N'-(2-((3,4-difluorobenzyl)carbamoyl)-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)-N,N-dimethylethanediamide

Base Information

• Chemical Name: N'-(2-((3,4-difluorobenzyl)carbamoyl)-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)-N,N-dimethylethanediamide
• CAS No.: 1188425-47-9
• Molecular Formula: C₂₃H₂₅F₂N₅O₅
• Molecular Weight: 489.479
• Mol file: 1188425-47-9.mol

Synonyms:N'-(2-((3,4-difluorobenzyl)carbamoyl)-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)-N,N-dimethylethanediamide

Chemical Property of N'-(2-((3,4-difluorobenzyl)carbamoyl)-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)-N,N-dimethylethanediamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N'-(2-((3,4-difluorobenzyl)carbamoyl)-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)-N,N-dimethylethanediamide

There total 9 articles about N'-(2-((3,4-difluorobenzyl)carbamoyl)-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)-N,N-dimethylethanediamide 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: 6.0%

→ N'-(2-((3,4-difluorobenzyl)carbamoyl)-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)-N,N-dimethylethanediamide (1188425-47-9)

Guidance literature:

Reference yield:

N,N-dimethyloxamic acid (32833-96-8) + ethyl 10-(((benzyloxy)carbonyl)amino)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a] azepine-2-carboxylate (1188429-06-2) + 3,4-difluorobenzylamine (72235-53-1) → N'-(2-((3,4-difluorobenzyl)carbamoyl)-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)-N,N-dimethylethanediamide (1188425-47-9)

Guidance literature:

ethyl 10-(((benzyloxy)carbonyl)amino)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a] azepine-2-carboxylate; With palladium 10% on activated carbon; hydrogen; In methanol; for 18h;

N,N-dimethyloxamic acid; With dmap; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

3,4-difluorobenzylamine; With triethylamine; In ethanol; at 90 ℃;

DOI:10.1016/j.bmc.2020.115541

Reference yield:

C16H22ClN3O3 → N'-(2-((3,4-difluorobenzyl)carbamoyl)-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)-N,N-dimethylethanediamide (1188425-47-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: water / 24 h / 20 °C

2.1: 125 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 90 °C

4.1: palladium 10% on activated carbon; hydrogen / methanol / 18 h

4.2: 5 h / 20 °C

4.3: 90 °C

With palladium 10% on activated carbon; hydrogen; potassium carbonate; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2020.115541

upstream raw materials:

(1,4-dioxaspiro[4.5]dec-8-yl)methanol

8-(chloromethyl)-1,4-dioxaspiro[4.5]decane

benzyl 4-(chloromethyl)-1-cyanocyclohexylcarbamate

N,N-dimethyloxamic acid

Refernces

• 1、 -. "HIV Integrase Inhibitors". Page/Page column 118-119. . Retrieved 2009/10/17.