On December 1, 2005, Geuns-Meyer, Stephanie D.; Hodous, Brian L.; Chaffee, Stuart C.; Tempest, Paul A.; Olivieri, Philip R.; Johnson, Rebecca E.; Albrecht, Brian K.; Patel, Vinod F.; Cee, Victor J.; Kim, Joseph L.; Bellon, Steven; Zhu, Xiaotian; Cheng, Yuan; Xi, Ning; Romero, Karina; Nguyen, Hanh Nho; Deak, Holly L. published a patent.Synthetic Route of 13544-06-4 The title of the patent was Preparation of nitrogen-heteroaryl-containing protein kinase modulators for use against cancer and other diseases. And the patent contained the following:
The present invention relates to nitrogen-heteroaryl-containing compounds (shown as I; variables defined below; e.g. 4-fluoro-3-[[3-(pyrimidin-4-yl)pyridin-2-yl]amino]-N-[3-[(tetrahydrofuran-2-yl)methoxy]-5-trifluoromethylphenyl]benzamide (shown as II)) and synthetic intermediates, which are capable of modulating various protein kinase receptor enzymes and, thereby, influencing various disease states and conditions related to the activities of these kinases. For example, the compounds are capable of modulating kinase enzymes thereby influencing the process of angiogenesis and treating angiogenesis-related diseases and other proliferative disorders, including cancer and inflammation. The invention also includes pharmaceutical compositions, including the compounds, and methods of treating disease states related to the activity of protein kinases. For I: A is N or CR10; B is N or CR11; D is N or CR12; E is N or CH; G is NR13, O, S, C(O), S(O), SO2, CR13R13 or CR13R14; H1 is N or CR5; H2 is N or CR6; H3 is N or CR7; H4 is N or CR5; H5 is N or CR9; R1 is H, halo, haloalkyl, NO2, CN, NR13R13, OR13, SR13 (CHR13)nR13, or R15; alternatively R1 taken together with R10 forms a partially or fully unsaturated 5- or 6-membered ring of C atoms optionally including 1-3 heteroatoms = O, N and S, and the ring (un)substituted; R2 is H, halo, haloalkyl, oxo, NO2, CN, SR13, et al.; each of R3 and R4, independently, is H, halo, haloalkyl, oxo, NO2, CN, SR13, et al.; addnl. details including provisos are given in the claims. Although the methods of preparation are not claimed, preparations and/or characterization data for >1200 examples of I and intermediates are included. For example, II was prepared in 2 steps starting with condensation of 4-(2-chloropyridin-3-yl)pyrimidine (preparation given) with 3-amino-4-fluorobenzoic acid in Et3N-TFA to give 4-fluoro-3-[[3-(pyrimidin-4-yl)pyridin-2-yl]amino]benzoic acid, which was condensed with [3-[(tetrahydrofuran-2-yl)methoxy]-5-trifluoromethylphenyl]amine using EDC and DMAP in DMF. The experimental process involved the reaction of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile(cas: 13544-06-4).Synthetic Route of 13544-06-4
The Article related to nitrogen heteroaryl containing protein kinase modulator antitumor antiinflammatory, aurora kinase modulator nitrogen heteroaromatic compound preparation, cmet tyrosine kinase modulator nitrogen heteroaromatic compound preparation, braf kinase modulator nitrogen heteroaromatic compound preparation and other aspects.Synthetic Route of 13544-06-4
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts