5-chloro-N-[4-fluoro-3-[(1S,3S,6S)-3-methyl-5-thioxo-4-azabicyclo[4.1.0]heptan-3-yl]phenyl]pyridine-2-carboxamide

Base Information

Chemical Name:5-chloro-N-[4-fluoro-3-[(1S,3S,6S)-3-methyl-5-thioxo-4-azabicyclo[4.1.0]heptan-3-yl]phenyl]pyridine-2-carboxamide
CAS No.:1446318-62-2
Molecular Formula:C₁₉H₁₇ClFN₃OS
Molecular Weight:389.881
Hs Code.:

Synonyms:5-chloro-N-[4-fluoro-3-[(1S,3S,6S)-3-methyl-5-thioxo-4-azabicyclo[4.1.0]heptan-3-yl]phenyl]pyridine-2-carboxamide

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Chemical Property of 5-chloro-N-[4-fluoro-3-[(1S,3S,6S)-3-methyl-5-thioxo-4-azabicyclo[4.1.0]heptan-3-yl]phenyl]pyridine-2-carboxamide

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Technology Process of 5-chloro-N-[4-fluoro-3-[(1S,3S,6S)-3-methyl-5-thioxo-4-azabicyclo[4.1.0]heptan-3-yl]phenyl]pyridine-2-carboxamide

There total 12 articles about 5-chloro-N-[4-fluoro-3-[(1S,3S,6S)-3-methyl-5-thioxo-4-azabicyclo[4.1.0]heptan-3-yl]phenyl]pyridine-2-carboxamide 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: 100.0%

: 86873-60-1
5-chloropicolinic acid

: 1446318-61-1
(1S,3S,6S)-3-(5-amino-2-fluoro-phenyl)-3-methyl-4-azabicyclo[4.1.0]heptane-5-thione

: 1446318-62-2
5-chloro-N-[4-fluoro-3-[(1S,3S,6S)-3-methyl-5-thioxo-4-azabicyclo[4.1.0]heptan-3-yl]phenyl]pyridine-2-carboxamide

Guidance literature:: 5-chloropicolinic acid; With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 23 ℃; for 0.5h;

(1S,3S,6S)-3-(5-amino-2-fluoro-phenyl)-3-methyl-4-azabicyclo[4.1.0]heptane-5-thione; In dichloromethane; at 23 ℃; for 2h;
DOI:10.1016/j.bmcl.2013.05.003

Reference yield:

: 1446318-55-3
N-[(1S)-1-(5-bromo-2-fluoro-phenyl)-1-methyl-but-3-enyl]-N-[(4-methoxyphenyl)methyl] prop-2-enamide

: 1446318-62-2
5-chloro-N-[4-fluoro-3-[(1S,3S,6S)-3-methyl-5-thioxo-4-azabicyclo[4.1.0]heptan-3-yl]phenyl]pyridine-2-carboxamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Inert atmosphere; Heating

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / 0 °C

2.2: 0.75 h / 50 - 55 °C

3.1: methoxybenzene; trifluorormethanesulfonic acid; trifluoroacetic acid / 18 h / 70 °C

4.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium t-butanolate; tert-butyl XPhos / toluene / 19 h / 105 °C / Inert atmosphere; Sealed tube

5.1: Lawessons reagent / 1,4-dioxane / 2.5 h / 80 °C

6.1: hydrogenchloride / 1,4-dioxane; water / 0.5 h / 23 °C

7.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 23 °C

7.2: 2 h / 23 °C

With Lawessons reagent; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; n-butyllithium; trifluorormethanesulfonic acid; methoxybenzene; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; sodium t-butanolate; tert-butyl XPhos; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; toluene;
DOI:10.1016/j.bmcl.2013.05.003

Reference yield:

: 1446318-54-2
[(S)-1-(5-bromo-2-fluoro-phenyl)-1-methyl-but-3-enyl]-(4-methoxy-benzyl)-amine

: 1446318-62-2
5-chloro-N-[4-fluoro-3-[(1S,3S,6S)-3-methyl-5-thioxo-4-azabicyclo[4.1.0]heptan-3-yl]phenyl]pyridine-2-carboxamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydrogencarbonate / dichloromethane; water / 2.5 h / 0 - 23 °C

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Inert atmosphere; Heating

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / 0 °C

3.2: 0.75 h / 50 - 55 °C

4.1: methoxybenzene; trifluorormethanesulfonic acid; trifluoroacetic acid / 18 h / 70 °C

5.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium t-butanolate; tert-butyl XPhos / toluene / 19 h / 105 °C / Inert atmosphere; Sealed tube

6.1: Lawessons reagent / 1,4-dioxane / 2.5 h / 80 °C

7.1: hydrogenchloride / 1,4-dioxane; water / 0.5 h / 23 °C

8.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 23 °C

8.2: 2 h / 23 °C

With Lawessons reagent; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; n-butyllithium; trifluorormethanesulfonic acid; sodium hydrogencarbonate; methoxybenzene; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; sodium t-butanolate; tert-butyl XPhos; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; toluene;
DOI:10.1016/j.bmcl.2013.05.003