3-Chloro-4-(2-diethylaminoethyl)phenylamine → 3-(3-bromobiphenyl-4-yl)propynoic acid-[3-chloro-4-(2-diethylaminoethyl)phenyl]amide Hydrochloride

HRID 735160Notes

Reaction equation

HRID 735160 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[C:9][C:10]([OH:12])=O.[Cl:19][C:20]1[CH:21]=[C:22]([NH2:33])[CH:23]=[CH:24][C:25]=1[CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30]>ClCCl.CO>[ClH:19].[Cl:19][C:20]1[CH:21]=[C:22]([NH:33][C:10](=[O:12])[C:9]#[C:8][C:7]2[CH:6]=[CH:5][C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:3][C:2]=2[Br:1])[CH:23]=[CH:24][C:25]=1[CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 596916173-Chloro-4-(2-diethylaminoethyl)phenylamineHCID 68818231(3-bromobiphenyl-4-yl)propynoic Acid

Product 1

HCID 688165033-(3-bromobiphenyl-4-yl)propynoic acid-[3-chloro-4-(2-diethylaminoethyl)phenyl]amide Hydrochloride

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 2.3.f. from (3-bromobiphenyl-4-yl)propynoic acid and 3-chloro-4-(2-diethylaminoethyl)phenylamine. Yield: 95 mg (23.8% of theory); C27H26BrClN2O*HCl (M=546.32); calc.: molecular ion peak (M+H)+: 509/11/13; found: molecular ion peak (M+H)+: 509/11/13; Rf value: 0.3 (silica gel, dichloromethane/methanol (90:10)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-36ab13ac32b349d48362282541917b35
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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