Category: nitriles-buliding-blocks

On April 13, 2017, Gopalsamy, Ariamala; Narayanan, Arjun; Liu, Shenping; Parikh, Mihir D.; Kyne, Robert E.; Fadeyi, Olugbeminiyi; Tones, Michael A.; Cherry, Jonathan J.; Nabhan, Joseph F.; LaRosa, Gregory; Petersen, Donna N.; Menard, Carol; Foley, Timothy L.; Noell, Stephen; Ren, Yong; Loria, Paula M.; Maglich-Goodwin, Jodi; Rong, Haojing; Jones, Lyn H. published an article.SDS of cas: 1261686-95-6 The title of the article was Design of Potent mRNA Decapping Scavenger Enzyme (DcpS) Inhibitors with Improved Physicochemical Properties To Investigate the Mechanism of Therapeutic Benefit in Spinal Muscular Atrophy (SMA). And the article contained the following:

The C-5 substituted 2,4-diaminoquinazoline RG3039 (compound I), a member of a chem. series that was identified and optimized using an SMN2 promoter screen, prolongs survival and improves motor function in a mouse model of spinal muscular atrophy (SMA). It is a potent inhibitor of the mRNA Decapping Scavenger Enzyme (DcpS), but the mechanism whereby DcpS inhibition leads to therapeutic benefit is unclear. Compound I is a dibasic lipophilic mol. that is predicted to accumulate in lysosomes. To understand if the in-vivo efficacy is due to DcpS inhibition or other effects resulting from the physicochem. properties of the chemotype, the authors undertook structure based mol. design to identify DcpS inhibitors with improved physicochem. properties. Herein the authors describe the design, synthesis, in-vitro pharmacol. characterization of these DcpS inhibitors along with the in-vivo mouse CNS PK profile of PF-DcpSi (compound II), one of the analogs found to be efficacious in SMA mouse model. The experimental process involved the reaction of 2-(Bromomethyl)-6-fluorobenzonitrile(cas: 1261686-95-6).SDS of cas: 1261686-95-6

The Article related to mrna dcps inhibitor spinal muscular atrophy pharmacokinetics, Pharmacology: Structure-Activity and other aspects.SDS of cas: 1261686-95-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On October 31, 2007, Abdelrazek, Fathy M.; Metz, Peter; Kataeva, Olga; Jaeger, Anne; El-Mahrouky, Sherif F. published an article.Synthetic Route of 75629-62-8 The title of the article was Synthesis and molluscicidal activity of new chromene and pyrano[2,3-c]pyrazole derivatives. And the article contained the following:

The molluscicidal activity of the synthesized title compounds towards Biomphalaria alexandrina snails, the intermediate host of Schistosoma mansoni, was investigated and most of them showed weak to moderate activity. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Synthetic Route of 75629-62-8

The Article related to chromene pyranopyrazole preparation molluscicidal sar, Pharmacology: Structure-Activity and other aspects.Synthetic Route of 75629-62-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Abdul Amin, Sk.; Adhikari, Nilanjan; Jha, Tarun; Gayen, Shovanlal published an article in 2016, the title of the article was Exploring structural requirements of unconventional Knoevenagel-type indole derivatives as anticancer agents through comparative QSAR modeling approaches.COA of Formula: C12H7N3 And the article contains the following content:

An indole ring system is considered as a versatile scaffold in the pharmaceutical field. In this article, comparative QSAR modeling (2D-QSAR, 3D-QSAR; kNN-MFA and Co-MSIA) was performed on some Knoevenagel-type cytotoxic indole derivatives to understand the structural requirements for the cytotoxic property of these compounds The 2D-QSAR model was statistically significant and imparted high predictive ability (nTrain = 30; R = 0.917; RA2=0.801; cRp2=0.757; Q2 = 0.722; nTest = 9; Rpred2=0.799). A statistically significant 3D-QSAR kNN-MFA model (both with stepwise forward and simulated annealing model selection method) as well as a 3D-QSAR Co-MSIA model was developed to identify the key chem. features associated with enhancing the cytotoxic activities of these indoles. The results suggest that the presence of bulky group in R position can cause better cytotoxic activities. Consequently, substitution with cyano group at X portion and cyano/ester/keto/sulfonyl features at Y position is favorable for the cytotoxicity. However, hydrophobic features in R’ region are unfavorable for the biol. activity. The chem. and structural features identified from the study may provide important avenues to modulate the structure of these indoles to a desirable biol. end point. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).COA of Formula: C12H7N3

