2-[(8S)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol

Base Information

Chemical Name:2-[(8S)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol
CAS No.:1363139-88-1
Molecular Formula:C₂₆H₂₅F₃N₄O₄
Molecular Weight:514.504
Hs Code.:

Synonyms:2-[(8S)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol

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Chemical Property of 2-[(8S)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol

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Technology Process of 2-[(8S)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol

There total 15 articles about 2-[(8S)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-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:

: 1363138-64-0
2-{3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}propan-2-ol

: 1363139-83-6
2-[(8R)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol

: 1363139-88-1
2-[(8S)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol

Guidance literature:: With chiralpak AD; In hexane; Resolution of racemate;
DOI:10.1016/j.bmc.2016.05.040

Reference yield:

: 1363138-64-0
2-{3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}propan-2-ol

: 1363139-88-1
2-[(8S)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol

Guidance literature:: With CHIRALCEL AD; Resolution of racemate;

Reference yield:

: 112704-79-7
2-fluoro-4-bromobenzoic acid

: 1363139-88-1
2-[(8S)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 47 h / 20 - 40 °C

2.1: diethyl ether; tetrahydrofuran / 3 h / 0 - 20 °C

3.1: trifluorormethanesulfonic acid; [bis(acetoxy)iodo]benzene / 0.5 h / 20 °C / Reflux

3.2: Reflux

4.1: zinc; zinc(II) cyanide; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1 h / 120 °C / Inert atmosphere

4.2: 4 h / 0 - 20 °C

4.3: 48 h / Reflux

5.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 20 °C

5.2: 16 h / -10 - 20 °C

6.1: 8-(3,4-dichlorophenyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine / acetonitrile / 16 h / 20 °C

6.2: 24 h / 20 °C / Reflux

7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / Cooling with ice

7.2: 0.33 h / Cooling with ice

8.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 - 100 °C

9.1: methylmagnesium bromide / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

10.1: CHIRALCEL AD / Resolution of racemate

With trifluorormethanesulfonic acid; [bis(acetoxy)iodo]benzene; 8-(3,4-dichlorophenyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine; methylmagnesium bromide; sodium hydride; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; zinc(II) cyanide; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; zinc; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile; mineral oil;