N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide

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Chemical Name:N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide
CAS No.:1432511-79-9
Molecular Formula:C₁₉H₁₄F₅N₅O₂
Molecular Weight:439.344
Hs Code.:

Synonyms:N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide

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Chemical Property of N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide

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Technology Process of N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide

There total 21 articles about N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide 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: 66.0%

: 1432511-77-7
(4S,6S)-4-(5-amino-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

: 53234-55-2
5-cyano-pyridine-2-carboxylic acid

: 1432511-79-9
N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide

Guidance literature:: 5-cyano-pyridine-2-carboxylic acid; With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; at 0 ℃; for 0.5h;

(4S,6S)-4-(5-amino-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine; In methanol; at 0 - 22 ℃; for 20h;
DOI:10.1021/jm400225m

Reference yield:

: (3S,5S)-rac-3-(fluoromethyl)-3-(2-fluorophenyl)-5-(trifluoromethyl)isoxazolidine

: 1432511-79-9
N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: chiralpack AD / n-heptane; ethanol

2.1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / 20 - 25 °C / Inert atmosphere

3.1: ethanol; acetonitrile / 20 h / 85 °C / Sealed tube; Inert atmosphere

4.1: sulfuric acid; nitric acid / 0.5 h / 0 °C

5.1: palladium 10% on activated carbon; hydrogen; triethylamine / ethanol / 2 h / 22 °C

6.1: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 0.5 h / 0 °C

6.2: 20 h / 0 - 22 °C

With sulfuric acid; palladium 10% on activated carbon; hydrogen; nitric acid; ammonium formate; triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; ethanol; n-heptane; acetonitrile;
DOI:10.1021/jm400225m

Reference yield:

: 1432511-65-3
ethyl 5-(trifluoromethyl)-4,5-dihydroisoxazole-3-carboxylate

: 1432511-79-9
N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium tetrahydroborate / ethanol / 24 h / 0 °C / Inert atmosphere

2.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 15 h / -78 - 22 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -78 - -70 °C

3.2: 1 h / -78 - -70 °C

4.1: chiralpack AD / n-heptane; ethanol

5.1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / 20 - 25 °C / Inert atmosphere

6.1: ethanol; acetonitrile / 20 h / 85 °C / Sealed tube; Inert atmosphere

7.1: sulfuric acid; nitric acid / 0.5 h / 0 °C

8.1: palladium 10% on activated carbon; hydrogen; triethylamine / ethanol / 2 h / 22 °C

9.1: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 0.5 h / 0 °C

9.2: 20 h / 0 - 22 °C

With sodium tetrahydroborate; n-butyllithium; sulfuric acid; palladium 10% on activated carbon; hydrogen; nitric acid; ammonium formate; triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jm400225m