The Article related to knoevenagel indole antitumor neoplasm qsar, Pharmacology: Structure-Activity and other aspects.COA of Formula: C12H7N3

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On August 31, 2004, Narsaiah, A. Venkat; Basak, A. K.; Visali, B.; Nagaiah, K. published an article.Quality Control of 2-((1H-Indol-3-yl)methylene)malononitrile The title of the article was An eco-friendly synthesis of electrophilic alkenes catalyzed by dimethylaminopyridine under solvent-free conditions. And the article contained the following:

Electrophilic olefins were synthesized in solvent-free condition using DMAP (10%mol) as catalyst in excellent yield and E-geometry. The various aldehydes which are aliphatic, aromatic, and heterocyclics under-went smoothly for Knoevenagel condensation with different active methylene compounds The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Quality Control of 2-((1H-Indol-3-yl)methylene)malononitrile

The Article related to aldehyde knoevenagel condensation active methylene compound dimethylaminopyridine catalyst, electrophilic alkene preparation green chem, Aliphatic Compounds: General and other aspects.Quality Control of 2-((1H-Indol-3-yl)methylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Day, Michael; Peters, Arnold Thornton published an article in 1967, the title of the article was Synthesis and ultraviolet spectra of nitrodiphenyl-amine disperse dyes. II. Synthesis of some substituted 2- and 4-nitrodiphenylamines.Reference of 3-Chloro-4-nitrobenzonitrile And the article contains the following content:

