N-(3,5-bis-(trifluoromethyl)benzyl)-N-((2R,4r,6S)-2,6-diethylpiperidin-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine

Base Information

• Chemical Name: N-(3,5-bis-(trifluoromethyl)benzyl)-N-((2R,4r,6S)-2,6-diethylpiperidin-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine
• CAS No.: 1148129-95-6
• Molecular Formula: C₂₆H₃₀F₆N₆
• Molecular Weight: 540.555
• Mol file: 1148129-95-6.mol

Synonyms:N-(3,5-bis-(trifluoromethyl)benzyl)-N-((2R,4r,6S)-2,6-diethylpiperidin-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine

Chemical Property of N-(3,5-bis-(trifluoromethyl)benzyl)-N-((2R,4r,6S)-2,6-diethylpiperidin-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(3,5-bis-(trifluoromethyl)benzyl)-N-((2R,4r,6S)-2,6-diethylpiperidin-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine

There total 5 articles about N-(3,5-bis-(trifluoromethyl)benzyl)-N-((2R,4r,6S)-2,6-diethylpiperidin-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine 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:

tert-butyl (2R,6S)-2,6-diethyl-4-oxopiperidine-1-carboxylate (1003843-30-8) → N-(3,5-bis-(trifluoromethyl)benzyl)-N-((2R,4r,6S)-2,6-diethylpiperidin-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine (1148129-95-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: titanium(IV)isopropoxide / methanol / 20 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 55 °C

3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3.5 h / 120 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

4.2: 1 h / 20 °C / Inert atmosphere

5.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 20 h / 90 °C / Inert atmosphere

6.1: hydrogenchloride / ethyl acetate / 2 h / 20 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; hydrogen; titanium(IV)isopropoxide; sodium hydride; sodium carbonate; N-ethyl-N,N-diisopropylamine; In methanol; 1,2-dimethoxyethane; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.jmedchem.7b00900

Reference yield:

tert-butyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate (1148129-86-5) → N-(3,5-bis-(trifluoromethyl)benzyl)-N-((2R,4r,6S)-2,6-diethylpiperidin-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine (1148129-95-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 20 h / 90 °C / Inert atmosphere

2: hydrogenchloride / ethyl acetate / 2 h / 20 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; water; ethyl acetate;

DOI:10.1021/acs.jmedchem.7b00900

Reference yield:

tert-butyl (2R,4r,6S)-4-(benzylamino)-2,6-diethylpiperidine-1-carboxylate (1148130-18-0) → N-(3,5-bis-(trifluoromethyl)benzyl)-N-((2R,4r,6S)-2,6-diethylpiperidin-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine (1148129-95-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 55 °C

2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3.5 h / 120 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

3.2: 1 h / 20 °C / Inert atmosphere

4.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 20 h / 90 °C / Inert atmosphere

5.1: hydrogenchloride / ethyl acetate / 2 h / 20 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; hydrogen; sodium hydride; sodium carbonate; N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.jmedchem.7b00900

upstream raw materials:

tert-butyl (2R,4r,6S)-4-amino-2,6-diethylpiperidine-1-carboxylate

tert-butyl (2R,6S)-2,6-diethyl-4-oxopiperidine-1-carboxylate

tert-butyl (2R,4r,6S)-4-((5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate

tert-butyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate

Downstream raw materials:

cis-4-{(3,5-bis(trifluoromethyl)benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2,6-diethylpiperidine-1-carboxylic acid 3-methoxycarbonyl-propyl ester

cis-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2,6-diethyl-piperidine-1-carboxylic acid 1-tert-butoxycarbonyl-azetidin-3-yl ester

(1r,4r)-4-(((2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carbonyl)oxy)cyclohexane-1-carboxylic acid

(1r,4r)-4-(methoxycarbonyl)-cyclohexyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate