(2-Chloro-4-trifluoromethylphenyl)propynoic acid → 3-(2-Chloro-4-trifluoromethylphenyl)propynoic acid-{3-methoxy-4-[2-(4-methylpiperidin-1-yl)ethoxy]phenyl}amide

HRID 735130Notes

Reaction equation

HRID 735130 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:20]=[C:21]([NH2:35])[CH:22]=[CH:23][C:24]=1[O:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([CH3:34])[CH2:30][CH2:29]1>ClCCl.CO>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([NH:35][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:22]=[CH:23][C:24]=1[O:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([CH3:34])[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 68817422(2-Chloro-4-trifluoromethylphenyl)propynoic acidHCID 688191123-Methoxy-4-[2-(4-methylpiperidin-1-yl)ethoxy]phenylamine

Product 1

HCID 578456833-(2-Chloro-4-trifluoromethylphenyl)propynoic acid-{3-methoxy-4-[2-(4-methylpiperidin-1-yl)ethoxy]phenyl}amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 2.3.f. from (2-chloro-4-trifluoromethylphenyl)propynoic acid and 3-methoxy-4-[2-(4-methylpiperidin-1-yl)ethoxy]phenylamine. Yield: 70 mg (23.5% of theory); melting point: 207° C.-209° C.; C25H26ClF3N2O3 (M=494.94); calc.: molecular ion peak (M+H)+: 495/497; found: molecular ion peak (M+H)+: 495/497; Rf value: 0.45 (silica gel, dichloromethane/methanol (9:1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-51d1377933aa4e09ab36bdcd82c687e5
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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