4-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethoxy]-3-methoxyphenylamine → 3-(2-chloro-4-trifluoromethylphenyl)propynoic acid-{4-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethoxy]-3-methoxyphenyl}amide formate

HRID 735144Notes

Reaction equation

HRID 735144 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:15].[CH2:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][N:18]1[CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][C:31]=1[O:37][CH3:38]>ClCCl.CO>[CH:14]([OH:16])=[O:15].[CH2:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][N:18]1[CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([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:32][C:31]=1[O:37][CH3:38]

Participants

4

Reactant 2

HCID 688174124-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethoxy]-3-methoxyphenylamineHCID 68817422(2-Chloro-4-trifluoromethylphenyl)propynoic acid

Product 1

HCID 688184593-(2-chloro-4-trifluoromethylphenyl)propynoic acid-{4-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethoxy]-3-methoxyphenyl}amide formate

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 304 mg (0.66 mmol) of 4-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethoxy]-3-methoxyphenylamine (65%). Yield: 17 mg (5% of theory); melting point: 92° C.-95° C.; C28H24ClF3N2O3 (M=528.96)*CH2O2; calc.: molecular ion peak (M+H)+: 529/531 (Cl); found: molecular ion peak (M+H)+: 529/531 (Cl); Rf value: 0.55 (silica gel, dichloromethane/methanol (9:1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-83c8d310ca6c4741a1b212833535c135
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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