(5R,8S,9S)-9-amino-8-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

Base Information

Chemical Name:(5R,8S,9S)-9-amino-8-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate
CAS No.:1409943-97-0
Molecular Formula:C₂₇H₂₇F₂N₇O₃
Molecular Weight:535.553
Hs Code.:

(5R,8S,9S)-9-amino-8-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

Synonyms:(5R,8S,9S)-9-amino-8-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

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Chemical Property of (5R,8S,9S)-9-amino-8-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

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Technology Process of (5R,8S,9S)-9-amino-8-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

There total 15 articles about (5R,8S,9S)-9-amino-8-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-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: 69.0%

: 1409943-96-9
(5R,8S,9S)-9-(tert-butoxycarbonylamino)-8-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

: 1409943-97-0
(5R,8S,9S)-9-amino-8-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

Reference yield:

: 1409944-03-1
(S)-1,2-difluoro-3-(1-nitrohex-5-en-2-yl)benzene

: 1409943-97-0
(5R,8S,9S)-9-amino-8-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1.1: sodium methylate / methanol / 0.5 h / 0 °C / Inert atmosphere

1.2: 4 h / -60 - -20 °C

1.3: 18 h / 20 °C

2.1: titanium(IV) tetraethanolate / benzene; tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

3.1: lithium diisopropyl amide; n-butyllithium / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

3.2: 2 h / -75 °C

4.1: hydrogenchloride / 1,4-dioxane; methanol / 1 h / 20 °C

5.1: triethylamine / dichloromethane / 2 h / 20 °C

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

7.1: N-Methyldicyclohexylamine / bis(tri-t-butylphosphine)palladium⁽⁰⁾ / 1,4-dioxane / 2.02 h / 20 - 160 °C / Microwave irradiation; Inert atmosphere

8.1: ozone / dimethylsulfide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

9.1: water; sodium tetrahydroborate / methanol / 2 h / 20 °C

10.1: N,N-dimethyl-formamide; benzene / Inert atmosphere

10.2: -15 - 20 °C / Inert atmosphere

11.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; N-Methyldicyclohexylamine; water; sodium methylate; ozone; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) tetraethanolate; bis(tri-t-butylphosphine)palladium⁽⁰⁾; dimethylsulfide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 6.1: Grubbs' metathesis conditions / 7.1: Heck Reaction;

Reference yield:

: 1409944-04-2
(S)-2-(2, 3-difluorophenyl)hex-5-enal

: 1409943-97-0
(5R,8S,9S)-9-amino-8-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1.1: titanium(IV) tetraethanolate / benzene; tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

2.1: lithium diisopropyl amide; n-butyllithium / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

2.2: 2 h / -75 °C

3.1: hydrogenchloride / 1,4-dioxane; methanol / 1 h / 20 °C

4.1: triethylamine / dichloromethane / 2 h / 20 °C

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

6.1: N-Methyldicyclohexylamine / bis(tri-t-butylphosphine)palladium⁽⁰⁾ / 1,4-dioxane / 2.02 h / 20 - 160 °C / Microwave irradiation; Inert atmosphere

7.1: ozone / dimethylsulfide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

8.1: water; sodium tetrahydroborate / methanol / 2 h / 20 °C

9.1: N,N-dimethyl-formamide; benzene / Inert atmosphere

9.2: -15 - 20 °C / Inert atmosphere

10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; N-Methyldicyclohexylamine; water; ozone; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) tetraethanolate; bis(tri-t-butylphosphine)palladium⁽⁰⁾; dimethylsulfide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 5.1: Grubbs' metathesis conditions / 6.1: Heck Reaction;