Acryloyl chloride → N-[4-(2-Morpholin-4-yl-ethylsulfamoyl)-phenyl]-acrylamide

HRID 1841952

Reaction equation

HRID 1841952 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[C:29](Cl)(=[O:32])[CH:30]=[CH2:31]>C1COCC1>[N:23]1([CH2:22][CH2:21][NH:20][S:17]([C:14]2[CH:13]=[CH:12][C:11]([NH:10][C:29](=[O:32])[CH:30]=[CH2:31])=[CH:16][CH:15]=2)(=[O:19])=[O:18])[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 120569Benzenesulfonamide, 4-amino-N-[2-(4-morpholinyl)ethyl]-

Product 1

HCID 67194942N-[4-(2-Morpholin-4-yl-ethylsulfamoyl)-phenyl]-acrylamideYield 5.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (0.09 ml, 0.5 mmol) was added in one portion to a stirred solution of 4-amino-N-(2-morpholin-4-yl-ethyl)-benzenesulfonamide (0.1 g, 0.35 mmol) in THF (3 ml) at room temperature. To this mixture was added acryloyl chloride (0.03 ml, 0.38 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After this time, the mixture was concentrated under vacuum and the resulting residue purified by Prep HPLC to give the title compound (6 mg, 5% yield) as a white solid.

Workup

  1. concentrationAfter this time, the mixture was concentrated under vacuum
  2. customthe resulting residue purified by Prep HPLC

Sources & evidence

ORD record
ord-fbc6602e838844ea8049e8f1cc4695df
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Linked notes

Loading…