Methanol → 2-[4-[2-(1-Imidazolyl)ethoxy]phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene Dioxalate

HRID 377412Notes

Reaction equation

HRID 377412 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[C:9]=2[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.Cl[CH2:33][CH2:34][N:35]1[CH:39]=[CH:38][N:37]=[CH:36]1.C1[CH2:44][O:43]CC1.[NH4+].[OH-:46].[CH3:47][OH:48]>C(Cl)(Cl)Cl>[C:25]([OH:24])(=[O:43])[C:47]([OH:48])=[O:46].[C:44]([OH:43])(=[O:1])[C:47]([OH:48])=[O:46].[N:35]1([CH2:34][CH2:33][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[S:12][C:11]4[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=4[C:9]=3[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:28][CH2:29][CH2:30][CH2:31]4)=[CH:20][CH:19]=3)=[CH:4][CH:3]=2)[CH:39]=[CH:38][N:37]=[CH:36]1

Participants

7

Reactant 5

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 27575041-(2-Chloroethyl)imidazoleHCID 224626554-[3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophen-2-yl]phenol

Product 1

HCID 867551442-[4-[2-(1-Imidazolyl)ethoxy]phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene DioxalateYield 53%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

By essentially following the procedure described in Example 3, Part D, the free base of the title compound was prepared from 2-(4-hydroxyphenyl)-3-[4-[2-(1-pyrrolidinyl)-ethoxy]benzyl]benzo[b]thiophene (Example 196; Part A) and 1-(2-chloroethyl)imidazole in 53% yield following radial chromatography (SiO2 ; 45% THF and 5% TEA in hexanes then 4% MeOH in CHCl3 sat'd with NH4OH). The product was converted to the oxalate salt by the conditions described in Example 196, Part D.

Sources & evidence

ORD record
ord-99bad345ca0e44dfab7e0be349872dfd
Source dataset
uspto-grants-2000_02
Patent number
US06025382

Reaction notes

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