mg (0.71 mmol) of methyl (S)-3-(4-hydroxybenzenesulfonylamino)-2-(4-methanesulfonylpiperazin-1-yl)propanoate in 10 ml of acetone. The reaction medium is stirred at ambient temperature for 18 h, filtered and concentrated under vacuum. The crude product is purified by chromatography on silica gel, elution being carried out with a 40/60 heptane/ethyl acetate mixture. 130 mg (32%) of methyl (S)-2-(4-methanesulfonylpiperazin-1-yl)-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]propanoate are obtained in the form of a white solid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under vacuum
  3. customThe crude product is purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-5f1b73cb439b425697bce62a96de3006
Source dataset
uspto-grants-2014_01
Patent number
US08633196B2

Reaction notes

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