1-(6-Methylpyridin-2-yl)piperazine → 5-Cyano-1-(2,4-dimethoxybenzenesulfonyl)-3-(2-ethoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(6-methylpyridin-2-yl)piperazine-1-carboxylate

HRID 1091549Notes

Reaction equation

HRID 1091549 reaction equation
[C:1](=O)([O:37]C1C=CC=CC=1)[O:2][C:3]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH2:35][CH3:36])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])(=[O:16])=[O:15])[C:4]1=[O:27].[CH3:45][C:46]1[N:51]=[C:50]([N:52]2[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]2)[CH:49]=[CH:48][CH:47]=1>CN(C=O)C>[CH3:45][C:46]1[N:51]=[C:50]([N:52]2[CH2:57][CH2:56][N:55]([C:1]([O:2][C:3]3([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH2:35][CH3:36])[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=4)[N:5]([S:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=4[O:25][CH3:26])(=[O:16])=[O:15])[C:4]3=[O:27])=[O:37])[CH2:54][CH2:53]2)[CH:49]=[CH:48][CH:47]=1

Participants

4

Reactant 2

HCID 27369461-(6-Methylpyridin-2-yl)piperazineHCID 866328045-Cyano-1-(2,4-dimethoxybenzenesulfonyl)-3-(2-ethoxyphenyl)-2-oxo-2,3-dihydro-1-H-indol-3-yl phenyl carbonate

Product 1

HCID 118476875-Cyano-1-(2,4-dimethoxybenzenesulfonyl)-3-(2-ethoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(6-methylpyridin-2-yl)piperazine-1-carboxylateYield 89.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.1 g (0.16 mmol) of intermediate 1d and 115 mg (0.65 mmol) of 1-(6-methylpyridin-2-yl)piperazine were stirred in 3 ml of DMF at 100° C. for 20 minutes. The reaction mixture was then poured into 30 ml of ice-water/K2CO3. The resulting precipitate was isolated and crystallized from a little methanol, resulting 0.1 g of the product.

Workup

  1. customThe resulting precipitate was isolated
  2. customcrystallized from a little methanol

Sources & evidence

ORD record
ord-fdcc708212f844d6804c2c3d4b085c48
Source dataset
uspto-grants-2012_03
Patent number
US08129389B2

Reaction notes

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