Sodium hydride → (RS)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(3,3,3-trifluoro-propane-1-sulfonyl)-imidazolidin-2-one

HRID 1864409Notes

Reaction equation

HRID 1864409 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([CH:17]2[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:20](=[O:28])[NH:19][CH2:18]2)=[O:16])[CH2:11][CH2:10]1.[H-].[Na+].[F:31][C:32]([F:40])([F:39])[CH2:33][CH2:34][S:35](Cl)(=[O:37])=[O:36]>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([CH:17]2[CH2:18][N:19]([S:35]([CH2:34][CH2:33][C:32]([F:40])([F:39])[F:31])(=[O:37])=[O:36])[C:20](=[O:28])[N:21]2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:16])[CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 27611773,3,3-Trifluoropropane-1-sulfonyl chlorideHCID 67142096(RS)-5-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-1-phenyl-imidazolidin-2-one

Product 1

HCID 25029060(RS)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(3,3,3-trifluoro-propane-1-sulfonyl)-imidazolidin-2-one

Procedure

In analogy to example 33, (RS)-5-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-1-phenyl-imidazolidin-2-one (example 33, step 1) was reacted with sodium hydride and 3,3,3-trifluoropropane-1-sulfonyl chloride to give the title compound as an off-white solid. MS: 539.0 ([M+H]+)

Sources & evidence

ORD record
ord-6df53e9315954e87a3d35d9ff4bb07dc
Source dataset
uspto-grants-2009_12
Patent number
US07625902B2

Reaction notes

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