N'-(4-(7-(((5R)-4-oxaspiro[2.4]heptane-5-yl)methoxy)quinolin-4-yloxy)-3-fluorophenyl)-N-phenylcyclopropane-1,1-dicarboxamide

Base Information

• Chemical Name: N'-(4-(7-(((5R)-4-oxaspiro[2.4]heptane-5-yl)methoxy)quinolin-4-yloxy)-3-fluorophenyl)-N-phenylcyclopropane-1,1-dicarboxamide
• CAS No.: 1221443-03-3
• Molecular Formula: C₃₃H₃₀FN₃O₅
• Molecular Weight: 567.617
• Mol file: 1221443-03-3.mol

Synonyms:N'-(4-(7-(((5R)-4-oxaspiro[2.4]heptane-5-yl)methoxy)quinolin-4-yloxy)-3-fluorophenyl)-N-phenylcyclopropane-1,1-dicarboxamide

Chemical Property of N'-(4-(7-(((5R)-4-oxaspiro[2.4]heptane-5-yl)methoxy)quinolin-4-yloxy)-3-fluorophenyl)-N-phenylcyclopropane-1,1-dicarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N'-(4-(7-(((5R)-4-oxaspiro[2.4]heptane-5-yl)methoxy)quinolin-4-yloxy)-3-fluorophenyl)-N-phenylcyclopropane-1,1-dicarboxamide

There total 12 articles about N'-(4-(7-(((5R)-4-oxaspiro[2.4]heptane-5-yl)methoxy)quinolin-4-yloxy)-3-fluorophenyl)-N-phenylcyclopropane-1,1-dicarboxamide 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: 63.0%

((5R)-4-oxaspiro[2.4]heptane-5-yl)methyl methanesulfonate (1221443-22-6) + N'-(3-fluoro-4-(7-hydroxyquinolin-4-yloxy)phenyl)-N-phenylcyclopropane-1,1-dicarboxamide (1221443-50-0) → N'-(4-(7-(((5R)-4-oxaspiro[2.4]heptane-5-yl)methoxy)quinolin-4-yloxy)-3-fluorophenyl)-N-phenylcyclopropane-1,1-dicarboxamide (1221443-03-3)

Guidance literature:

With caesium carbonate; In N,N-dimethyl acetamide; at 20 - 40 ℃; for 44h; Inert atmosphere;

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → N'-(4-(7-(((5R)-4-oxaspiro[2.4]heptane-5-yl)methoxy)quinolin-4-yloxy)-3-fluorophenyl)-N-phenylcyclopropane-1,1-dicarboxamide (1221443-03-3)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridinium p-toluenesulfonate / dichloromethane / 20 °C / Inert atmosphere

2: titanium(IV) isopropylate / tetrahydrofuran; diethyl ether / 4 h / 15 °C / Inert atmosphere

3: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere

4: methanol; pyridinium p-toluenesulfonate / 20 - 40 °C / Inert atmosphere

5: triethylamine / dichloromethane / -10 - 20 °C / Inert atmosphere

6: caesium carbonate / N,N-dimethyl acetamide / 44 h / 20 - 40 °C / Inert atmosphere

With titanium(IV) isopropylate; methanol; pyridinium p-toluenesulfonate; caesium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl acetamide;

Reference yield:

ethyl (phenylcarbamoyl)cyclopropanecarboxylate (113117-83-2) → N'-(4-(7-(((5R)-4-oxaspiro[2.4]heptane-5-yl)methoxy)quinolin-4-yloxy)-3-fluorophenyl)-N-phenylcyclopropane-1,1-dicarboxamide (1221443-03-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: water; potassium hydroxide / tetrahydrofuran; ethanol / 20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: HATU / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

2.2: 24 h / 40 °C / Inert atmosphere

3.1: hydrogen / palladium on activated charcoal / methanol / 1.5 h / 20 °C

4.1: caesium carbonate / N,N-dimethyl acetamide / 44 h / 20 - 40 °C / Inert atmosphere

With water; hydrogen; caesium carbonate; HATU; potassium hydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl acetamide;

upstream raw materials:

((5R)-4-oxaspiro[2.4]heptane-5-yl)methyl methanesulfonate

N'-(3-fluoro-4-(7-hydroxyquinolin-4-yloxy)phenyl)-N-phenylcyclopropane-1,1-dicarboxamide

1-(phenylcarbamoyl)cyclopropane-1-carboxylic acid

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid