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

Base Information

• Chemical Name: tert-butyl ((1r,4r)-4-(5-bromo-2-oxo-2,3-dihydro-1h-imidazo[4,5-h][1,6]naphthyridin-1-yl)cyclohexyl)carbamate
• CAS No.: 1422434-40-9
• Molecular Formula: C₂₀H₂₄BrN₅O₃
• Molecular Weight: 462.346

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

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

Chemical Property:

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

There total 2 articles about tert-butyl ((1r,4r)-4-(5-bromo-2-oxo-2,3-dihydro-1h-imidazo[4,5-h][1,6]naphthyridin-1-yl)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: 83.0%

5-bromo-8-(((1r,4r)-4-((tert-butoxycarbonyl)amino)cyclohexyl)amino)-1,6-naphthyridine-7-carboxylic acid (1223081-81-9) → tert-butyl ((1r,4r)-4-(5-bromo-2-oxo-2,3-dihydro-1h-imidazo[4,5-h][1,6]naphthyridin-1-yl)cyclohexyl)carbamate (1422434-40-9)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; In toluene; for 8h; Reflux;

Reference yield:

tert-butyl(1r,4r)-4-(7-(methoxycarbonyl)-5-bromo-1,6-naphthyridin-8-amino)cyclohexyl carbamate (1223081-79-5) → tert-butyl ((1r,4r)-4-(5-bromo-2-oxo-2,3-dihydro-1h-imidazo[4,5-h][1,6]naphthyridin-1-yl)cyclohexyl)carbamate (1422434-40-9)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium hydroxide; water / tetrahydrofuran / 20 °C / Inert atmosphere

2: diphenyl phosphoryl azide; triethylamine / toluene / 90 °C

With diphenyl phosphoryl azide; water; triethylamine; lithium hydroxide; In tetrahydrofuran; toluene;

DOI:10.1039/c2ob26710a

Reference yield: 90.9%

tert-butyl ((1r,4r)-4-(5-bromo-2-oxo-2,3-dihydro-1h-imidazo[4,5-h][1,6]naphthyridin-1-yl)cyclohexyl)carbamate (1422434-40-9) + 3,4-dichlorobenzyl bromide (18880-04-1) → C27H28BrCl2N5O3 (1422434-00-1)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1039/c2ob26710a

upstream raw materials:

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

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

Downstream raw materials:

C₂₇H₂₉Cl₂N₅O₄

C₃₂H₃₂Cl₂N₆O₄

C₃₄H₃₃Cl₂N₅O₅

C₃₄H₃₂Cl₃N₅O₅

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