4-(2-Diethylaminoethoxy)-3-methoxyphenylamine → 3-(2-chloro-4-trifluoromethylphenyl)propynoic acid-[3-methoxy-4-(2-diethylaminoethoxy)phenyl]amide Hydrochloride

HRID 735109Notes

Reaction equation

HRID 735109 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]#[C:13][C:14]([OH:16])=O.[CH3:17][O:18][C:19]1[CH:32]=[C:31]([NH2:33])[CH:30]=[CH:29][C:20]=1[O:21][CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26]>ClCCl.CO>[ClH:1].[CH3:17][O:18][C:19]1[CH:32]=[C:31]([NH:33][C:14](=[O:16])[C:13]#[C:12][C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=2[Cl:1])[CH:30]=[CH:29][C:20]=1[O:21][CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 224961344-(2-Diethylaminoethoxy)-3-methoxyphenylamineHCID 68817422(2-Chloro-4-trifluoromethylphenyl)propynoic acid

Product 1

HCID 688178373-(2-chloro-4-trifluoromethylphenyl)propynoic acid-[3-methoxy-4-(2-diethylaminoethoxy)phenyl]amide Hydrochloride

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 2.3.f. from 75 mg (0.30 mmol) of (2-chloro-4-trifluoromethylphenyl)propynoic acid and 79 mg (0.33 mmol) of [2-(2-methoxy-4-aminophenoxy)ethyl]diethylamine. Yield: 14 mg (10% of theory); C23H24ClF3N2O3 (M=468.90); calc.: molecular ion peak (M+H)+: 469/471; found: molecular ion peak (M+H)+: 469/471; Rf value: 0.35 (silica gel, dichloromethane/methanol (9:1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-90e4c224970f4a1d827b0df135e5a284
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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