4-Bromobenzyl bromide → 3-[(4-Bromophenyl)methyl]-2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one

HRID 1994280

Reaction equation

HRID 1994280 reaction equation
Cl.[CH2:2]([C:6]1[NH:10][C:9](=[O:11])[C:8]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[N:7]=1)[CH2:3][CH2:4][CH3:5].[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1>>[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:10]2[C:9](=[O:11])[C:8]3([CH2:15][CH2:14][CH2:13][CH2:12]3)[N:7]=[C:6]2[CH2:2][CH2:3][CH2:4][CH3:5])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 685274-Bromobenzyl bromideHCID 101769952-Butyl-1,3-diazaspiro(4.4)non-1-en-4-one hydrochloride

Product 1

HCID 102481273-[(4-Bromophenyl)methyl]-2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one

Procedure

In this application further describes another process comprising the steps of reacting 2-butyl-1,3-diazaspiro[4,4]non-1-en-4-one monohydrochloride (A) with 4-bromobenzyl bromide (B) in presence of base and solvent to give 3-[4-bromobenzyl]-2-butyl-1,3-diazaspiro[4,4]non-1-en-4-one (C) which is condensed with 2-[2′-(triphenylmethyl-2′H-tetrazol-5′-yl)phenyl boronic acid in the presence of tetrakis triphenyl phosphine palladium and base to give Irbesartan (I).

Sources & evidence

ORD record
ord-5925a54fd7c14b39ae84cee5567821e7
Source dataset
uspto-grants-2010_01
Patent number
US07652147B2

Linked notes

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