(2S,3R)-N-{3-[5-amino-3-cyclopropyl-2-fluoro-2-(trifluoromethyl)-3,6-dihydro-2H-1,4-oxazin-3-yl]phenyl}-5-cyanopyridine-2-carboxamide

Base Information

• Chemical Name: (2S,3R)-N-{3-[5-amino-3-cyclopropyl-2-fluoro-2-(trifluoromethyl)-3,6-dihydro-2H-1,4-oxazin-3-yl]phenyl}-5-cyanopyridine-2-carboxamide
• CAS No.: 1352417-08-3
• Molecular Formula: C₂₁H₁₇F₄N₅O₂
• Molecular Weight: 447.392
• Mol file: 1352417-08-3.mol

Synonyms:(2S,3R)-N-{3-[5-amino-3-cyclopropyl-2-fluoro-2-(trifluoromethyl)-3,6-dihydro-2H-1,4-oxazin-3-yl]phenyl}-5-cyanopyridine-2-carboxamide

Chemical Property of (2S,3R)-N-{3-[5-amino-3-cyclopropyl-2-fluoro-2-(trifluoromethyl)-3,6-dihydro-2H-1,4-oxazin-3-yl]phenyl}-5-cyanopyridine-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-N-{3-[5-amino-3-cyclopropyl-2-fluoro-2-(trifluoromethyl)-3,6-dihydro-2H-1,4-oxazin-3-yl]phenyl}-5-cyanopyridine-2-carboxamide

There total 12 articles about (2S,3R)-N-{3-[5-amino-3-cyclopropyl-2-fluoro-2-(trifluoromethyl)-3,6-dihydro-2H-1,4-oxazin-3-yl]phenyl}-5-cyanopyridine-2-carboxamide 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: 43.0%

C14H15F4N3O (1352420-05-3) + 5-cyano-pyridine-2-carboxylic acid (53234-55-2) → (2S,3R)-N-{3-[5-amino-3-cyclopropyl-2-fluoro-2-(trifluoromethyl)-3,6-dihydro-2H-1,4-oxazin-3-yl]phenyl}-5-cyanopyridine-2-carboxamide (1352417-08-3)

Guidance literature:

With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; at 0 ℃; for 4h;

Reference yield:

ethyl 2-(3-bromo-phenyl)-2-oxo-acetate (62123-80-2) → (2S,3R)-N-{3-[5-amino-3-cyclopropyl-2-fluoro-2-(trifluoromethyl)-3,6-dihydro-2H-1,4-oxazin-3-yl]phenyl}-5-cyanopyridine-2-carboxamide (1352417-08-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: titanium(IV) tetraethanolate / n-heptane / 24 h / 80 °C

2.1: dichloromethane / 0.67 h / -40 °C

3.1: sodium hydroxide; water / methanol / 4 h / Reflux

4.1: hydrogenchloride / 1,4-dioxane; water / 0.5 h / 20 °C

5.1: sodium hydroxide / water; tetrahydrofuran / 15 °C / pH 10 - 11

5.2: pH 2

6.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 2 h / 8 °C

7.1: tetrabutylammonium triphenyldifluorosilicate / tetrahydrofuran / 2 h / 20 °C

8.1: diethylamino-sulfur trifluoride / dichloromethane / 1 h / 20 °C

9.1: tetraphosphorus decasulfide / tetrahydrofuran / 3 h / 20 - 70 °C

10.1: ammonium hydroxide; ammonia / water; quinoline / 1 h / 140 °C / Microwave irradiation

11.1: copper(l) iodide; N,N`-dimethylethylenediamine; sodium carbonate / dimethyl sulfoxide / 6 h / 110 °C

12.1: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 4 h / 0 °C

With hydrogenchloride; titanium(IV) tetraethanolate; ammonium hydroxide; copper(l) iodide; tetraphosphorus decasulfide; diethylamino-sulfur trifluoride; ammonia; water; sodium hydrogencarbonate; sodium carbonate; tetrabutylammonium triphenyldifluorosilicate; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; sodium hydroxide; N,N`-dimethylethylenediamine; In tetrahydrofuran; 1,4-dioxane; quinoline; methanol; n-heptane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

C11H12BrNO2*ClH (1352419-97-6) → (2S,3R)-N-{3-[5-amino-3-cyclopropyl-2-fluoro-2-(trifluoromethyl)-3,6-dihydro-2H-1,4-oxazin-3-yl]phenyl}-5-cyanopyridine-2-carboxamide (1352417-08-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydroxide / water; tetrahydrofuran / 15 °C / pH 10 - 11

1.2: pH 2

2.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 2 h / 8 °C

3.1: tetrabutylammonium triphenyldifluorosilicate / tetrahydrofuran / 2 h / 20 °C

4.1: diethylamino-sulfur trifluoride / dichloromethane / 1 h / 20 °C

5.1: tetraphosphorus decasulfide / tetrahydrofuran / 3 h / 20 - 70 °C

6.1: ammonium hydroxide; ammonia / water; quinoline / 1 h / 140 °C / Microwave irradiation

7.1: copper(l) iodide; N,N`-dimethylethylenediamine; sodium carbonate / dimethyl sulfoxide / 6 h / 110 °C

8.1: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 4 h / 0 °C

With ammonium hydroxide; copper(l) iodide; tetraphosphorus decasulfide; diethylamino-sulfur trifluoride; ammonia; sodium hydrogencarbonate; sodium carbonate; tetrabutylammonium triphenyldifluorosilicate; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; sodium hydroxide; N,N`-dimethylethylenediamine; In tetrahydrofuran; quinoline; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

C₁₄H₁₅F₄N₃O

5-cyano-pyridine-2-carboxylic acid

ethyl 2-(3-bromo-phenyl)-2-oxo-acetate

C₁₅H₂₀BrNO₃S

Refernces