4-[(Cyclohexylmethylamino)methyl]phenylamine hydrochloride → 3-(4'-Chlorobiphenyl-4-yl)propynoic acid-{4-[(cyclohexylmethylamino)methyl]phenyl}amide

HRID 735045Notes

Reaction equation

HRID 735045 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]([OH:18])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.[CH:20]1([CH2:26][NH:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>ClCCl.CO>[CH:20]1([CH2:26][NH:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:16](=[O:18])[C:15]#[C:14][C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)=[CH:13][CH:12]=3)=[CH:31][CH:30]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 688161474-[(Cyclohexylmethylamino)methyl]phenylamine hydrochlorideHCID 68816492(4'-Chlorobiphenyl-4-yl)propynoic acid

Product 1

HCID 688167433-(4'-Chlorobiphenyl-4-yl)propynoic acid-{4-[(cyclohexylmethylamino)methyl]phenyl}amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 3.8. from (4′-chlorobiphenyl-4-yl)propynoic acid and 4-[(cyclohexylmethylamino)methyl]phenylamine hydrochloride. Yield: 60 mg (13% of theory); melting point: 205° C.-210° C.; C29H29ClN2O (M=457.01); calc.: molecular ion peak (M+H)+: 457/459 (Cl); found: molecular ion peak (M+H)+: 457/459 (Cl); Rf value: 0.60 (silica gel, dichloromethane/methanol (90:10)).

Workup

  1. customPrepared analogously to Example 3.8

Sources & evidence

ORD record
ord-935ca1e300454c03bc776431e9201680
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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