1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-3-azetidinecarboxylic acid

Base Information

• Chemical Name: 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-3-azetidinecarboxylic acid
• CAS No.: 1344995-82-9
• Molecular Formula: C₂₇H₃₀N₄O₂S
• Molecular Weight: 474.627
• Mol file: 1344995-82-9.mol

Synonyms:1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-3-azetidinecarboxylic acid

Chemical Property of 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-3-azetidinecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-3-azetidinecarboxylic acid

There total 10 articles about 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-3-azetidinecarboxylic acid 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 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-3-azetidinecarboxylate (1344997-46-1) → 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-3-azetidinecarboxylic acid (1344995-82-9)

Guidance literature:

methyl 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-3-azetidinecarboxylate; With water; sodium hydroxide; In isopropyl alcohol; at 20 ℃; for 1h;

With hydrogenchloride; In water; isopropyl alcohol;

Reference yield:

methyl 3-iodo-4-hydroxybenzoate (15126-06-4) → 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-3-azetidinecarboxylic acid (1344995-82-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 12 h / 140 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 25 °C

3.1: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water / 12 h / 100 °C / Inert atmosphere

4.1: water; lithium hydroxide / methanol / 4 h / 25 °C

4.2: pH 5

5.1: trichlorophosphate / 3 h / 90 °C

5.2: pH 8 - 9 / Cooling with ice

6.1: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 3 h / 20 °C

7.1: potassium phosphate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; water / 0.17 h / 120 °C / Microwave irradiation; Sealed vessel; Inert atmosphere

8.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 0.17 h / 20 °C / Inert atmosphere

9.1: sodium acetate; acetic acid / ethanol / 0.17 h / 20 °C

10.1: sodium hydroxide; water / isopropyl alcohol / 1 h / 20 °C

With potassium phosphate; chloro-trimethyl-silane; tert.-butylnitrite; water; sodium acetate; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium iodide; sodium hydroxide; copper(ll) bromide; lithium hydroxide; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In methanol; ethanol; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; 3.1: Suzuki Coupling / 7.1: Suzuki Coupling;

Reference yield:

methyl 3-cyano-4-hydroxybenzoate (156001-68-2) → 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-3-azetidinecarboxylic acid (1344995-82-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 25 °C

2.1: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water / 12 h / 100 °C / Inert atmosphere

3.1: water; lithium hydroxide / methanol / 4 h / 25 °C

3.2: pH 5

4.1: trichlorophosphate / 3 h / 90 °C

4.2: pH 8 - 9 / Cooling with ice

5.1: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 3 h / 20 °C

6.1: potassium phosphate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; water / 0.17 h / 120 °C / Microwave irradiation; Sealed vessel; Inert atmosphere

7.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 0.17 h / 20 °C / Inert atmosphere

8.1: sodium acetate; acetic acid / ethanol / 0.17 h / 20 °C

9.1: sodium hydroxide; water / isopropyl alcohol / 1 h / 20 °C

With potassium phosphate; chloro-trimethyl-silane; tert.-butylnitrite; water; sodium acetate; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium iodide; sodium hydroxide; copper(ll) bromide; lithium hydroxide; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In methanol; ethanol; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; 2.1: Suzuki Coupling / 6.1: Suzuki Coupling;

upstream raw materials:

methyl 3-iodo-4-hydroxybenzoate

methyl 3-cyano-4-hydroxybenzoate

methyl 3-cyano-4-(((trifluoromethyl)sulfonyl)oxy)benzoate

3-cyano-4-(2-methylpropyl)benzoic acid