(+/-)-4-(2-amino-5-(5-((dimethylamino)methyl)-3-methylthiophen-2-yl)pyridin-3-yl)-2-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzamide

Base Information

Chemical Name:(+/-)-4-(2-amino-5-(5-((dimethylamino)methyl)-3-methylthiophen-2-yl)pyridin-3-yl)-2-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzamide
CAS No.:1364268-70-1
Molecular Formula:C₂₉H₂₉F₃N₄O₂S
Molecular Weight:554.636
Hs Code.:

Synonyms:(+/-)-4-(2-amino-5-(5-((dimethylamino)methyl)-3-methylthiophen-2-yl)pyridin-3-yl)-2-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzamide

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Chemical Property of (+/-)-4-(2-amino-5-(5-((dimethylamino)methyl)-3-methylthiophen-2-yl)pyridin-3-yl)-2-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzamide

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Technology Process of (+/-)-4-(2-amino-5-(5-((dimethylamino)methyl)-3-methylthiophen-2-yl)pyridin-3-yl)-2-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzamide

There total 8 articles about (+/-)-4-(2-amino-5-(5-((dimethylamino)methyl)-3-methylthiophen-2-yl)pyridin-3-yl)-2-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

: 1364267-75-3
(+/-)-methyl 4-(2-amino-5-(5-((dimethylamino)methyl)-3-methylthiophen-2-yl)pyridin-3-yl)-2-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzoate

: 1364268-70-1
(+/-)-4-(2-amino-5-(5-((dimethylamino)methyl)-3-methylthiophen-2-yl)pyridin-3-yl)-2-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzamide

Guidance literature:: With ammonia; In methanol; at 80 ℃; for 96h;
DOI:10.1021/jm201683b

Reference yield:

: 1666-28-0
4-bromosalicylic acid

: 1364268-70-1
(+/-)-4-(2-amino-5-(5-((dimethylamino)methyl)-3-methylthiophen-2-yl)pyridin-3-yl)-2-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzamide

Guidance literature:: Multi-step reaction with 6 steps

1: sulfuric acid / 24 h / 80 °C

2: di-tert-butyl-diazodicarboxylate; triphenylphosphine / dichloromethane / 0 - 20 °C

3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / N,N-dimethyl-formamide / 1.5 h / 100 °C / Microwave irradiation

4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydrogencarbonate / water; N,N-dimethyl-formamide / 1.5 h / 100 °C / Microwave irradiation

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; N,N-dimethyl-formamide / 1 h / 110 °C / Microwave irradiation

6: ammonia / methanol / 96 h / 80 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; di-tert-butyl-diazodicarboxylate; sulfuric acid; ammonia; potassium acetate; sodium hydrogencarbonate; sodium carbonate; triphenylphosphine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 2: Mitsunobu reaction;
DOI:10.1021/jm201683b

Reference yield:

: 14282-76-9
2-bromo-3-methylthiophene

: 1364268-70-1
(+/-)-4-(2-amino-5-(5-((dimethylamino)methyl)-3-methylthiophen-2-yl)pyridin-3-yl)-2-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.67 h / -78 °C

1.2: -78 - 20 °C

2.1: triethylamine / 1,2-dichloro-ethane / 0.17 h

3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / N,N-dimethyl-formamide / 1.5 h / 100 °C / Microwave irradiation

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; N,N-dimethyl-formamide / 1 h / 110 °C / Microwave irradiation

5.1: ammonia / methanol / 96 h / 80 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ammonia; potassium acetate; sodium carbonate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; n-heptane; ethylbenzene; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/jm201683b