ethyl 2-((2-((4-cyanophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)acetate

Base Information

• Chemical Name: ethyl 2-((2-((4-cyanophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)acetate
• CAS No.: 1370706-18-5
• Molecular Formula: C₂₉H₂₉F₂N₃O₄
• Molecular Weight: 521.564
• Mol file: 1370706-18-5.mol

Synonyms:ethyl 2-((2-((4-cyanophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)acetate

Chemical Property of ethyl 2-((2-((4-cyanophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-((2-((4-cyanophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)acetate

There total 8 articles about ethyl 2-((2-((4-cyanophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)acetate 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: 58.0%

4-((7-((3,5-difluorobenzyl)amino)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy)benzonitrile (1370706-10-7) + ethyl bromoacetate (105-36-2) → ethyl 2-((2-((4-cyanophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)acetate (1370706-18-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 24h;

DOI:10.1016/j.ejmech.2012.01.059

Reference yield:

4-[(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile (1056737-14-4) → ethyl 2-((2-((4-cyanophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)acetate (1370706-18-5)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium on carbon; hydrogen / tetrahydrofuran / 2 h / 20 °C

2: sodium triacetoxyborohydride / 1,2-dichloro-ethane / 6 h / 20 °C

3: N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate / acetonitrile / 24 h / 60 °C

With sodium triacetoxyborohydride; palladium on carbon; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; potassium carbonate; In tetrahydrofuran; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/j.bmcl.2011.06.089

Reference yield:

(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methanol (1056737-05-3) → ethyl 2-((2-((4-cyanophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)acetate (1370706-18-5)

Guidance literature:

Multi-step reaction with 4 steps

1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48 h / Reflux

2: palladium on carbon; hydrogen / tetrahydrofuran / 2 h / 20 °C

3: sodium triacetoxyborohydride / 1,2-dichloro-ethane / 6 h / 20 °C

4: N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate / acetonitrile / 24 h / 60 °C

With sodium triacetoxyborohydride; di-isopropyl azodicarboxylate; palladium on carbon; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; potassium carbonate; triphenylphosphine; In tetrahydrofuran; 1,2-dichloro-ethane; acetonitrile; 1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2011.06.089

upstream raw materials:

(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methanol

4-[(2,4-dimethyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile

4-[(7-amino-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile

4-((7-((3,5-difluorobenzyl)amino)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy)benzonitrile

Downstream raw materials:

C₂₉H₃₂F₂N₄O₄

2-((2-((4-carbamimidoylphenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)acetic acid