Tag: 200-300

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

On December 1, 2009, Ioannidis, Stephanos; Lamb, Michelle L.; Davies, Audrey M.; Almeida, Lynsie; Su, Mei; Bebernitz, Geraldine; Ye, Minwei; Bell, Kirsten; Alimzhanov, Marat; Zinda, Michael published an article.HPLC of Formula: 5098-14-6 The title of the article was Discovery of pyrazol-3-ylamino pyrazines as novel JAK2 inhibitors. And the article contained the following:

Pyridineethyl- and pyrimidineethyl-substituted pyrazoleaminopyrazines such as I (R = Me; X = N) and I (R = H; X = CH) are prepared as selective JAK2 kinase inhibitors for potential use as anticancer agents; the GI50 values for their JAK2 and JAK3 kinase inhibition are determined The activities of selected pyridineethyl- and pyrimidineethyl-substituted pyrazoleaminopyrazines in a functional phosphorylation model in mice and their inhibition of aurora B kinase, cyclin-dependent kinase 2, and TrkA are determined; the pharmacokinetics and pharmacodynamics of I (R = Me; X = N) and of I (R = H; X = CH) in rats and beagles are also determined The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).HPLC of Formula: 5098-14-6

The Article related to pyridineethyl pyrimidineethyl pyrazoleaminopyrazine preparation selective jak2 kinase inhibitor, structure pyridineethyl pyrimidineethyl pyrazoleaminopyrazine jak2 kinase inhibition selectivity, pharmacokinetics pharmacodynamics pyrimidineethyl pyrazoleaminopyrazine jak2 kinase inhibitor and other aspects.HPLC of Formula: 5098-14-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Saa, Carlos; Crotts, Dallas D.; Hsu, Gishun; Vollhardt, K. Peter C. published an article in Synlett. The title of the article was 《A cobalt-catalyzed entry into the ergot alkaloids: total syntheses of (±)-lysergene and (±)-LSD》.Computed Properties of C10H7BrN2 The author mentioned the following in the article:

Cocyclization of 4-ethynyl-3-indoleacetonitriles with alkynes in the presence of CpCo(CO)2 gives rise to the ergoline derivatives e.g. I (R = CH2OH, CONEt2), which were transformed into racemic lysergene (II) and LSD, resp. The experimental process involved the reaction of 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Computed Properties of C10H7BrN2)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Computed Properties of C10H7BrN2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of C7H3BrFNIn 2021 ,《Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates and Imines via Nickelaelectrocatalysis》 was published in JACS Au. The article was written by Zhu, Chen; Kale, Ajit Prabhakar; Yue, Huifeng; Rueping, Magnus. The article contains the following contents:

A nickel-catalyzed cross-coupling amination of aryl halides/aryl tosylates with weak nitrogen nucleophiles including anilines, sulfonamides, sulfoximines, carbamates and imines via concerted paired electrolysis was described to provide substituted amines Ar1NHAr2 [Ar1 = 4-MeC6H4, 4-NCC6H4, 4-tBuC6H4, etc.; Ar2 = Ph, 2-naphthyl, 4-MeC6H4, etc.] and aryl sulfonamides Ar3NRSO2R1 [Ar3 = 2-MeC6H4, 4-NCC6H4, 4-tBuC6H4, etc.; R = H, Me R1 = Me, Bn, 4-MeC6H4, etc.]. Notably, electron-deficient anilines and sulfonamides were also suitable substrates. Interestingly, when benzophenone imine was applied in the arylation, the product selectivity toward the formation of amine and imine product could be addressed by a base switch. In addition, the a.c. mode could be successfully applied. DFT calculations supported a facilitated reductive elimination pathway. In the experiment, the researchers used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Synthetic Route of C7H3BrFN)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Synthetic Route of C7H3BrFN It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Name: 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrileOn May 31, 2022, Yang, Hongchen; Zhang, Lu; Xu, Xiaoyong; Shao, Xusheng; Li, Zhong published an article in Synlett. The article was 《Acid-Mediated Synthesis of Chromeno[2,3-b]pyridine Derivatives via Condensation of 2-Amino-3-formylchromones and 1-(Methylthio)-2-nitroenamine Derivatives》. The article mentions the following:

A convenient and effective protocol has been proposed for the synthesis of chromeno[2,3-b]pyridines I (R1 = H, i-Pr; R2 = Me, Et, PhCH2, etc.) via the CF3SO3H-catalyzed annulation of substituted 2-amino-3-formylchromones II and various 1-(methylthio)-2-nitroenamines R2NHC(SMe):CHNO2. This method is time-efficient, convenient, high-yielding and exhibits a good functional group compatibility. In addition to this study using 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile, there are many other studies that have used 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile(cas: 50743-32-3Name: 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile) was used in this study.

