N-t-Butyl-4'-bromomethylbiphenyl-2-carboxamide → Ethyl 1-{4-[2-(t-butylaminocarbonyl)phenyl]phenyl}methyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

HRID 265104Notes

Reaction equation

HRID 265104 reaction equation
[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:15][CH2:16][CH3:17])[NH:8][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH3:4])[CH3:3].[C:18]([NH:22][C:23]([C:25]1[C:26]([C:31]2[CH:36]=[CH:35][C:34]([CH2:37]Br)=[CH:33][CH:32]=2)=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19].CC(C)([O-])C.[K+]>>[C:18]([NH:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][C:34]([CH2:37][N:8]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:5]([C:2]([OH:1])([CH3:4])[CH3:3])[N:6]=[C:7]2[CH2:15][CH2:16][CH3:17])=[CH:33][CH:32]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 19036294N-t-Butyl-4'-bromomethylbiphenyl-2-carboxamideHCID 23665647Potassium tert-butoxideHCID 178440079HCID 178440079, compound

Product 1

HCID 19036152Ethyl 1-{4-[2-(t-butylaminocarbonyl)phenyl]phenyl}methyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylateYield 67.1%

Procedure

Following a procedure similar to that described in Example 68(a), but using 4.16 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (prepared as described in Preparation 9), 6.00 g of N-t-butyl-4'-bromomethylbiphenyl-2-carboxamide (prepared as described in Preparation 38) and 2.14 g of potassium t-butoxide, 5.87 g of the title compound was obtained as crystals, melting at 145°-146° C.

Sources & evidence

ORD record
ord-0ddeccb7908844f2b49bd7054e5f23a0
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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