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

HRID 735141Notes

Reaction equation

HRID 735141 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]([NH2:36])[CH:22]=[CH:23][C:24]=1[O:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([O:34][CH3:35])[CH2:30][CH2:29]1>ClCCl.CO>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([NH:36][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]([O:34][CH3:35])[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 688158643-Methoxy-4-[2-(4-methoxypiperidin-1-yl)ethoxy]phenylamineHCID 68817422(2-Chloro-4-trifluoromethylphenyl)propynoic acid

Product 1

HCID 578457263-(2-Chloro-4-trifluoromethylphenyl)propynoic acid-{3-methoxy-4-[2-(4-methoxypiperidin-1-yl)ethoxy]phenyl}amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 2.3.f. from 150 mg (0.6 mmol) of (2-chloro-4-trifluoromethylphenyl)propynoic acid and 186 mg (0.66 mmol) of 3-methoxy-4-[2-(4-methoxypiperidin-1-yl)ethoxy]phenylamine. Yield: 20 mg (7% of theory); melting point: 195° C.-197° C.; C25H26ClF3N2O4 (M=510.93); calc.: molecular ion peak (M+H)+: 511/513 (Cl); found: molecular ion peak (M+H)+: (M+H)+: 511/513 (Cl); Rf value: 0.3 (silica gel, dichloromethane/methanol (9:1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-a76c52f339bf45a28cd27c9ffdf2fa3c
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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