The synthesis of some substituted 2- and 4-nitrodiphenylamines, yellow dyes for synthetic fibers, is described. Condensation of 0.02 mole 2,5-Cl2C6H3NO2 with 0.04 mole PhNH2 in 50 ml. boiling EtOH containing 3 g. NaOAc gave 52.8% I (R = NO2, R1 = Cl, R2 = R3 = R4 = H), m. 59-60° (75% aqueous alc.). Other I were prepared similarly (R, R1, R2, R3, R4, % yield, and m.p. given): NO2, Cl, OMe, H, H, 50, 100-1°; NO2, Cl, H, OMe, H, 37, 90°; NO2, Cl, H, H, OMe, 48, 118-19°; NO2, Cl, F, H, H, 21, 113-14°; NO2, Cl, H, F, H, 40, 99-100°; NO2, Cl, H, H, F, 38, 80-1°; NO2, Cl, H, H, SO2Me, 15, 210-11°; CF3, NO2, H, H, H, 71, 63-4°; CF3, NO2, OMe, H, H, 16, 106-7°; CF3, NO2, H, OMe, H, 32, 88°; CF3, NO2, H, H, OMe, 74, 87-8°; CF3, NO2, F, H, H, 30, 60-1°; CF3, NO2, H, F, H, 57, 73-4°; CF3, NO2, H, H, F, 20, 74-5°; MeSO2, NO2, H, H, H, 82, 169-70°; Me, NO2, H, H, H, 23, 133-4°; NO2, Me, H, H, H, 79, 34-5°; NO2, OMe, H, H, H, 23, 44-5°. Fusion of 0.02 mole 3,4-Cl2C6H3NO2 (II) with 0.04 mole PhNH2 gave 31.8% I (R = Cl, R1 = NO2, R2 = R3 = R4 = H), m. 112-13°. Other I (R = Cl, R1 = NO2) were prepared similarly (R2, R3, R4, % yield, and m.p. given): OMe, H, H, 36, 108-9°; H, OMe, H, 25, 122-3°; H, H, OMe, 32, 99-100°; H, H, F, 20, 119-20°. Condensation of 0.02 mole 4,3-Cl(O2N)C6H3SO2NH2 (III) and 0.03 mole PhNH2 by fusing for 6 hrs. at 130° gave 71.8% I (R = NO2, R1 = SO2NH2, R2 = R3 = R4 = H), m. 179-80°. Other I (R = NO2, R1 = SO2NH2) were prepared similarly (R2, R3, R4, % yield, and m.p. given): Me, H, H, 84, 195-6°; H, Me, H, 85, 172-3°; H, H, Me, 90, 196-7°; OMe, H, H, 41, 225-6°; H, OMe, H, 91, 181-2°; H, H, OMe, 89, 226-7°; F, H, H, 61, 206-7°; H, F, H, 77, 195-6°; H, H, F, 80, 234-5°; Cl, H, H, 42, 202-3°; H, Cl, H, 80, 201-2°; H, H, Cl, 80, 241-2°; Br, H, H, 60, 200-1°; H, Br, H, 79, 207-8°; H, H, Br, 84, 235-6°; CF3, H, H, 40, 169-70°; H, CF3, H, 82, 210-11°; H, H, CF3, 29, 260-1°; H, H, SO2Me, 59, 253-4°. Condensation of 4.7 g. 2,5-Cl(O2N)C6H3SO2NH2 (IV) with 0.04 mole PhNH2 in 100 ml. boiling PhNO2 for 24 hrs. gave 68.4% I (R = SO2NH2, R1 = NO2, R2 = R3 = R4 = H), m. 175-6°. Other I (R = SO2NH2, R1 = NO2) were prepared similarly (R2, R3, R4, % yield, and m.p. given): OMe, H, H, 62, 205-8°; H, OMe, H, 59, 172-4°; H, H, OMe, 65, 160°; F, H, H, 60, 182-3°; H, F, H, 68, 173-4°; H, H, F, 71, 162-4°. A mixture of 25 g. 4,3-Cl(O2N)C6H3CO2H and 50 ml. SOCl2 was refluxed for 2 hrs., stripped of excess SOCl2, and treated with excess NH4OH to give 86.4% 4,3-Cl(O2N)C6H3CONH2, m. 154-5° (EtOH), which (0.02 mole) was condensed with 0.04 mole PhNH2 in EtOH containing NaOAc to give 34.4% I (R = NO2, R1 = CONH2, R2 = R3 = R4 = H), m. 194-5°. Other I were prepared similarly (R, R1, R2, R3, R4, % yield, and m.p. given): NO2, CONH2, OMe, H, H, 68, 144-5°; NO2, CONH2, H, OMe, H, 72, 170-1°; NO2, CONH2, H, H, OMe, 68, 220-1°; NO2, CONH2, F, H, H, 60, 169-71°; NO2, CONH2, H, F, H, 67, 191-2°; NO2, CONH2, H, H, F, 78, 207-8°; NO2, CONH2, H, H, SO2Me, 10, 244-5°; CONH2, NO2, H, H, H, 25, 184-5°; CONH2, NO2, OMe, H, H, 59, 215-16°; CONH2, NO2, H, OMe, H, 55, 198-9°; CONH2, NO2, H, H, OMe, 79, 216-17°; CONH2, NO2, F, H, H, 49, 184-5°; CONH2, NO2, H, F, H, 