Triethylamine → Dimethyl 2-[(4-but-2-ynyloxybenzenesulfonylamino)methyl]-2-(4-methanesulfonylpiperazin-1-yl)malonate

HRID 1966092Notes

Reaction equation

HRID 1966092 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[CH2:13]([O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][CH2:28][C:29]([N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)([C:34]([O:36][CH3:37])=[O:35])[C:30]([O:32][CH3:33])=[O:31])(=[O:26])=[O:25])=[CH:20][CH:19]=1)[C:14]#[C:15][CH3:16]>ClCCl>[CH2:13]([O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][CH2:28][C:29]([N:38]2[CH2:39][CH2:40][N:41]([S:9]([CH3:8])(=[O:11])=[O:10])[CH2:42][CH2:43]2)([C:30]([O:32][CH3:33])=[O:31])[C:34]([O:36][CH3:37])=[O:35])(=[O:26])=[O:25])=[CH:20][CH:19]=1)[C:14]#[C:15][CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 71115173Dimethyl 2-[(4-but-2-ynyloxybenzenesulfonylamino)methyl]-2-piperazin-1-ylmalonate

Product 1

HCID 71115264Dimethyl 2-[(4-but-2-ynyloxybenzenesulfonylamino)methyl]-2-(4-methanesulfonylpiperazin-1-yl)malonateYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.6 ml (4 mmol) of triethylamine and then 0.3 ml (4 mmol) of methanesulfonyl chloride are added to a solution of 1.6 g (4 mmol) of dimethyl 2-[(4-but-2-ynyloxybenzenesulfonylamino)methyl]-2-piperazin-1-ylmalonate diluted in 30 ml of dichloromethane. The reaction medium is then stirred at ambient temperature for 3 h and then evaporated to dryness. The crude residue is purified by chromatography on silica gel, elution being carried out with a 99/1 dichloromethane/methanol mixture. 1.1 g (58%) of dimethyl 2-[(4-but-2-ynyloxybenzenesulfonylamino)methyl]-2-(4-methanesulfonylpiperazin-1-yl)malonate are obtained in the form of a white solid.

Workup

  1. customevaporated to dryness
  2. customThe crude residue is purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-04a9308ef7d9477484322326692bfa9d
Source dataset
uspto-grants-2013_04
Patent number
US08420632B2

Reaction notes

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