Sodium Hydroxide → Rac.-n-{1-[6-chloro-1-(hydroxycarbonylmethyl)-1h-benzimidazol-2-yl]-2-(4-hydroxyphenyl)ethyl}-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide

HRID 2053919Notes

Reaction equation

HRID 2053919 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)[N:7]([CH2:36][C:37]([O:39]C)=[O:38])[C:6]=2[CH:41]=1.[OH-].[Na+].ClCCl.C(O)C.N.ClCl>CO>[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)[N:7]([CH2:36][C:37]([OH:39])=[O:38])[C:6]=2[CH:41]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24526ChlorineHCID 22609213HCID 22609213, compoundHCID 59655244Rac.-n-{1-[6-chloro-1-(methoxycarbonylmethyl)-1h-benzimidazol-2-yl]-2-(4-hydroxyphenyl)ethyl}-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide

Product 1

HCID 59655253Rac.-n-{1-[6-chloro-1-(hydroxycarbonylmethyl)-1h-benzimidazol-2-yl]-2-(4-hydroxyphenyl)ethyl}-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamideYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared analogously to Example 19b from rac.-N-{1-[6-chloro-1-(methoxycarbonylmethyl)-1H-benzimidazol-2-yl]-2-(4-hydroxyphenyl)ethyl}-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide and sodium hydroxide solution in methanol. Yield: 79%; Rf value: 0.18 (silica gel; dichloromethane/ethanol/ammonia=9:1:0.1); C30H29ClN4O5 (561.04); mass spectrum: (M+H)+=561/563 (chlorine isotope).

Sources & evidence

ORD record
ord-38488ebb9f1e4dda9516bf74190264e9
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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