43, 233-4°; CONH2, NO2, H, H, F, 82, 231-2°; CONH2, NO2, H, H, SO2Me, 7, 207-8°. Esterification of 4,3-Cl(O2N)C6H3CO2H gave 4,3-Cl(O2N)C6H3CO2Et, m. 60-1° (EtOH), which was condensed with PhNH2 in boiling EtOH to give 92.8% I (R = NO2, R1 = CO2Et, R2 = R3 = R4 = H), m. 114-15°. Other I were prepared similarly (R, R1, R2, R3, R4, % yield, and m.p. given): NO2, CO2Et, OMe, H, H, 72, 116-18°; NO2, CO2Et, H, OMe, H, 70, 105-6°; NO2, CO2Et, H, H, OMe, 63, 128-9°; NO2, CO2Et, F, H, H, 15, 120-2°; NO2, CO2Et, H, F, H, 69, 79-80°; NO2, CO2Et, H, H, F, 52, 138-9°; NO2, CO2Et, H, H, SO2Me, 13, 149-50°; CO2Et, NO2, H, H, H, 29, 111-12°; CO2Et, NO2, OMe, H, H, 41, 112-13°; CO2Et, NO2, H, OMe, H, 46, 81-2°; CO2Et, NO2, H, H, OMe, 56, 120-2°; CO2Et, NO2, F, H, H, 18, 105°; CO2Et, NO2, H, F, H, 59, 119-20°; CO2Et, NO2, H, H, F, 34, 121-2°; CO2Et, NO2, H, H, SO2Me, 10, 189-90°; NO2, CF3, H, H, H, 63, 84°; NO2, CF3, OMe, H, H, 39, 123-4°; NO2, CF3, H, OMe, H, 81, 67-8°; NO2, CF3, H, H, OMe, 80, 85-6°; NO2, CF3, F, H, H, 76, 77-8°; NO2, CF3, H, F, H, 70, 93°; NO2, CF3, H, H, F, 54, 77-8°; NO2, CF3, H, H, SO2Me, 10, 149-50°. Nitration of p-ClC6H4SO2Me with KNO3 in concentrated H2SO4 at 80-5° for 3 hrs. gave 81.7% 4,3-Cl(O2N)C6H3SO2Me, m. 121-2° (20% aqueous alc.), which was condensed with PhNH2 to give 92% I (R = NO2, R1 = SO2Me, R2 = R3 = R4 = H), m. 130-1°. A solution of 15 g. 0-ClC6H4CN in fuming HNO3 was allowed to warm to room temperature from 0-4° in 1 hr., kept for 1 hr. at room temperature, and mixed with 600 ml. ice-water to give 81.8% 2,5-Cl(O2N)C6H3CN, m. 108° (EtOH), which was condensed with PhNH2 in the presence of NaOAc to give 78% I (R = CN, R1 = NO2, R2 = R3 = R4 = H), m. 159-60°. Similarly prepared was I (R = NO2, R1 = CN, R2 = R3 = R4 = H), m. 121-2°. A suspension of 21.7 g. 4,2-Br(O2N)C6H3NH2 in 85 ml. concentrated HCl at 0-4° was diazotized with NaNO2, stirred 1 hr. at 5°, mixed with 15 g. CuCl2 in 50 ml. concentrated HCl, warmed to 70° in 1 hr., and stirred for 30 min. at 70° and overnight at room temperature to give 50% 5,2-Br(Cl)C6H3NO2, m. 70-1° (20% aqueous alc.), which was condensed with PhNH2 to give 80.5% I (R = NO2, R1 = Br, R2 = R3 = R4 = H), m. 54-6°. Similarly prepared were I (R = Br, R1 = NO2, R2 = R3 = R4 = H), m. 111-12°. I (R = NO2, R1 = F, R2 = R3 = R4 = H), m. 120-1°, and I (R = F, R1 = NO2, R2 = R3 = R4 = H), m. 134°. Nitration of 4-ClC6H4CHO gave 80% 4,3-Cl(O2N)C6H3CHO, m. 65-6° (EtOH), which was condensed with PhNH2 in the presence of NaOAc to give a mixture of I (R = NO2, R1 = CHO, R2 = R3 = R4 = H), m. 147-8°, and 4,3-PhNH(O2N)C6H3CH:NPh, m. 108-9°. Similarly prepared was 2,5-PhNH(O2N)C6H3CHO, m. 182° (by-product and m. 132-3°). Attempted conversion of II with 2-, 3-, or 4-FC6H4NH2 or with 3-MeOC6H4NH2 in refluxing HCONMe2 gave 75-85% 2,4-Cl(O2N)C6H3NMe2, m. 78°. Similarly, III and 2- or 4-F3CC6H4NH2 in HCONMe2 gave 4,3-Me2N(O2N)C6H3SO2NH2, m. 133-4°, while IV with all arylamines in HCONMe2 gave 2,5-Me2N(O2N)C6H3SO2NH2, m. 147-8° (EtOH). The experimental process involved the reaction of 3-Chloro-4-nitrobenzonitrile(cas: 34662-29-8).Reference of 3-Chloro-4-nitrobenzonitrile

