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

HRID 1359774Notes

Reaction equation

HRID 1359774 reaction equation
N1C2C(=NC=CC=2)N([O:10][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)N=1.[N:43]1[CH:48]=[CH:47][C:46]([CH2:49][CH2:50][NH2:51])=[CH:45][CH:44]=1>CC(N(C)C)=O>[N:43]1[CH:48]=[CH:47][C:46]([CH2:49][CH2:50][NH:51][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:10])=[CH:45][CH:44]=1

Participants

4

Reactant 2

HCID 832754-PyridineethanamineHCID 137178925HCID 137178925, compound

Product 1

HCID 590777425-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-Pyridin-4-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 2-pyridin-4-yl-ethylamine (39 mg, 2 eq.). The mixture was stirred at rt for 18 hours. The reaction was concentrated, diluted with DCM, washed with sat. NaHCO3 and water, concentrated and triturated with ethanol to give the titled compound as a yellow solid.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with DCM
  3. washwashed with sat. NaHCO3 and water
  4. concentrationconcentrated
  5. customtriturated with ethanol

Sources & evidence

ORD record
ord-5f67169db23647708dd2901d5c0266de
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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