7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

Base Information

• Chemical Name: 7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
• CAS No.: 210236-57-0
• Molecular Formula: C₂₂H₁₉F₃N₄O₃
• Molecular Weight: 444.413
• Mol file: 210236-57-0.mol

Synonyms:7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

Chemical Property of 7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

There total 8 articles about 7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 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: 77.0%

7-((1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (210165-72-3) → 7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (210236-57-0)

Guidance literature:

With hydrogenchloride; water; hydrogen; palladium on activated charcoal; In ethanol; at 23 ℃; for 20h;

DOI:10.1055/s-1998-2055

Reference yield:

Dibenzyl-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-amine (164799-10-4) → 7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (210236-57-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 87 percent / NCS / CH₂Cl₂ / 3 h / -78 - -30 °C

2: 95 percent / MeONa / 20 h / 20 °C

3: 89 percent / DIBAH / tetrahydrofuran / 1.) 60 deg C, 5 h, 2.) 20 deg C, 3 d

4: 50 percent / CHCl₃ / 1.) 50 deg C, 1.75 h, 2.) 20 deg C, 2 h

5: 74 percent / H₂O, HCl / CHCl₃ / 14 h / Ambient temperature

6: 80 percent / NEt₃ / acetonitrile / 5 h / 60 °C

7: 77 percent / H₂O, HCl, H₂ / 5percent Pd/C / ethanol / 20 h / 23 °C

With hydrogenchloride; N-chloro-succinimide; water; hydrogen; sodium methylate; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; acetonitrile;

DOI:10.1055/s-1998-2055

Reference yield:

Dibenzyl-(1-benzyl-3-chloro-1,2,3,6-tetrahydro-pyridin-4-yl)-amine (210165-61-0) → 7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (210236-57-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / MeONa / 20 h / 20 °C

2: 89 percent / DIBAH / tetrahydrofuran / 1.) 60 deg C, 5 h, 2.) 20 deg C, 3 d

3: 50 percent / CHCl₃ / 1.) 50 deg C, 1.75 h, 2.) 20 deg C, 2 h

4: 74 percent / H₂O, HCl / CHCl₃ / 14 h / Ambient temperature

5: 80 percent / NEt₃ / acetonitrile / 5 h / 60 °C

6: 77 percent / H₂O, HCl, H₂ / 5percent Pd/C / ethanol / 20 h / 23 °C

With hydrogenchloride; water; hydrogen; sodium methylate; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; chloroform; acetonitrile;

DOI:10.1055/s-1998-2055

upstream raw materials:

7-((1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

Dibenzyl-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-amine

Dibenzyl-(1-benzyl-3-chloro-1,2,3,6-tetrahydro-pyridin-4-yl)-amine

1α,5α,6β-6-dibenzylamino-3-azabicyclo[3.1.0]hexane

Downstream raw materials:

7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid; compound with methanesulfonic acid