(5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-[(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl]methanone

Base Information

• Chemical Name: (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-[(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl]methanone
• CAS No.: 1597522-60-5
• Molecular Formula: C₂₄H₂₁F₃N₆O₄
• Molecular Weight: 514.464

Synonyms:(5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-[(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl]methanone

Chemical Property of (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-[(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl]methanone

Chemical Property:

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Technology Process of (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-[(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl]methanone

There total 8 articles about (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-[(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl]methanone 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: 89.0%

5-methoxy-4-methyl-2-(2H-1 ,2,3-triazol-2-yl)benzoic acid (1429776-75-9) + 3-(S)-pyrrolidin-2-yl-5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazole → (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-[(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl]methanone (1597522-60-5)

Guidance literature:

5-methoxy-4-methyl-2-(2H-1 ,2,3-triazol-2-yl)benzoic acid; With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.333333h; Inert atmosphere;

3-(S)-pyrrolidin-2-yl-5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazole; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/cmdc.201900242

Reference yield:

tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate (228244-04-0) → (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-[(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl]methanone (1597522-60-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydroxylamine hydrochloride; sodium carbonate / methanol / 1 h / 70 °C / Inert atmosphere

2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C / Inert atmosphere

2.2: 1.5 h / 20 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

4.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

With hydroxylamine hydrochloride; sodium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1002/cmdc.201900242

Reference yield:

(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidine-1-carboxylic acid tert-butyl ester → (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-[(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl]methanone (1597522-60-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1002/cmdc.201900242

upstream raw materials:

2-bromo-5-methoxy-4-methyl-benzoic acid

3-methoxy-p-toluic acid

5-methoxy-4-methyl-2-(2H-1 ,2,3-triazol-2-yl)benzoic acid

tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate

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