3-Chloro-4-[2-(4-methylpiperidin-1-yl)ethyl]phenylamine → 3-(3-Bromobiphenyl-4-yl)propynoic acid-{3-chloro-4-[2-(4-methylpiperidin-1-yl)ethyl]phenyl}amide

HRID 735159Notes

Reaction equation

HRID 735159 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]([NH2:35])[CH:23]=[CH:24][C:25]=1[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([CH3:34])[CH2:30][CH2:29]1>ClCCl.CO>[Cl:19][C:20]1[CH:21]=[C:22]([NH:35][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]1[CH2:29][CH2:30][CH:31]([CH3:34])[CH2:32][CH2:33]1

Participants

4

Reactant 2

HCID 596916703-Chloro-4-[2-(4-methylpiperidin-1-yl)ethyl]phenylamineHCID 68818231(3-bromobiphenyl-4-yl)propynoic Acid

Product 1

HCID 578458193-(3-Bromobiphenyl-4-yl)propynoic acid-{3-chloro-4-[2-(4-methylpiperidin-1-yl)ethyl]phenyl}amide

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-(4-methylpiperidin-1-yl)ethyl]phenylamine. Yield: 0.24 g (50% of theory); C29H28BrClN2O (M=535.90); calc.: molecular ion peak (M+H)+: 535/37/39; found: molecular ion peak (M+H)+: 535/37/39; Rf value: 0.48 (silica gel, dichloromethane/methanol (90:10)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-b4bc4131b0bc4054b9f426436e5a9d06
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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