Potassium Carbonate → Rac.-n-{1-[6-chloro-1-(methoxycarbonylmethyl)-1h-benzimidazol-2-yl]-2-(4-methoxy-carbonylmethoxyphenyl)ethyl}-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide

HRID 2053918Notes

Reaction equation

HRID 2053918 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]([NH:19][C:20](=[O:35])[C:21]3[CH:26]=[CH:25][C:24]([C:27]([N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)=[O:28])=[C:23]([CH3:34])[CH:22]=3)[CH2:11][C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[NH:7][C:6]=2[CH:36]=1.Br[CH2:38][C:39]([O:41][CH3:42])=[O:40].[C:43](=[O:46])([O-])[O-].[K+].[K+].ClCl.Cl[CH2:52]Cl.[CH2:54]([OH:56])C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]([NH:19][C:20](=[O:35])[C:21]3[CH:26]=[CH:25][C:24]([C:27]([N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)=[O:28])=[C:23]([CH3:34])[CH:22]=3)[CH2:11][C:12]3[CH:13]=[CH:14][C:15]([O:18][CH3:52])=[CH:16][C:17]=3[O:56][CH:54]=[C:43]=[O:46])[N:7]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[C:6]=2[CH:36]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 24526ChlorineHCID 60984Methyl bromoacetateHCID 21584144Dichloromethane ethanolHCID 59737129N-[1-(6-chloro-1H-benzimidazol-2-yl)-2-(4-hydroxyphenyl)ethyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide

Product 1

HCID 86760609Rac.-n-{1-[6-chloro-1-(methoxycarbonylmethyl)-1h-benzimidazol-2-yl]-2-(4-methoxy-carbonylmethoxyphenyl)ethyl}-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamideYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 6b from N-[1-(6-chloro-1H-benzimidazol-2-yl)-2-(4-hydroxyphenyl)ethyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide, methyl bromoacetate, and potassium carbonate in dimethylformamide. Yield: 17%; Rf value: 0.65 (silica gel; dichloromethane/ethanol=19:1); C34H35ClN4O7 (647.13); mass spectrum: (M+H)+=647/649 (chlorine isotope).

Sources & evidence

ORD record
ord-18051ca0d1004eaeb280f3ad13f9045f
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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