Toluene → 2-Butyl-4-chloro-1-[[2'-[2-(triphenylmethyl)-2H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-Imidazole-5-carboxaldehyde

HRID 654333Notes

Reaction equation

HRID 654333 reaction equation
C1(C)C=CC=CC=1.CN(C)C(=O)C.[CH2:14]([C:18]1[N:19]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:39]3[N:40]=[N:41][N:42]([C:44]([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[N:43]=3)=[CH:29][CH:28]=2)[C:20]([CH2:24][OH:25])=[C:21]([Cl:23])[N:22]=1)[CH2:15][CH2:16][CH3:17].C(OCC)(=O)C>C(O)C>[CH2:14]([C:18]1[N:19]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:39]3[N:40]=[N:41][N:42]([C:44]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)[N:43]=3)=[CH:31][CH:32]=2)[C:20]([CH:24]=[O:25])=[C:21]([Cl:23])[N:22]=1)[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 31374DimethylacetamideHCID 10865273Trityllosartan

Product 1

HCID 156980542-Butyl-4-chloro-1-[[2'-[2-(triphenylmethyl)-2H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-Imidazole-5-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(4'-bromomethyl-1,1'-biphenyl-2-yl)-2triphenylmethyl-2H-tetrazole (0.102 m=63.1 g), 2-n-butyl-4-chloro-1H-imidazole-5-carboxaldehyde (0.113 m=21.1 g) and anhydrous potassium carbonate (0.135 m=18.6 g) in 251 g of N,N-dimethylacetamide was stirred at 0°-5° C. for 8 hours and the temperature of the reaction was raised to 25° C. for an additional 4 hours. Normally the product of this step was not isolated but reduced with sodium borohydride to give 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol. The title compound can be isolated by extraction into toluene from aqueous N,N-dimethylacetamide, concentration of the toluene solution, and crystallization from ethyl acetate or ethanol, mp 145°-147° C. (dec.).

Sources & evidence

ORD record
ord-8bf4acc87f3e4fd69d9826c12b24572a
Source dataset
uspto-grants-1992_07
Patent number
US05130439

Reaction notes

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