Trimethylaluminum → 5-[(4S,5R)-4,5-bis(4-chlorophenyl)-4,5-dimethyl-1H-imidazol-2-yl]-2-tert-butyl-4-ethoxy-N,N-dimethylbenzenesulfonamide

HRID 2263894Notes

Reaction equation

HRID 2263894 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:34])[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)([CH3:13])[NH:11][C:10]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][C:22]=3[O:31][CH2:32][CH3:33])=[N:9]2)=[CH:4][CH:3]=1.COC(=O)C1C=C([S:44](=[O:49])(=[O:48])[N:45]([CH3:47])[CH3:46])C(C(C)(C)C)=CC=1OCC.C[Al](C)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@:8]2([CH3:34])[C@:12]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([CH3:13])[NH:11][C:10]([C:21]3[C:22]([O:31][CH2:32][CH3:33])=[CH:23][C:24]([C:27]([CH3:28])([CH3:30])[CH3:29])=[C:25]([S:44]([N:45]([CH3:47])[CH3:46])(=[O:49])=[O:48])[CH:26]=3)=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 16682925TrimethylaluminumHCID 53628801rac-(4S*,5R*)-2-(4-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazoleHCID 670716004-Tert-butyl-5-dimethylsulfamoyl-2-ethoxy-benzoic acid methyl ester

Product 1

HCID 686842965-[(4S,5R)-4,5-bis(4-chlorophenyl)-4,5-dimethyl-1H-imidazol-2-yl]-2-tert-butyl-4-ethoxy-N,N-dimethylbenzenesulfonamide

Procedure

In a manner analogous to the method described in example 2, meso-2,3-bis-(4-chlorophenyl)-2,3-butanediamine (example 1) was reacted with 4-tert-butyl-5-dimethylsulfamoyl-2-ethoxy-benzoic acid methyl ester (prepared in an analogous manner as described in example 43) in the presence of trimethylaluminum to give rac-5-[(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-2-tert-butyl-4-ethoxy-N,N-dimethyl-benzenesulfonamide.

Workup

  1. customprepared in an analogous manner

Sources & evidence

ORD record
ord-7db64641b28e45b6b2fa021a51853ff9
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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