methyl N-[(10R,14S)-14-[2-chloro-N-({[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]carbamoyl}methyl)acetamido]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0^2,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate

Base Information

• Chemical Name: methyl N-[(10R,14S)-14-[2-chloro-N-({[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]carbamoyl}methyl)acetamido]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0^2,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate
• CAS No.: 1422511-20-3
• Molecular Formula: C₃₁H₂₉Cl₂F₄N₅O₅
• Molecular Weight: 698.501

Synonyms:methyl N-[(10R,14S)-14-[2-chloro-N-({[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]carbamoyl}methyl)acetamido]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0^2,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate

Chemical Property of methyl N-[(10R,14S)-14-[2-chloro-N-({[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]carbamoyl}methyl)acetamido]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0^2,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of methyl N-[(10R,14S)-14-[2-chloro-N-({[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]carbamoyl}methyl)acetamido]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0^2,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate

There total 20 articles about methyl N-[(10R,14S)-14-[2-chloro-N-({[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]carbamoyl}methyl)acetamido]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0^2,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate 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:

methyl N-[(10R,14S)-14-[({[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]carbamoyl}methyl)amino]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-5-yl]carbamate (1422511-19-0) + chloroacetyl chloride (79-04-9) → methyl N-[(10R,14S)-14-[2-chloro-N-({[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]carbamoyl}methyl)acetamido]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-5-yl]carbamate (1422511-20-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 ℃; for 0.166667h;

Reference yield:

2-bromo 5-nitroaniline (10403-47-1) → methyl N-[(10R,14S)-14-[2-chloro-N-({[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]carbamoyl}methyl)acetamido]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-5-yl]carbamate (1422511-20-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / dimethyl sulfoxide / 4.5 h / 80 °C / Inert atmosphere

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate / water; dimethyl sulfoxide / 4 h / 90 °C / Inert atmosphere

3.1: zinc; ammonium chloride / methanol / 2 h / 20 °C / Sealed tube

4.1: pyridine / dichloromethane / 2 h / -78 °C

5.1: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C

6.1: triethylamine / dichloromethane / 3 h / 20 °C

7.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / ethyl acetate / 7 h / -10 - 0 °C

8.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 40 °C / Inert atmosphere

8.2: 6 h / 40 °C / Inert atmosphere

9.1: palladium 10% on activated carbon; hydrogen / methanol / 20 h / 2585.81 Torr / Inert atmosphere

10.1: hydrogenchloride / 1,4-dioxane / 1 h

11.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 70 °C / Sealed tube

12.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.17 h / 0 °C

With pyridine; hydrogenchloride; potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium 10% on activated carbon; hydrogen; potassium acetate; ammonium chloride; toluene-4-sulfonic acid; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

2‐(5,5‐dimethyl‐1,3,2‐dioxaborinan‐2‐yl)‐5‐nitroaniline (1329166-69-9) → methyl N-[(10R,14S)-14-[2-chloro-N-({[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]carbamoyl}methyl)acetamido]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-5-yl]carbamate (1422511-20-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate / water; dimethyl sulfoxide / 4 h / 90 °C / Inert atmosphere

2.1: zinc; ammonium chloride / methanol / 2 h / 20 °C / Sealed tube

3.1: pyridine / dichloromethane / 2 h / -78 °C

4.1: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C

5.1: triethylamine / dichloromethane / 3 h / 20 °C

6.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / ethyl acetate / 7 h / -10 - 0 °C

7.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 40 °C / Inert atmosphere

7.2: 6 h / 40 °C / Inert atmosphere

8.1: palladium 10% on activated carbon; hydrogen / methanol / 20 h / 2585.81 Torr / Inert atmosphere

9.1: hydrogenchloride / 1,4-dioxane / 1 h

10.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 70 °C / Sealed tube

11.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.17 h / 0 °C

With pyridine; hydrogenchloride; potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium 10% on activated carbon; hydrogen; ammonium chloride; toluene-4-sulfonic acid; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

2-methylbut-3-enoic acid

2-bromo 5-nitroaniline

2‐(5,5‐dimethyl‐1,3,2‐dioxaborinan‐2‐yl)‐5‐nitroaniline

(R)-2-methylbut-3-enoic acid

Downstream raw materials:

methyl N-[(10R)-14-{4-[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]-2,5-dioxopiperazin-1-yl}-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0^2,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate trifluoroacetate

methyl N-[(10R)-14-{4-[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]-2,5-dioxopiperazin-1-yl}-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate trifluoroacetate

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