Benzamide, N-[3-[1,4-dihydro-1-methyl-7-[(6-methyl-3-pyridinyl)amino]-2-oxopyrimido[4,5-d]pyrimidin-3(2H)-yl]-4-methylphenyl]-3-(trifluoromethyl)-

Base Information

• Chemical Name: Benzamide, N-[3-[1,4-dihydro-1-methyl-7-[(6-methyl-3-pyridinyl)amino]-2-oxopyrimido[4,5-d]pyrimidin-3(2H)-yl]-4-methylphenyl]-3-(trifluoromethyl)-
• CAS No.: 839706-07-9
• Molecular Formula: C28H24F3N7O2
• Molecular Weight: 547.53
• Mol file: 839706-07-9.mol

Synonyms:2H-1,4-Benzothiazine,urea deriv.;

Chemical Property of Benzamide, N-[3-[1,4-dihydro-1-methyl-7-[(6-methyl-3-pyridinyl)amino]-2-oxopyrimido[4,5-d]pyrimidin-3(2H)-yl]-4-methylphenyl]-3-(trifluoromethyl)-

Chemical Property:

• PKA: 12.82±0.70(Predicted)
• PSA: 106.84000
• Density: 1.404±0.06 g/cm3(Predicted)
• LogP: 6.66650
• Solubility.: insoluble in EtOH; insoluble in H2O; ≥5.48 mg/mL in DMSO

Purity/Quality:

99% ^*data from raw suppliers

GNF7 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: GNF 7 inhibits ras signaling, Ack1 and germinal center kinase (GCK). Also, it suppresses proliferation, and induces cell cycle arrest and apoptosis in leukemia cells harboring NRAS mutations. It is a COVID19-related research product.

Technology Process of Benzamide, N-[3-[1,4-dihydro-1-methyl-7-[(6-methyl-3-pyridinyl)amino]-2-oxopyrimido[4,5-d]pyrimidin-3(2H)-yl]-4-methylphenyl]-3-(trifluoromethyl)-

There total 8 articles about Benzamide, N-[3-[1,4-dihydro-1-methyl-7-[(6-methyl-3-pyridinyl)amino]-2-oxopyrimido[4,5-d]pyrimidin-3(2H)-yl]-4-methylphenyl]-3-(trifluoromethyl)- 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: 81.0%

5-Amino-2-methylpyridine (80287-53-2,3430-14-6) + N-(3-(7-chloro-1-methyl-2-oxo-1,4-dihydropyrimido[4,5-d]-pyrimidin-3(2H)-yl)-4-methylphenyl)-3-(trifluoromethyl)benzamide (839708-52-0) → GNF-7 (839706-07-9)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; XPhos; In iso-butanol; at 100 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.8b00882

Reference yield: 32.0%

5-Amino-2-methylpyridine (80287-53-2,3430-14-6) + N-(4-methyl-3-(1-methyl-7-(methylsulfonyl)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)phenyl)-3-(trifluoromethyl)-benzamide (839705-68-9) → GNF-7 (839706-07-9)

Guidance literature:

With trifluoroacetic acid; In 1,4-dioxane; at 120 ℃; for 48h;

DOI:10.1021/jm901808w

Reference yield:

N-((2,4-dichloropyrimidin-5-yl)methyl)-2-methyl-5-nitroaniline → GNF-7 (839706-07-9)

Guidance literature:

Multi-step reaction with 5 steps

1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane; methanol / 1.5 h / 60 °C / Inert atmosphere

2: triethylamine / tetrahydrofuran / 1 h / 0 - 70 °C / Inert atmosphere

3: iron; ammonium chloride / methanol; tetrahydrofuran; water / 2 h / 80 °C / Inert atmosphere

4: potassium carbonate / dichloromethane / 1 h / 20 °C / Inert atmosphere

5: potassium carbonate; XPhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / iso-butanol / 1 h / 100 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; iron; potassium carbonate; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; XPhos; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; iso-butanol;

DOI:10.1021/acs.jmedchem.8b00882

upstream raw materials:

5-Amino-2-methylpyridine

N-(4-methyl-3-(1-methyl-7-(methylsulfonyl)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)phenyl)-3-(trifluoromethyl)-benzamide

5-(hydroxymethyl)pyrimidine-2,4-diol

2,4-dichloro-5-(chloromethyl)pyrimidine

Refernces

• 1、 Choi, Hwan Geun,Ren, Pingda,Adrian, Francisco,Sun, Fangxian,Lee, Hyun Soo,Wang, Xia,Ding, Qiang,Zhang, Guobao,Xie, Yongping,Zhang, Jianming,Liu, Yi,Tuntland, Tove,Warmuth, Markus,Manley, Paul W.,Mestan, Jürgen,Gray, Nathanael S.,Sim, Taebo. "A type-ii kinase inhibitor capable of inhibiting the T315I "Gatekeeper" mutant of Bcr-Abl". experimental part. p. 5439 - 5448. Retrieved 2010/11/05.