1-(2,4-difluorophenyl)-7-[(1α,5α,6α)-6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Base Information

Chemical Name:1-(2,4-difluorophenyl)-7-[(1α,5α,6α)-6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
CAS No.:925457-08-5
Molecular Formula:C₂₇H₂₆F₃N₃O₆
Molecular Weight:545.515
Hs Code.:

1-(2,4-difluorophenyl)-7-[(1α,5α,6α)-6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

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Chemical Property of 1-(2,4-difluorophenyl)-7-[(1α,5α,6α)-6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

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Technology Process of 1-(2,4-difluorophenyl)-7-[(1α,5α,6α)-6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

There total 14 articles about 1-(2,4-difluorophenyl)-7-[(1α,5α,6α)-6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid 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: 73.0%

: (1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline-carboxylato-O₃,O₄)difluoro-boron

: 134575-17-0
tert-butyl (1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate

: 925457-08-5
1-(2,4-difluorophenyl)-7-[(1α,5α,6α)-6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Guidance literature:: In acetonitrile; for 168000h; Heating;
DOI:10.1016/j.ejmech.2006.07.003

Reference yield:

: 134575-13-6
(1α,5α,6α)-6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane

: 925457-08-5
1-(2,4-difluorophenyl)-7-[(1α,5α,6α)-6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: aq. K₂CO₃ / dioxane / 15 h / 20 °C

2.1: CrO₃; aq. H₂SO₄ / acetone / 2 h / 0 - 20 °C

3.1: NEt₃; (PhO)2P(O)N₃ / 44 h / Heating

4.1: H₂ / Pd/C / methanol / 5 h / 0 °C

5.1: boron trifluoride etherate / tetrahydrofuran / Heating

5.2: acetonitrile / 168 h / Heating

With chromium(VI) oxide; sulfuric acid; diphenyl phosphoryl azide; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; acetone; 2.1: Jones oxidation;
DOI:10.1016/j.bmcl.2004.03.070

Reference yield:

: 134575-07-8
(1α,5α,6α)-6-hydroxymethyl-3-benzyl-3-aza-bicyclo[3.1.0]hexane

: 925457-08-5
1-(2,4-difluorophenyl)-7-[(1α,5α,6α)-6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: H₂ / Pd/C / methanol / 23 h / 0 °C

2.1: aq. K₂CO₃ / dioxane / 15 h / 20 °C

3.1: CrO₃; aq. H₂SO₄ / acetone / 2 h / 0 - 20 °C

4.1: NEt₃; (PhO)2P(O)N₃ / 44 h / Heating

5.1: H₂ / Pd/C / methanol / 5 h / 0 °C

6.1: boron trifluoride etherate / tetrahydrofuran / Heating

6.2: acetonitrile / 168 h / Heating

With chromium(VI) oxide; sulfuric acid; diphenyl phosphoryl azide; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; acetone; 3.1: Jones oxidation;
DOI:10.1016/j.bmcl.2004.03.070