2-Bromopropane → [5-(4-Cyclopentyl-piperazine-1-carbonyl)-1-isopropyl-1H-indol-2-yl]-(1,1-dioxo-thiomorpholin-4-yl)-methanone

HRID 1820422Notes

Reaction equation

HRID 1820422 reaction equation
[CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[NH:19][C:18]([C:23]([N:25]3[CH2:30][CH2:29][S:28](=[O:32])(=[O:31])[CH2:27][CH2:26]3)=[O:24])=[CH:17]4)=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH:36]([CH3:38])[CH3:37]>CN(C)C=O>[CH:1]1([N:6]2[CH2:7][CH2:8][N:9]([C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19]([CH:36]([CH3:38])[CH3:37])[C:18]([C:23]([N:25]3[CH2:30][CH2:29][S:28](=[O:31])(=[O:32])[CH2:27][CH2:26]3)=[O:24])=[CH:17]4)=[O:13])[CH2:10][CH2:11]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 68680722[5-(4-Cyclopentyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(1,1-dioxo-thiomorpholin-4-yl)-methanone

Product 1

HCID 68682430[5-(4-Cyclopentyl-piperazine-1-carbonyl)-1-isopropyl-1H-indol-2-yl]-(1,1-dioxo-thiomorpholin-4-yl)-methanoneYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in analogy to example 51, from [5-(4-cyclopentyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(1,1-dioxo-thiomorpholin-4-yl)-methanone (example 34), sodium hydride and 2-bromopropane in N,N-dimethylformamide, to give the desired product as a light yellow foam (33%).

Sources & evidence

ORD record
ord-1023e071daa249fd8da2b8404328d140
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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