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

Base Information

• Chemical Name: methyl 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-3-azetidinecarboxylate
• CAS No.: 1344997-46-1
• Molecular Formula: C₂₈H₃₂N₄O₂S
• Molecular Weight: 488.654
• Mol file: 1344997-46-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about methyl 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-3-azetidinecarboxylate 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:

5-{5-[2-ethyl-3-(2-oxoethyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-(2-methylpropyl)benzonitrile (1344997-45-0) + methyl azetidine-3-carboxylate (343238-58-4) → 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)

Guidance literature:

5-{5-[2-ethyl-3-(2-oxoethyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-(2-methylpropyl)benzonitrile; methyl azetidine-3-carboxylate; With sodium acetate; acetic acid; In ethanol; at 20 ℃; for 0.166667h;

With sodium tris(acetoxy)borohydride; In dichloromethane;

Reference yield:

methyl 3-iodo-4-hydroxybenzoate (15126-06-4) → 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)

Guidance literature:

Multi-step reaction with 9 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

With potassium phosphate; chloro-trimethyl-silane; tert.-butylnitrite; water; sodium acetate; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium iodide; 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; toluene; acetonitrile; 3.1: Suzuki Coupling / 7.1: Suzuki Coupling;

Reference yield:

methyl 3-cyano-4-hydroxybenzoate (156001-68-2) → 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)

Guidance literature:

Multi-step reaction with 8 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

With potassium phosphate; chloro-trimethyl-silane; tert.-butylnitrite; water; sodium acetate; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium iodide; 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; 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

Downstream raw materials:

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

Refernces

• 1、 -. "COMPOUNDS AS AGONISTS OF S1P1 RECEPTORS". . . Retrieved 2011/11/12.