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

Base Information

• Chemical Name: (S)-N-(3-(2-amino-4-methyl-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloropicolinamide
• CAS No.: 1310373-43-3
• Molecular Formula: C₁₇H₁₆ClFN₄O₂
• Molecular Weight: 362.791
• Mol file: 1310373-43-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (S)-N-(3-(2-amino-4-methyl-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloropicolinamide 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: 61.0%

5-chloropicolinic acid (86873-60-1) + (S)-4-(5-amino-2-fluorophenyl)-4-methyl-5,6-dihydro-4H-1,3-oxazin-2-amine (1301740-78-2) → (S)-N-(3-(2-amino-4-methyl-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloropicolinamide (1310373-43-3)

Guidance literature:

5-chloropicolinic acid; With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; at 0 ℃; for 0.5h;

(S)-4-(5-amino-2-fluorophenyl)-4-methyl-5,6-dihydro-4H-1,3-oxazin-2-amine; In methanol; at 0 - 23 ℃; for 20h;

DOI:10.1021/jm400225m

Reference yield:

(R)-2-methylpropane-2-sulfinic acid [1-(2-fluoro-5-nitrophenyl)-(E)-ethylidene]amide (1075230-62-4) → (S)-N-(3-(2-amino-4-methyl-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloropicolinamide (1310373-43-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: zinc; copper(l) chloride / tetrahydrofuran / 0.5 h / 50 °C / Inert atmosphere

1.2: -20 °C / Inert atmosphere

2.1: lithium borohydride / tetrahydrofuran / 4 h / 0 °C

3.1: hydrogenchloride / methanol; water; 1,4-dioxane / 16 h / 0 - 22 °C

4.1: ethanol / 80 - 95 °C / Sealed tube

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

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 - 23 °C

With hydrogenchloride; lithium borohydride; palladium 10% on activated carbon; hydrogen; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; copper(l) chloride; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; 1.2: |Reformatsky Reaction;

DOI:10.1021/jm400225m

Reference yield:

1-(2-fluoro-5-nitrophenyl)ethanone (79110-05-7) → (S)-N-(3-(2-amino-4-methyl-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloropicolinamide (1310373-43-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: titanium(IV) tetraethanolate / tetrahydrofuran / 5 h / 50 - 70 °C

2.1: zinc; copper(l) chloride / tetrahydrofuran / 0.5 h / 50 °C / Inert atmosphere

2.2: -20 °C / Inert atmosphere

3.1: lithium borohydride / tetrahydrofuran / 4 h / 0 °C

4.1: hydrogenchloride / methanol; water; 1,4-dioxane / 16 h / 0 - 22 °C

5.1: ethanol / 80 - 95 °C / Sealed tube

6.1: palladium 10% on activated carbon; hydrogen / ethanol

7.1: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 0.5 h / 0 °C

7.2: 20 h / 0 - 23 °C

With hydrogenchloride; titanium(IV) tetraethanolate; lithium borohydride; palladium 10% on activated carbon; hydrogen; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; copper(l) chloride; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; 2.2: |Reformatsky Reaction;

DOI:10.1021/jm400225m

upstream raw materials:

(S)-ethyl 3-((R)-1,1-dimethylethylsulfinamido)-3-(2-fluoro-5-nitrophenyl)butanoate

(S)-3-amino-3-(2-fluoro-5-nitrophenyl)butan-1-ol

(R)-2-methyl-propane-2-sulfinic acid [(S)-1-(2-fluoro-5-nitro-phenyl)-3-hydroxy-1-methyl-propyl]-amide

(S)-4-(2-fluoro-5-nitrophenyl)-4-methyl-5,6-dihydro-4H-1,3-oxazin-2-amine