N-(3-{2-[3-Fluoro-4-(4-methyl-piperazin-1-yl)-phenylamino]-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy}-phenyl)-acrylamide

Base Information

• Chemical Name: N-(3-{2-[3-Fluoro-4-(4-methyl-piperazin-1-yl)-phenylamino]-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy}-phenyl)-acrylamide
• CAS No.: 1557267-42-1
• Molecular Formula: C26H26FN7O2
• Molecular Weight: 487.537
• Mol file: 1557267-42-1.mol

Synonyms:N-(3-{2-[3-Fluoro-4-(4-methyl-piperazin-1-yl)-phenylamino]-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy}-phenyl)-acrylamide;Avi Tini;Avitinib;2-Propenamide, N-[3-[[2-[[3-fluoro-4-(4-methyl-1-piperazinyl)phenyl]amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]-

Chemical Property of N-(3-{2-[3-Fluoro-4-(4-methyl-piperazin-1-yl)-phenylamino]-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy}-phenyl)-acrylamide

Chemical Property:

• PKA: 12.48±0.50(Predicted)
• PSA: 98.41000
• Density: 1.365±0.06 g/cm3(Predicted)
• LogP: 4.65810

Purity/Quality:

99%min ^*data from raw suppliers

Avitinibfreebase >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Avitinib is a pyrrolopyrimidine-based, irreversible inhibitor of the epidermal growth factor receptor (EGFR). It is selective for EGFR-active and T790M mutations, exhibiting a 298-fold increase in potency compared with wild-type EGFR. In a xenograft model, oral administration of 500 mg/kg avitinib was shown to result in complete remission of tumors with EGFR-active and T790M mutations.

Technology Process of N-(3-{2-[3-Fluoro-4-(4-methyl-piperazin-1-yl)-phenylamino]-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy}-phenyl)-acrylamide

There total 19 articles about N-(3-{2-[3-Fluoro-4-(4-methyl-piperazin-1-yl)-phenylamino]-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy}-phenyl)-acrylamide 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: 92.09%

4-(3-aminophenoxy)-N-(3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-2-amine + acryloyl chloride (814-68-6,25189-84-8) → N-(3-((2-((3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)amino)-7H-pyrrolo(2,3-d)pyrimidin-4-yl)oxy)phenyl)prop-2-enamide (1557267-42-1)

Guidance literature:

4-(3-aminophenoxy)-N-(3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-2-amine; With potassium carbonate; In tetrahydrofuran; water; at 10 ℃; for 1h;

acryloyl chloride; In tetrahydrofuran; water; at 10 ℃; for 1h; Reagent/catalyst; Temperature; Solvent;

Reference yield: 86.7%

N-(3-(2-(3-fluoro-4-(4-methylpiperazin-1-yl)phenylamino)-7-(hydroxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl)acrylamide (1557267-50-1) → N-(3-((2-((3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)amino)-7H-pyrrolo(2,3-d)pyrimidin-4-yl)oxy)phenyl)prop-2-enamide (1557267-42-1)

Guidance literature:

With ethanol; potassium carbonate; at 20 ℃; for 4h;

Reference yield: 83.0%

→ N-(3-((2-((3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)amino)-7H-pyrrolo(2,3-d)pyrimidin-4-yl)oxy)phenyl)prop-2-enamide (1557267-42-1)

Guidance literature:

With ammonia; In methanol; at 20 ℃;

upstream raw materials:

acryloyl chloride

2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine

pivalic acid (2-chloro-4-(3-nitrophenoxy)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl ester

1-(2-fluoro-4-aminophenyl)-4-methylpiperazine

Downstream raw materials:

N-(3-(2-(3-fluoro-4-(4-methylpiperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl)acrylamide maleate

N-(3-(2-(3-fluoro-4-(4-methylpiperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl)acrylamide maleate

N-(3-(2-(3-fluoro-4-(4-methylpiperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl)acrylamide fumarate

C₄H₄O₄*C₂₆H₂₆FN₇O₂

Refernces

• 1、 -. "Pyrrolo [2, 3-d] pyrimidine derivative targeting EGFR mutation as well as preparation method and application of pyrrolo [2, 3-d] pyrimidine derivative". . . Retrieved 2020/11/10.
• 2、 -. "Preparing method of Avitinib". Paragraph 0019-0021; 0027-0042; 0045. . Retrieved 2019/11/14.