The Article related to diphenylamines disperse dye, dye diphenylamines disperse, disperse dye diphenylamines, dyes and other aspects.Reference of 3-Chloro-4-nitrobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Grivsky, E. M. published an article in 1971, the title of the article was Convenient synthesis of chloronitrobenzonitrile isomers and homologs.Application of 34662-29-8 And the article contains the following content:

Ten position isomers of chloronitrobenzonitrile and some homologs were prepared from the corresponding benzoic acids and MeSO2NH2 in the presence of PCl5. This method was more generally applicable than the previous procedure using p-toluenesulfonamide and the products were obtained in amounts approaching the theoretical yields. A cyclic mechanism for a transformation leading to the formation of these aromatic nitriles was postulated. Thus, 0.1 mole 3-chloro-5-nitrobenzoic acid was treated with 0.1 mole MeSO2NH2 and 0.2 mole PCl5. After an initial exothermic reaction during which the internal temperature rose to 50-60°, the mixture was heated 30 min at 180° and the product worked up to give 3-chloro-5-nitrobenzonitrile (I). The experimental process involved the reaction of 3-Chloro-4-nitrobenzonitrile(cas: 34662-29-8).Application of 34662-29-8

3-Chloro-4-nitrobenzonitrile(cas:34662-29-8) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Application of 34662-29-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kalir, Asher; Pelah, Zvi published an article in 1966, the title of the article was 6-Trifluoromethylindole.Related Products of 13544-06-4 And the article contains the following content:

4-Trifluoromethylchlorobenzene was treated with HNO3-H2SO4 at 60-5° for 30 min. and the resulting 2-nitro-4-trifluoromethylchlorobenzene was heated with NCCHNaCO2Et at 110-20° for 3 hrs. to give ethyl α-cyano-2-nitro-4-trifluoromethylphenylacetate. This compound was refluxed 12 hrs. with AcOH and H2SO4 until no more CO2 was evolved. The resulting 2-nitro-4-trifluoromethylbenzyl cyanide was purified by distillation (b.p. 134-8°) and reduced by H in the presence of Pd catalyst to give the title compound, b.p. 109-10°. The experimental process involved the reaction of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile(cas: 13544-06-4).Related Products of 13544-06-4

2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile(cas:13544-06-4) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Related Products of 13544-06-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ferris, James P.; Orgel, L. E. published an article in 1965, the title of the article was Aminomalononitrile and 4-amino-5-cyanoimidazole in hydrogen cyanide polymerization and adenine synthesis.Reference of 2-Aminomalononitrile 4-methylbenzenesulfonate And the article contains the following content:

Aminomalononitrile (I) was prepared by the treatment of oximinomalononitrile with Al-Hg; p-toluenesulfonate derivative m. 180-1°. Treatment of I with acid anhydride gave the corresponding oxazoles (II). I is converted to III by reaction with formamidine acetate (IV). Further treatment of III with IV gave adenine. KCN and I react at pH 9-10 to give a brown polymer and diaminomaleonitrile (V). V is the most prominent low-mol.-weight product formed during the polymerization of HCN. The results indicate that I is a key intermediate in HCN polymerizations and possibly prebiol. organic synthesis. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Reference of 2-Aminomalononitrile 4-methylbenzenesulfonate

2-Aminomalononitrile 4-methylbenzenesulfonate(cas:5098-14-6) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Reference of 2-Aminomalononitrile 4-methylbenzenesulfonate

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts