N-{3-[2-(2-acetyl-1H-pyrrolo[2,3-b]pyridin-5-yl)ethyl]-4-methylphenyl}-4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)benzamide

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Chemical Name:N-{3-[2-(2-acetyl-1H-pyrrolo[2,3-b]pyridin-5-yl)ethyl]-4-methylphenyl}-4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)benzamide
CAS No.:1616689-37-2
Molecular Formula:C₃₃H₃₆F₃N₅O₂
Molecular Weight:591.676
Hs Code.:

N-{3-[2-(2-acetyl-1H-pyrrolo[2,3-b]pyridin-5-yl)ethyl]-4-methylphenyl}-4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)benzamide

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Chemical Property of N-{3-[2-(2-acetyl-1H-pyrrolo[2,3-b]pyridin-5-yl)ethyl]-4-methylphenyl}-4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)benzamide

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Technology Process of N-{3-[2-(2-acetyl-1H-pyrrolo[2,3-b]pyridin-5-yl)ethyl]-4-methylphenyl}-4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)benzamide

There total 5 articles about N-{3-[2-(2-acetyl-1H-pyrrolo[2,3-b]pyridin-5-yl)ethyl]-4-methylphenyl}-4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)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: 15.0%

: 1616689-37-2
N-{3-[2-(2-acetyl-1H-pyrrolo[2,3-b]pyridin-5-yl)ethyl]-4-methylphenyl}-4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)benzamide

Guidance literature:: With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

Reference yield:

: 1616689-94-1
2-acetyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

: 1616689-37-2
N-{3-[2-(2-acetyl-1H-pyrrolo[2,3-b]pyridin-5-yl)ethyl]-4-methylphenyl}-4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)benzamide

Guidance literature:: Multi-step reaction with 5 steps

1: diisobutylaluminium hydride / toluene; cyclohexane / 1.5 h / 0 °C

2: manganese(IV) oxide / tetrahydrofuran / 20 °C

3: lithium hydroxide / methanol / 20 °C

4: palladium 10% on activated carbon; hydrogen / N,N-dimethyl-formamide / 20 °C / 7500.75 Torr

5: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C / Schlenk technique; Inert atmosphere

With manganese(IV) oxide; palladium 10% on activated carbon; hydrogen; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; In tetrahydrofuran; methanol; cyclohexane; N,N-dimethyl-formamide; toluene; 3: |Wittig Olefination;
DOI:10.1021/acs.jmedchem.6b00087

Reference yield:

: 1616689-78-1
2-(1-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

: 1616689-37-2
N-{3-[2-(2-acetyl-1H-pyrrolo[2,3-b]pyridin-5-yl)ethyl]-4-methylphenyl}-4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)benzamide

Guidance literature:: Multi-step reaction with 4 steps

1: manganese(IV) oxide / tetrahydrofuran / 20 °C

2: lithium hydroxide / methanol / 20 °C

3: palladium 10% on activated carbon; hydrogen / N,N-dimethyl-formamide / 20 °C / 7500.75 Torr

4: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C / Schlenk technique; Inert atmosphere

With manganese(IV) oxide; palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 2: |Wittig Olefination;
DOI:10.1021/acs.jmedchem.6b00087