Methanol → HCID 69691131, compound

HRID 1937166Notes

Reaction equation

HRID 1937166 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.Cl.[N:19]1([CH2:24][CH2:25][O:26][C:27]2[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1.[CH3:36][OH:37]>C(Cl)Cl>[C:31]([OH:33])(=[O:32])[C:36]([OH:2])=[O:37].[N:19]1([CH2:24][CH2:25][O:26][C:27]2[CH:35]=[CH:34][C:30]([CH2:31][C:10]3[C:11]4[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=4[S:13][C:9]=3[C:6]3[CH:7]=[CH:8][C:3]([O:2][CH2:1][C@@H:20]4[CH2:21][CH2:22][C:36](=[O:37])[NH:19]4)=[CH:4][CH:5]=3)=[CH:29][CH:28]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 887MethanolHCID 41373912-(4-Methoxyphenyl)benzothiopheneHCID 131748684-(2-Pyrrolidin-1-ylethoxy)benzoic acid hydrochloride

Product 1

HCID 69691131HCID 69691131, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By essentially following the procedure detailed in Example 1, Part D, but using thionyl chloride in refluxing dichloromethane to form the benzoyl choride, the title compound was prepared from 2-(4-methoxyphenyl)-benzo[b]thiophene and 4-[2-(1-pyrrolidinyl)ethoxy]benzoic acid hydrochloride in 59% yield as an oil following radial chromatography (SiO2; gradient of 2-5% MeOH in CH2Cl2).

Sources & evidence

ORD record
ord-b6a3dc2cc5244d6bb90be8ce106252ef
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

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