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

Base Information

• Chemical Name: N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide
• CAS No.: 1432511-80-2
• Molecular Formula: C₁₉H₁₅F₄N₅O₂
• Molecular Weight: 421.354
• Mol file: 1432511-80-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about N-(3-((4S,6S)-2-amino-4-methyl-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:

(4S,6S)-4-(5-amino-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (1432511-78-8) + 5-cyano-pyridine-2-carboxylic acid (53234-55-2) → N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide (1432511-80-2)

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-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine; In methanol; at 0 - 22 ℃; for 20h;

DOI:10.1021/jm400225m

Reference yield:

5-cyano-pyridine-2-carboxylic acid (53234-55-2) → N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide (1432511-80-2)

Guidance literature:

Reference yield:

(3S,5S)-rac-3-(2-fluorophenyl)-3-methyl-5-trifluoromethylisoxazolidine → N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyanopicolinamide (1432511-80-2)

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 / 22 - 25 °C / Inert atmosphere

3.1: ethanol; acetonitrile / 15 h / 85 °C / Sealed tube

4.1: sulfuric acid; nitric acid / 0.5 h / 0 - 22 °C

5.1: palladium 10% on activated carbon; hydrogen; triethylamine / ethanol / 3 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

upstream raw materials:

(4S,6S)-4-(5-amino-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

5-cyano-pyridine-2-carboxylic acid

3-methyl-5-(trifluoromethyl)-4,5-dihydroisoxazole

(+)-(3S,5S)-3-(2-fluorophenyl)-3-methyl-5-trifluoromethylisoxazolidine

Refernces

• 1、 Hilpert, Hans,Guba, Wolfgang,Woltering, Thomas J.,Wostl, Wolfgang,Pinard, Emmanuel,Mauser, Harald,Mayweg, Alexander V.,Rogers-Evans, Mark,Humm, Roland,Krummenacher, Daniela,Muser, Thorsten,Schnider, Christian,Jacobsen, Helmut,Ozmen, Laurence,Bergadano, Alessandra,Banner, David W.,Hochstrasser, Remo,Kuglstatter, Andreas,David-Pierson, Pascale,Fischer, Holger,Polara, Alessandra,Narquizian, Robert. "β-secretase (BACE1) inhibitors with high in vivo efficacy suitable for clinical evaluation in Alzheimer's disease". . p. 3980 - 3995. Retrieved 2013/06/27.