Triethylamine → Dimethyl 2-[(4-but-2-ynyloxybenzoylamino)methyl]-2-(4-methanesulphonylpiperazin-1-yl)malonate

HRID 517490Notes

Reaction equation

HRID 517490 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].C(OC([N:20]1[CH2:25][CH2:24][N:23]([C:26]([CH2:35][NH:36][C:37](=[O:49])[C:38]2[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]#[C:47][CH3:48])=[CH:40][CH:39]=2)([C:31]([O:33][CH3:34])=[O:32])[C:27]([O:29][CH3:30])=[O:28])[CH2:22][CH2:21]1)=O)(C)(C)C>ClCCl>[CH2:45]([O:44][C:41]1[CH:40]=[CH:39][C:38]([C:37]([NH:36][CH2:35][C:26]([N:23]2[CH2:24][CH2:25][N:20]([S:9]([CH3:8])(=[O:11])=[O:10])[CH2:21][CH2:22]2)([C:27]([O:29][CH3:30])=[O:28])[C:31]([O:33][CH3:34])=[O:32])=[O:49])=[CH:43][CH:42]=1)[C:46]#[C:47][CH3:48]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67056950Dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)-2-[(4-but-2-ynyloxybenzoylamino)methyl]malonate

Product 1

HCID 67056992Dimethyl 2-[(4-but-2-ynyloxybenzoylamino)methyl]-2-(4-methanesulphonylpiperazin-1-yl)malonateYield 112.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.8 ml (5.7 mmol) of triethylamine then 0.4 ml (5.7 mmol) of methanesulphonyl chloride are added to a solution of 2.2 g (3.6 mmol) of dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)-2-[(4-but-2-ynyloxybenzoylamino)methyl]malonate in 25 ml of dichloromethane. The reaction medium is then stirred at ambient temperature for 3 h, then the solvents are evaporated under vacuum and the crude product obtained is purified by chromatography over silica gel eluted with a 98/2 dichloromethane/methanol mixture. 2 g (80%) of dimethyl 2-[(4-but-2-ynyloxybenzoylamino)methyl]-2-(4-methane-sulphonylpiperazin-1-yl)malonate are obtained in the form of a white solid.

Workup

  1. customthe solvents are evaporated under vacuum
  2. customthe crude product obtained
  3. customis purified by chromatography over silica gel
  4. washeluted with a 98/2 dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-5699e4ec30b4431284ab88d3b5d18258
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

Loading…