Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Base Information

• Chemical Name: Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate
• CAS No.: 171176-56-0
• Molecular Formula: C₂₂H₁₉F₃N₄O₃
• Molecular Weight: 444.413
• Mol file: 171176-56-0.mol

Synonyms:Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Chemical Property of Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

There total 7 articles about Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 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: 87.0%

Ethyl (1α,5α,6α)-7-(6-nitro-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (171176-55-9) → Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (171176-56-0)

Guidance literature:

With Raney nickel A-5000; hydrazine hydrate; In tetrahydrofuran; at 25 ℃; for 1.5h;

DOI:10.1039/a910340f

Reference yield:

(1α,5α,6α)-3-N-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane (151860-16-1) → Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (171176-56-0)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂; H₂O / 10percent Pd/C / propan-2-ol / 24 h / 50 °C / 2660.18 Torr

2: Et₃N / methanol / 3 h / 50 °C

With water; hydrogen; triethylamine; 10percent Pd/C; In methanol; isopropyl alcohol; 1: Reduction / 2: Substitution;

DOI:10.1039/a910340f

Reference yield:

(1α,5α,6α)-3-N-benzyl-6-nitro-2,4-dioxo-3-azabicyclo[3.1.0]hexane (151860-15-0) → Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (171176-56-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / NaBH₄; BF₃*THF / tetrahydrofuran / 3 h / 40 °C

2: H₂; H₂O / 10percent Pd/C / propan-2-ol / 24 h / 50 °C / 2660.18 Torr

3: Et₃N / methanol / 3 h / 50 °C

With sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex; water; hydrogen; triethylamine; 10percent Pd/C; In tetrahydrofuran; methanol; isopropyl alcohol; 1: Reduction / 2: Reduction / 3: Substitution;

DOI:10.1039/a910340f

upstream raw materials:

ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

(1α,5α,6α)-6-amino-3-azabicyclo[3.1.0]hexane

Ethyl (1α,5α,6α)-7-(6-nitro-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

(1α,5α,6α)-3-N-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane

Downstream raw materials:

trovafloxacin mesylate