methyl 4-cyano-2-{[(3R,6R)-6-methyl-1-{[2-(2H-1,2,3,4-tetrazol-2-yl)phenyl]carbonyl}piperidin-3-yl]oxy}pyridine-3-carboxylate

Base Information

• Chemical Name: methyl 4-cyano-2-{[(3R,6R)-6-methyl-1-{[2-(2H-1,2,3,4-tetrazol-2-yl)phenyl]carbonyl}piperidin-3-yl]oxy}pyridine-3-carboxylate
• CAS No.: 1604795-11-0
• Molecular Formula: C₂₂H₂₁N₇O₄
• Molecular Weight: 447.453
• Mol file: 1604795-11-0.mol

Synonyms:methyl 4-cyano-2-{[(3R,6R)-6-methyl-1-{[2-(2H-1,2,3,4-tetrazol-2-yl)phenyl]carbonyl}piperidin-3-yl]oxy}pyridine-3-carboxylate

Chemical Property of methyl 4-cyano-2-{[(3R,6R)-6-methyl-1-{[2-(2H-1,2,3,4-tetrazol-2-yl)phenyl]carbonyl}piperidin-3-yl]oxy}pyridine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-cyano-2-{[(3R,6R)-6-methyl-1-{[2-(2H-1,2,3,4-tetrazol-2-yl)phenyl]carbonyl}piperidin-3-yl]oxy}pyridine-3-carboxylate

There total 14 articles about methyl 4-cyano-2-{[(3R,6R)-6-methyl-1-{[2-(2H-1,2,3,4-tetrazol-2-yl)phenyl]carbonyl}piperidin-3-yl]oxy}pyridine-3-carboxylate 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 4-cyano-2-{[(3R,6R)-6-methylpiperidin-3-yl]oxy}pyridine-3-carboxylate hydrochloride + 2-(2H-tetrazol-2-yl)benzoic acid (1431473-20-9) → methyl 4-cyano-2-{[(3R,6R)-6-methyl-1-{[2-(2H-1,2,3,4-tetrazol-2-yl)phenyl]carbonyl}piperidin-3-yl]oxy}pyridine-3-carboxylate (1604795-11-0)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 50 ℃; for 72h;

Reference yield:

benzyl (2R,5R)-5-hydroxy-2-methylpiperidine-1-carboxylate (1431473-04-9) → methyl 4-cyano-2-{[(3R,6R)-6-methyl-1-{[2-(2H-1,2,3,4-tetrazol-2-yl)phenyl]carbonyl}piperidin-3-yl]oxy}pyridine-3-carboxylate (1604795-11-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / Inert atmosphere

2.1: sodium hydride / dimethyl sulfoxide

2.2: 48 h / 40 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C

3.2: 20 °C

4.1: zinc; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / 1,4-dioxane / 0.67 h / 120 °C / Inert atmosphere; Irradiation

5.1: hydrogenchloride

6.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 72 h / 50 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; bis(tri-t-butylphosphine)palladium⁽⁰⁾; palladium 10% on activated carbon; hydrogen; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; zinc; In 1,4-dioxane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

(±)-trans-6-methylpiperidin-3-ol monohydrochloride → methyl 4-cyano-2-{[(3R,6R)-6-methyl-1-{[2-(2H-1,2,3,4-tetrazol-2-yl)phenyl]carbonyl}piperidin-3-yl]oxy}pyridine-3-carboxylate (1604795-11-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C

2.2: -78 - 20 °C

3.1: lithium borohydride; methanol / tetrahydrofuran / 0.5 h / -10 - -5 °C

4.1: 4-(N,N-Dimethylamino)triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / -25 - 20 °C / Inert atmosphere

5.1: sodium hydroxide; water / methanol; tetrahydrofuran

6.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / Inert atmosphere

7.1: sodium hydride / dimethyl sulfoxide

7.2: 48 h / 40 °C

8.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C

8.2: 20 °C

9.1: zinc; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / 1,4-dioxane / 0.67 h / 120 °C / Inert atmosphere; Irradiation

10.1: hydrogenchloride

11.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 72 h / 50 °C

With hydrogenchloride; methanol; lithium borohydride; 1-hydroxy-7-aza-benzotriazole; oxalyl dichloride; bis(tri-t-butylphosphine)palladium⁽⁰⁾; palladium 10% on activated carbon; water; hydrogen; sodium hydride; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; zinc; diethylazodicarboxylate; 4-(N,N-Dimethylamino)triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; 2.1: |Swern Oxidation / 3.1: |Swern Oxidation;

upstream raw materials:

benzyl (2R,5R)-5-hydroxy-2-methylpiperidine-1-carboxylate

(R)-2-Hydroxy-(R)-5-methylpiperidine-(R)-amine-N-oxide

tert-butyl (2R,5R)-5-hydroxy-2-methylpiperidine-1-carboxylate

(R)-2-(but-3-en-1-yl)oxirane