4-(2-Diethylaminopropoxy)phenylamine → 3-(2-Chloro-4-trifluoromethylphenyl)propynoic acid-[4-(2-diethylaminopropoxy)phenyl]amide

HRID 735066Notes

Reaction equation

HRID 735066 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[CH:4]([CH3:14])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)[CH3:2].[Cl:17][C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=1[C:28]#[C:29][C:30](O)=[O:31]>ClCCl.CO>[CH2:15]([N:3]([CH2:1][CH3:2])[CH:4]([CH3:14])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:30](=[O:31])[C:29]#[C:28][C:19]2[CH:20]=[CH:21][C:22]([C:24]([F:26])([F:25])[F:27])=[CH:23][C:18]=2[Cl:17])=[CH:11][CH:12]=1)[CH3:16]

Participants

4

Reactant 2

HCID 688160894-(2-Diethylaminopropoxy)phenylamineHCID 68817422(2-Chloro-4-trifluoromethylphenyl)propynoic acid

Product 1

HCID 688182283-(2-Chloro-4-trifluoromethylphenyl)propynoic acid-[4-(2-diethylaminopropoxy)phenyl]amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 2.3.f. from 67 mg (0.3 mmol) of 4-(2-diethylaminopropoxy)phenylamine and 75 mg (0.3 mmol) of (2-chloro-4-trifluoromethylphenyl)propynoic acid. Yield: 71 mg (52% of theory); melting point: 172° C.-176° C.; C23H24ClF3N2O2 (M=452.90); calc.: molecular ion peak (M+H)+: 453/455; found: molecular ion peak (M+H)+: 453/455; Rf value: 0.30 (silica gel, dichloromethane/methanol (9:1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-60ef306895e54402bc67ecd439c3bf58
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

Loading…