6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile(cas: 50743-32-3) belongs to nitriles. Nitriles are found in many useful compounds. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.Name: 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Groth, Ulrich; Huhn, Thomas; Kesenheimer, Christian; Kalogerakis, Aris published an article in Synlett. The title of the article was 《Cobalt-mediated regioselective synthesis of substituted tetrahydroquinolines》.Application In Synthesis of 2-(4-Bromo-3-indolyl)acetonitrile The author mentioned the following in the article:

A regioselective synthesis of polycyclic substituted pyridines, e.g., I, is reported. Key step was the cobalt-catalyzed intramol. cyclization of diynenitriles, tethered by a silicon oxygen bond. Subsequent opening of the Si-O ring led then to the related tetrahydroquinolines. The results came from multiple reactions, including the reaction of 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Application In Synthesis of 2-(4-Bromo-3-indolyl)acetonitrile)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Application In Synthesis of 2-(4-Bromo-3-indolyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Synthesis of PI3K inhibitor GDC-0077 via a stereocontrolled N-arylation of α-amino acids》 were Han, Chong; Kelly, Sean M.; Cravillion, Theresa; Savage, Scott J.; Nguyen, Tina; Gosselin, Francis. And the article was published in Tetrahedron in 2019. Category: nitriles-buliding-blocks The author mentioned the following in the article:

An efficient synthesis of PI3K inhibitor GDC-0077, featuring two consecutive Cu-catalyzed C-N coupling reactions, is reported. The described synthetic route involves a chemoselective Ullmann-type coupling of a chiral difluoromethyl-substituted oxazolidinone, a Cu-catalyzed N-arylation of L-alanine with high stereochem. integrity, and a high-yielding final amide bond formation step to produce GDC-0077 in >99.5 area % HPLC purity. In the experiment, the researchers used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Category: nitriles-buliding-blocks)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Category: nitriles-buliding-blocks It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Palladium Nanoparticles Immobilized on Schiff Base-Functionalized Graphene-Oxide: Application in Carbon-Carbon Cross-Coupling Reactions》 were Parmanand; Kumari, Shweta; Mittal, Ayushi; Kumar, Anoop; Krishna; Sharma, Sunil K.. And the article was published in ChemistrySelect in 2019. Reference of 4-Bromo-2-fluorobenzonitrile The author mentioned the following in the article:

Palladium nanoparticles immobilized on Schiff base-functionalized graphene-oxide (GO-Pd) was synthesized and characterized by FT-IR, Raman, PXRD, UV-Visible, TGA, XPS, FE-SEM, TEM, EDAX, Elemental mapping, BET, AAS and ICP MS anal. The GO-Pd showed promising catalytic activity for the Suzuki-Miyaura, Hiyama and Heck-Mizoroki coupling reactions with higher yields (up to 95%). The GO-Pd could be easily filtered out from the reaction mixture and reused up to six times without significant loss of catalytic activity. All of the synthetic products obtained were fully characterized from their spectral data. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Reference of 4-Bromo-2-fluorobenzonitrile)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Reference of 4-Bromo-2-fluorobenzonitrile It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liu, Wei; Buck, Matthew; Chen, Nan; Shang, Muhong; Taylor, Nicholas J.; Asoud, Jalil; Wu, Xing; Hasinoff, Brian B.; Dmitrienko, Gary I. published an article in Organic Letters. The title of the article was 《Total Synthesis of Isoprekinamycin: Structural Evidence for Enhanced Diazonium Ion Character and Growth Inhibitory Activity toward Cancer Cells》.Product Details of 325141-71-7 The author mentioned the following in the article:

The structurally novel diazobenzo[a]fluorene antibiotic isoprekinamycin (IPK, I) has been synthesized for the first time employing a Suzuki coupling of a brominated AB ring synthon with a boronate ester representing the D ring, followed by anionic cyclization and appropriate functional group manipulations. The first indication that the diazobenzo[a]fluorene system exhibits in vitro anticancer activity is provided and X-ray crystallog. evidence for enhancement of diazonium ion character as a consequence of intramol. H-bonding is described.2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile(cas: 325141-71-7Product Details of 325141-71-7) was used in this study.

2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile(cas: 325141-71-7) belongs to nitriles. Nitriles are found in many useful compounds. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Product Details of 325141-71-7 Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Regioregularity and Electron Deficiency Control of Unsymmetric Diketopyrrolopyrrole Copolymers for Organic Photovoltaics》 were Aoshima, Kenta; Nomura, Mayuka; Saeki, Akinori. And the article was published in ACS Omega in 2019. Formula: C7H3BrFN The author mentioned the following in the article:

Manipulating the electron deficiency and controlling the regioregularity of π-conjugated polymers are important for the fine-tuning of their electronic and electrochem. properties to make them suitable for an organic solar cell. Here, we report such a mol. design of unsym. diketopyrrolopyrrole (DPP) based copolymers with different aromatic side units of either thiophene (Th), pyridine (Py), or fluorobenzene (FBz). The unsym. electron acceptors of Th-DPP-Py and Th-DPP-FBz were polymerized with the electron donor of two-dimensional benzobisthiophene (BDT-Th), affording two regiorandom DPP copolymers. They exhibited contrasting MO levels and bulk heterojunction morphol. in methanofullerene-blended films, leading to power conversion efficiencies of 3.75 and 0.18%, resp. We further synthesized a regioregular DPP copolymer via sandwiching the centrosym. BDT-Th unit by two Th-DPP-Py units in an axisym. manner. The extensive characterization through morphol. observation, X-ray diffraction, and space-charge-limited current mobilities highlight the case-dependent pos./neg. effects of regioregularity and electron deficiency control. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Formula: C7H3BrFN)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Formula: C7H3BrFN It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts