Category: 13544-06-4

Geuns-Meyer, Stephanie D. et al. published their patent in 2005 |CAS: 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

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

Mattson, Ronald et al. published their patent in 2002 |CAS: 13544-06-4

The Article related to cyclopropylindole preparation selective serotonin reuptake inhibitor, indole cyclopropyl preparation selective serotonin reuptake inhibitor, depression anxiety premature ejaculation obsessive compulsive disorder treatment cyclopropylindole, feeding disorder premenstrual dysphoric disorder panic disorder treatment cyclopropylindole and other aspects.Reference of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile

On October 10, 2002, Mattson, Ronald; Denhart, Derek; Deskus, Jeffrey; Ditta, Jonathan; Marcin, Lawrence; Epperson, James; Catt, John; King, Dalton; Higgins, Mendi published a patent.Reference of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile The title of the patent was Preparation of cyclopropylindoles as selective serotonin reuptake inhibitors. And the patent contained the following:

Treatment of depression, anxiety disorders, premature ejaculation, chronic pain, obsessive-compulsive disorder, feeding disorders, premenstrual dysphoric disorder, panic disorders and psychotic disorders including bipolar disorder and schizophrenia. Title compounds [I; A1, A2 = alkylene, bond; A3 = alkylene, alkylidene; A4 = alkylene, bond; X, X1, X2 X3 = C, CH; J = alkyl; p = 0, 1; R1, R2 = H, alkyl, (substituted) cycloalkyl, Ph, PhO , NHCO2alkyl, alkylNHCO2, thienyl, furanyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, pyridyl, pyrimidinyl, piperidinyl, piperazinyl, morpholino, adamantyl, indolyl, isoindolyl, indolinyl, quinolinyl, dihydroquinolinyl, tetrahydroquinolinyl, isoquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl; or A1R1 and A2R2 together with the N to which they are attached = pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, pyridyl, pyrimidinyl, piperidinyl, piperazinyl, morpholino, adamantyl, indolyl, isoindolyl, indolinyl, quinolinyl, dihydroquinolinyl, tetrahydroquinolinyl, isoquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl and are optionally substituted with halo, alkyl, alkoxy, cyano, benzyl; R3 = H, alkyl; m = 0, 1; R4, R5 = H, cyano, halo, NO2, perfluoroalkyl; n = 0, 1; G = N, O, S; G1 = N, CH; Y = DH; D = C; Z = EH; E = C; with provisos], were prepared for treatment of depression, anxiety, premature ejaculation, chronic pain, obsessive-compulsive disorder, feeding disorders, premenstrual dysphoric disorder, panic disorder, and psychotic disorders including bipolar disorder and schizophrenia. Thus, a solution of di-Et (N-methoxy-N-methylcarbamoylmethyl)phosphonate in THF was added to a stirred suspension of sodium hydride in THF at 0°; the reaction was warmed to room temperature and was stirred for 2 h; After cooling to 0°, [5-cyano-1-(p-toluenesulfonyl)indol-3-yl]carboxaldehyde (preparation given) was added. The resulting mixture was stirred at 0° for 1 h to give 91% (E)-[5-cyano-1-(p-toluenesulfonyl)indol-3-yl]-N-methoxy-N-methylacrylamide. This was converted to trans-2-(5-cyanoindol-3-yl)-1-(N,N-dimethylaminomethyl)cyclopropane in several steps. The latter showed serotonin transporter binding with Ki<1 nM. The experimental process involved the reaction of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile(cas: 13544-06-4).Reference of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile

The Article related to cyclopropylindole preparation selective serotonin reuptake inhibitor, indole cyclopropyl preparation selective serotonin reuptake inhibitor, depression anxiety premature ejaculation obsessive compulsive disorder treatment cyclopropylindole, feeding disorder premenstrual dysphoric disorder panic disorder treatment cyclopropylindole and other aspects.Reference of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

9/18/2021 News Introduction of a new synthetic route about 13544-06-4

According to the analysis of related databases, 13544-06-4, the application of this compound in the production field has become more and more popular.

Reference of 13544-06-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 13544-06-4 as follows.

Step 1. Preparation of 2-Methyl-2-(2-nitro-4- trifluoromethyl-phenyl) -propionitrile; The title compound was synthesized according to a method described in Prasad, G. , J. Org. Chem. 1991,56, 7188-7190. To a yellow-brown solution of (2-Nitro-4-trifluoromethyl- phenyl) -acetonitrile (2.5 g, 11 mmol), 18-crown-6 (0.72 g, 2.7 mmol), and methyl iodide (1.5 mL, 24 mmol) in dry THF under nitrogen at-78 degrees C was added potassium tert- butoxide (2.7 g, 24 mmol) in one portion. The reaction immediately became a deep purple color. The reaction was allowed to stir for 2 h at-78 degrees C, and was then warmed to ambient temperature. A water-cooled reflux condenser was added and the solution heated to 70 degrees C under nitrogen. Over 40 minutes, the color changed from dark purple to cloudy gray. The mixture was allowed to cool to room temperature, and was concentrated in vacuo. The resulting material was partitioned between 1 N HCI and EtOAc. The organic layer was washed once with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown oil which was judged to be primarily monoalkylated nitrile. The crude material was resubjected to the reaction conditions using 18-crown-6 (0.72 mg, 2.7 mmol), methyl iodide (0.75 mL, 12 mmol), and potassium tert- butoxide (1.4 g, 12 mmol) as before, with the following modifications: the reaction was allowed to stir only 10 min. at-78 degrees C before being warmed to room temperature, and the reaction vessel was sealed and heated to 70 degrees C for 2 h. Upon cooling to room temperature, the reaction was quenched and worked up as before. Purification by flash chromatography afforded the desired product as a light brown solid. MS (M+H) + = 259; Calc’d 258.20 for C11H9F3N2O2.

According to the analysis of related databases, 13544-06-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2005/113494; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Introduction of a new synthetic route about C9H5F3N2O2

According to the analysis of related databases, 13544-06-4, the application of this compound in the production field has become more and more popular.

Application of 13544-06-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 13544-06-4 as follows.

Step 1. Preparation of 2-Methyl-2-(2-nitro-4- trifluoromethyl-phenyl) -propionitrile; The title compound was synthesized according to a method described in Prasad, G. , J. Org. Chem. 1991,56, 7188-7190. To a yellow-brown solution of (2-Nitro-4-trifluoromethyl- phenyl) -acetonitrile (2.5 g, 11 mmol), 18-crown-6 (0.72 g, 2.7 mmol), and methyl iodide (1.5 mL, 24 mmol) in dry THF under nitrogen at-78 degrees C was added potassium tert- butoxide (2.7 g, 24 mmol) in one portion. The reaction immediately became a deep purple color. The reaction was allowed to stir for 2 h at-78 degrees C, and was then warmed to ambient temperature. A water-cooled reflux condenser was added and the solution heated to 70 degrees C under nitrogen. Over 40 minutes, the color changed from dark purple to cloudy gray. The mixture was allowed to cool to room temperature, and was concentrated in vacuo. The resulting material was partitioned between 1 N HCI and EtOAc. The organic layer was washed once with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown oil which was judged to be primarily monoalkylated nitrile. The crude material was resubjected to the reaction conditions using 18-crown-6 (0.72 mg, 2.7 mmol), methyl iodide (0.75 mL, 12 mmol), and potassium tert- butoxide (1.4 g, 12 mmol) as before, with the following modifications: the reaction was allowed to stir only 10 min. at-78 degrees C before being warmed to room temperature, and the reaction vessel was sealed and heated to 70 degrees C for 2 h. Upon cooling to room temperature, the reaction was quenched and worked up as before. Purification by flash chromatography afforded the desired product as a light brown solid. MS (M+H) + = 259; Calc’d 258.20 for C11H9F3N2O2.

According to the analysis of related databases, 13544-06-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2005/113494; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Sources of common compounds: 13544-06-4

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile, its application will become more common.

Related Products of 13544-06-4,Some common heterocyclic compound, 13544-06-4, name is 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile, molecular formula is C9H5F3N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

1.75 g (7.6 mmol) (2-Nitro-4-trifluoromethylphenyl)-acetonitrile in 20 ml THF are cooled to 0C in a nitrogen atmosphere and treated with 60 mi BH3/THF- complex (1 M in THF). The reaction mixture is allowed to slowly warm up to room temperature overnight. After 72 h the reaction solution is slowly given to 50 ml 5 N HO gegeben and then 1 h heated to reflux. The reaction mixture is evaporated to dryness, the residue made alkaline (pH 12-14) with 25% NaOH solution and extracted 2x with 100 mi ethylacetate. The combined organic phases are washed with brine, dried using Na2SO4, filtered and evaporated. Yield : 1.8 g (77 %) 112, brown oil

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; WO2005/75425; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Extracurricular laboratory: Synthetic route of 13544-06-4

The synthetic route of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Related Products of 13544-06-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 13544-06-4, name is 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 155 Methyl-[2-(6-trifluoromethyl-1H-indol-3-yl)-cyclopropylmethyl]-amine The commercially available (2-nitro-4-trifluoromethylphenyl) acetonitrile (14.0 g, 60.8 mmol) was dissolved in 9:1 EtOH:H2O (50 mL) and glacial acetic acid (1.4 mL). This mixture was hydrogenated over 10% Pd/C (5.0 g) at 50 psi for 16 h at room temperature. The reaction was filtered over celite and evaporated in vacuo. The residue was partitioned between saturated aqueous sodium carbonate and dichloromethane (2*200 mL) and the combined organic extract was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by silica gel column chromatography (hexanes/ethyl acetate, 20:1, 9:1, 5:1) to afford 12.9 g (65% yield) of 6-trifluoromethyl-1H-indole as a yellow solid: 1H NMR (400 MHz, CDCl3) 8.36, (1H, br s), 7.72 (2 H, m), 7.37 (2 H, m), 6.63 (1 H, m); MS m/e 184 (M-H)-. Anal calcd. for C9H6F3N: C, 58.38; H, 3.26; N, 7.56. Found: C, 58.30; H, 2.92; N, 7.49.

The synthetic route of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mattson, Ronald J.; Denhart, Derek John; Deskus, Jeffrey A.; Ditta, Jonathan L.; Marcin, Lawrence R.; Epperson, James R.; Catt, John D.; King, Dalton; Higgins, Mendi A.; US2003/73849; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts