3-chloro-5-{[6-chloro-2-fluoro-3-({5-[4-methyl-2-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-1,3-thiazol-5-yl]-1,3,4-oxadiazol-2-yl}methyl)phenyl]oxy}benzonitrile

Base Information

• Chemical Name: 3-chloro-5-{[6-chloro-2-fluoro-3-({5-[4-methyl-2-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-1,3-thiazol-5-yl]-1,3,4-oxadiazol-2-yl}methyl)phenyl]oxy}benzonitrile
• CAS No.: 1094342-50-3
• Molecular Formula: C₂₈H₂₅Cl₂FN₄O₅S
• Molecular Weight: 619.501
• Mol file: 1094342-50-3.mol

Synonyms:3-chloro-5-{[6-chloro-2-fluoro-3-({5-[4-methyl-2-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-1,3-thiazol-5-yl]-1,3,4-oxadiazol-2-yl}methyl)phenyl]oxy}benzonitrile

Chemical Property of 3-chloro-5-{[6-chloro-2-fluoro-3-({5-[4-methyl-2-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-1,3-thiazol-5-yl]-1,3,4-oxadiazol-2-yl}methyl)phenyl]oxy}benzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-chloro-5-{[6-chloro-2-fluoro-3-({5-[4-methyl-2-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-1,3-thiazol-5-yl]-1,3,4-oxadiazol-2-yl}methyl)phenyl]oxy}benzonitrile

There total 16 articles about 3-chloro-5-{[6-chloro-2-fluoro-3-({5-[4-methyl-2-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-1,3-thiazol-5-yl]-1,3,4-oxadiazol-2-yl}methyl)phenyl]oxy}benzonitrile 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:

4-methyl-2-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-1,3-thiazole-5-carboxylic acid (1094346-23-2) + 2-{4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}acetohydrazide (1093987-89-3) → 3-chloro-5-{[6-chloro-2-fluoro-3-({5-[4-methyl-2-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-1,3-thiazol-5-yl]-1,3,4-oxadiazol-2-yl}methyl)phenyl]oxy}benzonitrile (1094342-50-3)

Guidance literature:

4-methyl-2-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-1,3-thiazole-5-carboxylic acid; 2-{4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}acetohydrazide; With N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; at 20 ℃; for 3h;

With Burgess Reagent; In tetrahydrofuran; at 20 ℃; for 72h;

Reference yield:

2-<(S)-2,2-dimethyl-1,3-dioxolane-4-yl>-2-propanol (86562-71-2) → 3-chloro-5-{[6-chloro-2-fluoro-3-({5-[4-methyl-2-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-1,3-thiazol-5-yl]-1,3,4-oxadiazol-2-yl}methyl)phenyl]oxy}benzonitrile (1094342-50-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridinium p-toluenesulfonate / methanol; water / 5 h / Reflux

2.1: pyridine / 16.5 h / -10 - -5 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / acetone / 72 h / 20 °C

4.1: toluene-4-sulfonic acid; 2,2-dimethoxy-propane / toluene / 1 h / 50 °C

4.2: 2 h / 90 °C

5.1: caesium carbonate / 1,1'-binaphthalen-2-yl[bis(1,1-dimethylethyl)]phosphane; palladium diacetate / toluene / 6 h / 100 °C / Inert atmosphere

6.1: lithium hydroxide / tetrahydrofuran / 2 h / 20 °C

6.2: 2 h / 20 °C

7.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 3 h / 20 °C

7.2: 72 h / 20 °C

With pyridine; pyridinium p-toluenesulfonate; caesium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 2,2-dimethoxy-propane; HATU; lithium hydroxide; 1,1'-binaphthalen-2-yl[bis(1,1-dimethylethyl)]phosphane; palladium diacetate; In tetrahydrofuran; methanol; water; acetone; toluene;

Reference yield:

S(-)methyl-3 butanetriol-1,2,3 (86562-72-3) → 3-chloro-5-{[6-chloro-2-fluoro-3-({5-[4-methyl-2-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-1,3-thiazol-5-yl]-1,3,4-oxadiazol-2-yl}methyl)phenyl]oxy}benzonitrile (1094342-50-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / 16.5 h / -10 - -5 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / acetone / 72 h / 20 °C

3.1: toluene-4-sulfonic acid; 2,2-dimethoxy-propane / toluene / 1 h / 50 °C

3.2: 2 h / 90 °C

4.1: caesium carbonate / 1,1'-binaphthalen-2-yl[bis(1,1-dimethylethyl)]phosphane; palladium diacetate / toluene / 6 h / 100 °C / Inert atmosphere

5.1: lithium hydroxide / tetrahydrofuran / 2 h / 20 °C

5.2: 2 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 3 h / 20 °C

6.2: 72 h / 20 °C

With pyridine; caesium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 2,2-dimethoxy-propane; HATU; lithium hydroxide; 1,1'-binaphthalen-2-yl[bis(1,1-dimethylethyl)]phosphane; palladium diacetate; In tetrahydrofuran; acetone; toluene;

upstream raw materials:

3,5-dichlorobenzonitrile

3-chloro-5-methoxybenzonitrile

3-chloro-5-hydroxybenzonitrile

3-chloro-5-[(2,3-difluoro-6-nitrophenyl)oxy]benzonitrile

Downstream raw materials:

3-chloro-5-[(6-chloro-2-fluoro-3-{[5-(4-methyl-2-oxo-2,3-dihydro-1,3-thiazol-5-yl)-1,3,4-oxadiazol-2-yl]methyl}phenyl)oxy]benzonitrile

Refernces