N-(3-methoxybenzyl)-6-methyl-4-(2-(((trans)-4-(methylsulfonamido)cyclohexyl)methyl)-2H-tetrazol-5-yl)picolinamide

Base Information

• Chemical Name: N-(3-methoxybenzyl)-6-methyl-4-(2-(((trans)-4-(methylsulfonamido)cyclohexyl)methyl)-2H-tetrazol-5-yl)picolinamide
• CAS No.: 1112171-09-1
• Molecular Formula: C₂₄H₃₁N₇O₄S
• Molecular Weight: 513.621

Synonyms:N-(3-methoxybenzyl)-6-methyl-4-(2-(((trans)-4-(methylsulfonamido)cyclohexyl)methyl)-2H-tetrazol-5-yl)picolinamide

Chemical Property of N-(3-methoxybenzyl)-6-methyl-4-(2-(((trans)-4-(methylsulfonamido)cyclohexyl)methyl)-2H-tetrazol-5-yl)picolinamide

Chemical Property:

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Technology Process of N-(3-methoxybenzyl)-6-methyl-4-(2-(((trans)-4-(methylsulfonamido)cyclohexyl)methyl)-2H-tetrazol-5-yl)picolinamide

There total 9 articles about N-(3-methoxybenzyl)-6-methyl-4-(2-(((trans)-4-(methylsulfonamido)cyclohexyl)methyl)-2H-tetrazol-5-yl)picolinamide 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: 24.0%

N-(3-methoxybenzyl)-4-(2-(((trans)-4-aminocyclohexyl)methyl)-2H-tetrazol-5-yl)-6-methylpicolinamide (1112171-08-0) + methanesulfonyl chloride (124-63-0) → N-(3-methoxybenzyl)-6-methyl-4-(2-(((trans)-4-(methylsulfonamido)cyclohexyl)methyl)-2H-tetrazol-5-yl)picolinamide (1112171-09-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

2-chloro-6-methylpyridine-4-carboxylic acid (25462-85-5) → N-(3-methoxybenzyl)-6-methyl-4-(2-(((trans)-4-(methylsulfonamido)cyclohexyl)methyl)-2H-tetrazol-5-yl)picolinamide (1112171-09-1)

Guidance literature:

Multi-step reaction with 9 steps

1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 15 h / 20 °C

2: dichloromethane / 15 h / 20 °C

3: trichlorophosphate / toluene / 15 h / 110 °C

4: triethylamine hydrochloride; sodium azide / toluene / 4 h / Reflux

5: triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate / 24 h / 100 °C / 6205.94 - 9826.07 Torr

6: 1 h / 100 °C / Inert atmosphere

7: di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 18 h

8: trifluoroacetic acid / dichloromethane / 2 h

9: triethylamine / dichloromethane / 2 h / 20 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; sodium azide; oxalyl dichloride; di-tert-butyl-diazodicarboxylate; palladium diacetate; triethylamine hydrochloride; triethylamine; trifluoroacetic acid; trichlorophosphate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/acs.jmedchem.5b01434

Reference yield:

2-chloro-6-methyl-4-pyridinecarbonyl chloride (26413-58-1) → N-(3-methoxybenzyl)-6-methyl-4-(2-(((trans)-4-(methylsulfonamido)cyclohexyl)methyl)-2H-tetrazol-5-yl)picolinamide (1112171-09-1)

Guidance literature:

Multi-step reaction with 8 steps

1: dichloromethane / 15 h / 20 °C

2: trichlorophosphate / toluene / 15 h / 110 °C

3: triethylamine hydrochloride; sodium azide / toluene / 4 h / Reflux

4: triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate / 24 h / 100 °C / 6205.94 - 9826.07 Torr

5: 1 h / 100 °C / Inert atmosphere

6: di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 18 h

7: trifluoroacetic acid / dichloromethane / 2 h

8: triethylamine / dichloromethane / 2 h / 20 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; sodium azide; di-tert-butyl-diazodicarboxylate; palladium diacetate; triethylamine hydrochloride; triethylamine; trifluoroacetic acid; trichlorophosphate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/acs.jmedchem.5b01434

upstream raw materials:

N-(3-methoxybenzyl)-4-(2-(((trans)-4-aminocyclohexyl)methyl)-2H-tetrazol-5-yl)-6-methylpicolinamide

methanesulfonyl chloride

2-chloro-6-methylpyridine-4-carboxylic acid

2-chloro-6-methyl-4-pyridinecarbonyl chloride

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