N-((1s,4s)-4-(1,5-dimethyl-1H-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(4'-(2-hydroxyethyl)biphenyl-3-yloxy)nicotinamide

Base Information

Chemical Name:N-((1s,4s)-4-(1,5-dimethyl-1H-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(4'-(2-hydroxyethyl)biphenyl-3-yloxy)nicotinamide
CAS No.:1197291-39-6
Molecular Formula:C₃₂H₃₄FN₅O₄
Molecular Weight:571.651
Hs Code.:

Synonyms:N-((1s,4s)-4-(1,5-dimethyl-1H-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(4'-(2-hydroxyethyl)biphenyl-3-yloxy)nicotinamide

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Chemical Property of N-((1s,4s)-4-(1,5-dimethyl-1H-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(4'-(2-hydroxyethyl)biphenyl-3-yloxy)nicotinamide

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Technology Process of N-((1s,4s)-4-(1,5-dimethyl-1H-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(4'-(2-hydroxyethyl)biphenyl-3-yloxy)nicotinamide

There total 7 articles about N-((1s,4s)-4-(1,5-dimethyl-1H-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(4'-(2-hydroxyethyl)biphenyl-3-yloxy)nicotinamide 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: 70.0%

: 4654-39-1
4-bromophenethanol

: 1197291-22-7
N-((1s,4s)-4-(1,5-dimethyl-1H-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)nicotinamide

: 1197291-39-6
N-((1s,4s)-4-(1,5-dimethyl-1H-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(4'-(2-hydroxyethyl)biphenyl-3-yloxy)nicotinamide

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In tetrahydrofuran; water; at 70 ℃; for 18h; Inert atmosphere;
DOI:10.1021/jm5001216

Reference yield:

: 1196806-69-5
tert-butyl N-[(1s,4s)-4-[5-fluoro-2-(3-iodophenoxy)nicotinamido]cyclohexyl]carbamate

: 1197291-39-6
N-((1s,4s)-4-(1,5-dimethyl-1H-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(4'-(2-hydroxyethyl)biphenyl-3-yloxy)nicotinamide

Guidance literature:: Multi-step reaction with 4 steps

1: hydrogenchloride / dichloromethane; 1,4-dioxane / 16 h / 18 - 25 °C / Inert atmosphere

2: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / acetonitrile; tetrahydrofuran / 20 h / 18 - 25 °C / Inert atmosphere

3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / dimethyl sulfoxide / 20 h / 80 °C / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water / 18 h / 70 °C / Inert atmosphere

With hydrogenchloride; 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium carbonate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; acetonitrile; 4: |Suzuki Coupling;
DOI:10.1021/jm5001216

Reference yield:

: 38186-88-8
2-chloro-5-fluoronicotinic acid

: 1197291-39-6
N-((1s,4s)-4-(1,5-dimethyl-1H-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(4'-(2-hydroxyethyl)biphenyl-3-yloxy)nicotinamide

Guidance literature:: Multi-step reaction with 6 steps

1: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / acetonitrile; tetrahydrofuran / 0 - 25 °C / Inert atmosphere

2: caesium carbonate / N,N-dimethyl-formamide / 48 h / 60 °C / Inert atmosphere

3: hydrogenchloride / dichloromethane; 1,4-dioxane / 16 h / 18 - 25 °C / Inert atmosphere

4: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / acetonitrile; tetrahydrofuran / 20 h / 18 - 25 °C / Inert atmosphere

5: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / dimethyl sulfoxide / 20 h / 80 °C / Inert atmosphere

6: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water / 18 h / 70 °C / Inert atmosphere

With hydrogenchloride; 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium carbonate; caesium carbonate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 6: |Suzuki Coupling;
DOI:10.1021/jm5001216