Trimethylaluminum → rac-(4S*,5R*)-5-[4,5-Bis-(4-chlorophenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-N-tert-butyl-2-chloro-4-ethoxybenzenesulfonamide

HRID 2263927Notes

Reaction equation

HRID 2263927 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(C3C=CC(C(C)(C)C)=CC=3OCC)=[N:9]2)=[CH:4][CH:3]=1.CO[C:37](=O)[C:38]1[CH:43]=[C:42]([S:44](=[O:51])(=[O:50])[NH:45][C:46]([CH3:49])([CH3:48])[CH3:47])[C:41]([Cl:52])=[CH:40][C:39]=1[O:53][CH2:54][CH3:55].C[Al](C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][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:37]([C:38]3[C:39]([O:53][CH2:54][CH3:55])=[CH:40][C:41]([Cl:52])=[C:42]([S:44]([NH:45][C:46]([CH3:49])([CH3:48])[CH3:47])(=[O:51])=[O:50])[CH:43]=3)=[N:9]2)=[CH:4][CH:3]=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 588942525-Tert-butylsulfamoyl-4-chloro-2-ethoxybenzoic acid methyl ester

Product 1

HCID 68683983rac-(4S*,5R*)-5-[4,5-Bis-(4-chlorophenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-N-tert-butyl-2-chloro-4-ethoxybenzenesulfonamide

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 5-tert-butylsulfamoyl-4-chloro-2-ethoxybenzoic acid methyl ester (example 43) in the presence of trimethylaluminum to give the title compound. HR-MS (ES, m/z) calculated for C29H33N3O3SCl3 [(M+H)+] 608.1303, observed 608.1300.

Sources & evidence

ORD record
ord-be39ec07b7ab4ee6b0a7be1481119278
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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