1-[4-(2-Aminoethyl)piperazin-1-yl]ethan-1-one → 5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid [2-(4-acetyl-piperazin-1-yl)-ethyl]-amide

HRID 1359787Notes

Reaction equation

HRID 1359787 reaction equation
N1C2C(=NC=CC=2)N(O[C:11]([C:13]2[C:17]([CH3:18])=[C:16](/[CH:19]=[C:20]3\[C:21](=[O:41])[NH:22][C:23]4[C:28]\3=[CH:27][C:26]([S:29]([CH2:32][C:33]3[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:40])(=[O:31])=[O:30])=[CH:25][CH:24]=4)[NH:15][C:14]=2[CH3:42])=[O:12])N=1.[NH2:43][CH2:44][CH2:45][N:46]1[CH2:51][CH2:50][N:49]([C:52](=[O:54])[CH3:53])[CH2:48][CH2:47]1>CC(N(C)C)=O>[C:52]([N:49]1[CH2:50][CH2:51][N:46]([CH2:45][CH2:44][NH:43][C:11]([C:13]2[C:17]([CH3:18])=[C:16](/[CH:19]=[C:20]3\[C:21](=[O:41])[NH:22][C:23]4[C:28]\3=[CH:27][C:26]([S:29]([CH2:32][C:33]3[C:34]([Cl:40])=[CH:35][CH:36]=[CH:37][C:38]=3[Cl:39])(=[O:31])=[O:30])=[CH:25][CH:24]=4)[NH:15][C:14]=2[CH3:42])=[O:12])[CH2:47][CH2:48]1)(=[O:54])[CH3:53]

Participants

4

Reactant 2

HCID 167857031-[4-(2-Aminoethyl)piperazin-1-yl]ethan-1-oneHCID 137178925HCID 137178925, compound

Product 1

HCID 590774675-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid [2-(4-acetyl-piperazin-1-yl)-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid [1,2,3]triazolo[4,5-b]pyridin-3-yl ester (100 mg, 0.162 mmol) in DMA (2 mL) was added 1-[4-(2-amino-ethyl)-piperazin-1-yl]-ethanone (55 mg, 2 eq.). The mixture was stirred at rt for 2 hours. The reaction was concentrated, diluted with DCM, washed with sat.NaHCO3, water, concentrated and triturated with methanol to give the titled compound as a yellow solid.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with DCM
  3. washwashed
  4. concentrationNaHCO3, water, concentrated
  5. customtriturated with methanol

Sources & evidence

ORD record
ord-15696fff4c944476ac16900bfc225d5e
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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