tert-butyl(1r,4r)-4-(7-(methoxycarbonyl)-5-bromo-1,6-naphthyridin-8-amino)cyclohexyl carbamate

Base Information

• Chemical Name: tert-butyl(1r,4r)-4-(7-(methoxycarbonyl)-5-bromo-1,6-naphthyridin-8-amino)cyclohexyl carbamate
• CAS No.: 1223081-79-5
• Molecular Formula: C₂₁H₂₇BrN₄O₄
• Molecular Weight: 479.374
• Mol file: 1223081-79-5.mol

Synonyms:tert-butyl(1r,4r)-4-(7-(methoxycarbonyl)-5-bromo-1,6-naphthyridin-8-amino)cyclohexyl carbamate

Chemical Property of tert-butyl(1r,4r)-4-(7-(methoxycarbonyl)-5-bromo-1,6-naphthyridin-8-amino)cyclohexyl carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl(1r,4r)-4-(7-(methoxycarbonyl)-5-bromo-1,6-naphthyridin-8-amino)cyclohexyl carbamate

There total 8 articles about tert-butyl(1r,4r)-4-(7-(methoxycarbonyl)-5-bromo-1,6-naphthyridin-8-amino)cyclohexyl carbamate 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: 78.0%

methyl 5-bromo-8-p-toluenesulfonyloxy-1,6-naphthyridine-7-carboxylate (410545-60-7) + trans-N-Boc-1,4-cyclohexanediamine (177906-48-8) → tert-butyl(1r,4r)-4-(7-(methoxycarbonyl)-5-bromo-1,6-naphthyridin-8-amino)cyclohexyl carbamate (1223081-79-5)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 8h; Reflux;

Reference yield:

5-bromo-8-hydroxy-[1,6]naphthyridine-7-carboxylic acid methyl ester (410544-37-5) → tert-butyl(1r,4r)-4-(7-(methoxycarbonyl)-5-bromo-1,6-naphthyridin-8-amino)cyclohexyl carbamate (1223081-79-5)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / Inert atmosphere; Reflux

2: triethylamine / tetrahydrofuran / Inert atmosphere; Reflux

With triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c2ob26710a

Reference yield:

Pyridine-2,3-dicarboxylic anhydride (699-98-9) → tert-butyl(1r,4r)-4-(7-(methoxycarbonyl)-5-bromo-1,6-naphthyridin-8-amino)cyclohexyl carbamate (1223081-79-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 16 h / Reflux

2: thionyl chloride / Reflux

3: sodium tetrahydroborate / tetrahydrofuran / 4 h / 0 °C

4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

5: methanol / 3 h / 0 - 20 °C

6: N-Bromosuccinimide / dichloromethane

7: triethylamine / chloroform / 5 h / 50 °C

8: triethylamine / tetrahydrofuran / 8 h / Reflux

With sodium tetrahydroborate; N-Bromosuccinimide; thionyl chloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; chloroform;

upstream raw materials:

methyl 5-bromo-8-p-toluenesulfonyloxy-1,6-naphthyridine-7-carboxylate

trans-N-Boc-1,4-cyclohexanediamine

5-bromo-8-hydroxy-[1,6]naphthyridine-7-carboxylic acid methyl ester

3-hydroxymethyl-pyridine-2-carboxylic acid isopropyl ester

Downstream raw materials:

5-bromo-8-(((1r,4r)-4-((tert-butoxycarbonyl)amino)cyclohexyl)amino)-1,6-naphthyridine-7-carboxylic acid

tert-butyl ((1r,4r)-4-(5-bromo-2-oxo-2,3-dihydro-1h-imidazo[4,5-h][1,6]naphthyridin-1-yl)cyclohexyl)carbamate

C₂₇H₃₀BrN₅O₅S

C₂₇H₂₉Cl₂N₅O₄

Refernces

• 1、 Wang, Yong,Xu, Zhong-Liang,Ai, Jing,Peng, Xia,Lin, Jian-Ping,Ji, Yin-Chun,Geng, Mei-Yu,Long, Ya-Qiu. "Investigation on the 1,6-naphthyridine motif: Discovery and SAR study of 1H-imidazo[4,5-h][1,6]naphthyridin-2(3H)-one-based c-Met kinase inhibitors". . p. 1545 - 1562. Retrieved 2013/05/09.