N₄-(3-chloro-4-fluorophenyl)-7-(2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethoxy)quinazolin-4,6-diamine

Base Information

• Chemical Name: N₄-(3-chloro-4-fluorophenyl)-7-(2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethoxy)quinazolin-4,6-diamine
• CAS No.: 1363359-70-9
• Molecular Formula: C₂₂H₂₃ClFN₅O
• Molecular Weight: 427.909

Synonyms:N₄-(3-chloro-4-fluorophenyl)-7-(2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethoxy)quinazolin-4,6-diamine

Chemical Property of N₄-(3-chloro-4-fluorophenyl)-7-(2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethoxy)quinazolin-4,6-diamine

Chemical Property:

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Technology Process of N₄-(3-chloro-4-fluorophenyl)-7-(2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethoxy)quinazolin-4,6-diamine

There total 7 articles about N₄-(3-chloro-4-fluorophenyl)-7-(2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethoxy)quinazolin-4,6-diamine 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: 43.0%

N-(3-chloro-4-fluorophenyl)-7-(2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethoxy)-6-nitroquinazolin-4-amine (1363359-69-6) → N4-(3-chloro-4-fluorophenyl)-7-(2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethoxy)quinazolin-4,6-diamine (1363359-70-9)

Guidance literature:

With iron; acetic acid; In ethanol; at 20 ℃; for 12h;

Reference yield:

2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethanol (1363359-95-8) → N4-(3-chloro-4-fluorophenyl)-7-(2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethoxy)quinazolin-4,6-diamine (1363359-70-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice

1.2: 50 °C / Inert atmosphere

2.1: acetic acid; iron / ethanol / 12 h / 20 °C

With iron; sodium hydride; acetic acid; In ethanol; N,N-dimethyl-formamide;

Reference yield:

4-fluoroanthranilic acid (446-32-2) → N4-(3-chloro-4-fluorophenyl)-7-(2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethoxy)quinazolin-4,6-diamine (1363359-70-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetic acid / 2-methoxy-ethanol / Reflux

2.1: nitric acid; sulfuric acid

3.1: thionyl chloride

4.1: isopropyl alcohol

5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice

5.2: 50 °C / Inert atmosphere

6.1: acetic acid; iron / ethanol / 12 h / 20 °C

With thionyl chloride; sulfuric acid; nitric acid; iron; sodium hydride; acetic acid; In ethanol; 2-methoxy-ethanol; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethanol

N-(3-chloro-4-fluorophenyl)-7-(2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethoxy)-6-nitroquinazolin-4-amine

4-fluoroanthranilic acid

7-fluoro-3H-quinazolin-4-one

Downstream raw materials:

N-[4-(3-chloro-4-fluorophenylamino)-7-(2-((1R,5S,6S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl)ethoxy)quinazolin-6-yl]acrylamide

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