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

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)-2-oxoacetate
• CAS No.: 1384181-34-3
• Molecular Formula: C₂₉H₂₇F₂N₃O₅
• Molecular Weight: 535.547
• Mol file: 1384181-34-3.mol

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

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)-2-oxoacetate

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)-2-oxoacetate

There total 6 articles about ethyl 2-((2-((4-cyanophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)-2-oxoacetate 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: 55.0%

4-((7-((3,5-difluorobenzyl)amino)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy)benzonitrile (1370706-10-7) + Ethyl oxalyl chloride (4755-77-5) → ethyl 2-((2-((4-cyanophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)-2-oxoacetate (1384181-34-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.ejmech.2012.01.059

Reference yield:

3,4-dihydro-2-methyl-7-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid ethyl ester (154365-36-3) → ethyl 2-((2-((4-cyanophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)-2-oxoacetate (1384181-34-3)

Guidance literature:

Multi-step reaction with 7 steps

1: potassium fluoride / N,N-dimethyl-formamide / 20 °C

2: dimethylsulfide borane complex / tetrahydrofuran / 4 h / Reflux

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

4: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 2 h / 20 °C

5: methanol / 5 h / 20 °C / Inert atmosphere; Molecular sieve

6: sodium tetrahydroborate / methanol / 2 h / 20 °C

7: triethylamine / dichloromethane / 2 h / 20 °C

With potassium fluoride; sodium tetrahydroborate; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; palladium 10% on activated carbon; hydrogen; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3: Mitsunobu reaction;

DOI:10.1016/j.ejmech.2012.01.059

Reference yield:

ethyl 2,4-dimethyl-7-nitro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate (847671-40-3) → ethyl 2-((2-((4-cyanophenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(3,5-difluorobenzyl)amino)-2-oxoacetate (1384181-34-3)

Guidance literature:

Multi-step reaction with 6 steps

1: dimethylsulfide borane complex / tetrahydrofuran / 4 h / Reflux

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

3: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 2 h / 20 °C

4: methanol / 5 h / 20 °C / Inert atmosphere; Molecular sieve

5: sodium tetrahydroborate / methanol / 2 h / 20 °C

6: triethylamine / dichloromethane / 2 h / 20 °C

With sodium tetrahydroborate; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; palladium 10% on activated carbon; hydrogen; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 2: Mitsunobu reaction;

DOI:10.1016/j.ejmech.2012.01.059

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

Ethyl oxalyl chloride

Downstream raw materials:

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