2-(4-((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-4-hexyn-2-ol

Base Information

Chemical Name:2-(4-((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-4-hexyn-2-ol
CAS No.:1589535-24-9
Molecular Formula:C₂₄H₂₅F₃N₄O₃S
Molecular Weight:506.549
Hs Code.:

Synonyms:2-(4-((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-4-hexyn-2-ol

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Chemical Property of 2-(4-((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-4-hexyn-2-ol

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Technology Process of 2-(4-((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-4-hexyn-2-ol

There total 21 articles about 2-(4-((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-4-hexyn-2-ol 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: 90.0%

: 1572928-70-1
tert-butyl (5-(((3S)-4-(4-(1-hydroxy-1-(trifluoromethyl)-3-pentyn-1-yl)phenyl)-3-(1-propyn-1-yl)-1-piperazinyl)sulfonyl)-2-pyridinyl)carbamate

: 1589535-24-9
2-(4-((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-4-hexyn-2-ol

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/jm5000497

Reference yield:

: 1361224-49-8
benzyl (2-((tert-butoxycarbonyl)amino)ethyl)(2-oxo-3-pentyn-1-yl)-carbamate

: 1589535-24-9
2-(4-((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-4-hexyn-2-ol

Guidance literature:: Multi-step reaction with 13 steps

1.1: trifluoroacetic acid / dichloromethane / -10 - 20 °C

2.1: sodium tris(acetoxy)borohydride / dichloromethane / 2.17 h / 20 °C

3.1: triethylamine; dmap / dichloromethane / 0.5 h / 20 °C

4.1: Chiralpak^?ADH column / ethanol / Supercritical conditions; Resolution of racemate

5.1: trifluoroacetic acid / dichloromethane / 0.67 h / 20 °C

6.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; ruphos / 1,4-dioxane / 80 - 100 °C / Inert atmosphere

7.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 20 °C

8.1: triethylamine / dichloromethane / 0.08 h / 20 °C

8.2: 20 °C

9.1: trifluoroacetic acid; p-toluenesulfonyl chloride / dichloromethane / 2 h / 50 °C / Inert atmosphere

10.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

10.2: 20.17 h / -78 - 20 °C

11.1: potassium carbonate / methanol / 2 h / 20 °C

12.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 °C

12.2: 2 h / 0 - 20 °C

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

With dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; trifluorormethanesulfonic acid; sodium tris(acetoxy)borohydride; potassium carbonate; triethylamine; p-toluenesulfonyl chloride; trifluoroacetic acid; sodium t-butanolate; ruphos; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane;
DOI:10.1021/jm5000497

Reference yield:

: 1361224-50-1
benzyl 3-(propan-1-yn-1-yl)piperazine-1-carboxylate

: 1589535-24-9
2-(4-((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-4-hexyn-2-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: triethylamine; dmap / dichloromethane / 0.5 h / 20 °C

2.1: Chiralpak^?ADH column / ethanol / Supercritical conditions; Resolution of racemate

3.1: trifluoroacetic acid / dichloromethane / 0.67 h / 20 °C

4.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; ruphos / 1,4-dioxane / 80 - 100 °C / Inert atmosphere

5.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 20 °C

6.1: triethylamine / dichloromethane / 0.08 h / 20 °C

6.2: 20 °C

7.1: trifluoroacetic acid; p-toluenesulfonyl chloride / dichloromethane / 2 h / 50 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: 20.17 h / -78 - 20 °C

9.1: potassium carbonate / methanol / 2 h / 20 °C

10.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 °C

10.2: 2 h / 0 - 20 °C

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

With dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; trifluorormethanesulfonic acid; potassium carbonate; triethylamine; p-toluenesulfonyl chloride; trifluoroacetic acid; sodium t-butanolate; ruphos; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane;
DOI:10.1021/jm5000497