2-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-2-yl-ethyl)-amide

HRID 1359772Notes

Reaction equation

HRID 1359772 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.[N:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[CH2:49][CH2:50][NH2:51]>CC(N(C)C)=O>[N:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[CH2:49][CH2:50][NH:51][C:11]([C:13]1[C:17]([CH3:18])=[C:16](/[CH:19]=[C:20]2\[C:21](=[O:41])[NH:22][C:23]3[C:28]\2=[CH:27][C:26]([S:29]([CH2:32][C:33]2[C:34]([Cl:40])=[CH:35][CH:36]=[CH:37][C:38]=2[Cl:39])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[NH:15][C:14]=1[CH3:42])=[O:12]

Participants

4

Reactant 2

HCID 759192-PyridineethanamineHCID 137178925HCID 137178925, compound

Product 1

HCID 590775405-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-Pyridin-2-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-2-yl-ethylamine (39 mg, 2 eq.). The mixture was stirred at rt for 3 days. The reaction was concentrated, diluted with DCM, washed with sat. NaHCO3 and 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 with sat. NaHCO3 and water
  4. concentrationconcentrated
  5. customtriturated with methanol

Sources & evidence

ORD record
ord-1153b21ddb9b4c039b21f4a9246eb5fb
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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