Month: November 2020

Adding some certain compound to certain chemical reactions, such as: 935-02-4, name is 3-Phenylpropiolonitrile, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 935-02-4. 935-02-4

General procedure: To a mixture of acetylene 2 (127 mg, 1 mmol) and S (32 mg, 1 mmol) was added 1-methylimidazole (1a; 82 mg, 1 mmol). The mixture was stirred at 20-25 C for 24 h. Column chromatography afforded thione 3a (132 mg, 67%), 4.3.8 (Z)-3-(3-Allyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl)-3-phenyl-2-propenenitrile (3f) Analogously, from acetylene 2 (127 mg, 1 mmol), S (32 mg, 1 mmol), and 1-allylimidazole (1f; 108 mg, 1 mmol) (20-25 C, 24 h) thione 3f (186 mg, 87%) was obtained as a yellow microcrystalline powder, mp 140-142 C (washed with ether). Initial imidazole 1f was recovered (23 mg, conversion was 79%). 1H NMR (400.13 MHz, CDCl3): delta=7.49-7.29 [m, 5H, Ho,m,p from C(6)-Ph], 6.90 (s, 1H, 4-H), 6.80 (s, 1H, 5-H), 6.07 (s, 1H, 7-H), 6.02-5.92 (m, 1H, Hx from N-Allyl), 5.34 (d, 3JHA,Hx=10.3 Hz, 1H, HA from N-Allyl), 5.28 (d, 3JHB,Hx=17.0 Hz, 1H, HB from N-Allyl), 4.70 (d, =5.9 Hz, 2H, N-CH2 from N-Allyl) ppm. 13C NMR (100.62 MHz, CDCl3): delta=164.3 (C-2), 154.3 (C-6), 132.6 [Ci from C(6)-Ph], 132.0 [Cp from C(6)-Ph], 131.3 (CHx from N-Allyl), 129.3 [Cm from C(6)-Ph], 126.9 [Co from C(6)-Ph], 119.7 (C-4), 118.4 (CHA,HB from N-Allyl), 117.2 (C-5), 114.7 (CN), 97.3 (C-7), 50.3 (CH2 from N-Allyl) ppm. IR (KBr): 2222 (CN), 1621 (C=C), 1398 (C=S) cm-1. Anal. Calcd for C15H13N3S (267.35): C, 67.39; H, 4.90; N, 15.72; S, 11.99. Found: C, 67.26; H, 4.81; N, 15.80; S, 11.69.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3-Phenylpropiolonitrile.

Reference:
Article; Belyaeva, Kseniya V.; Andriyankova, Ludmila V.; Nikitina, Lina P.; Mal’Kina, Anastasiya G.; Afonin, Andrei V.; Ushakov, Igor A.; Bagryanskaya, Irina Yu.; Trofimov, Boris A.; Tetrahedron; vol. 70; 5; (2014); p. 1091 – 1098;,
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These common heterocyclic compound, 185147-08-4, name is 4-Fluoro-3-methylbenzonitrile, its 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. 185147-08-4

To a solution of 4-fluoro-3-methylbenzonitrile (2.5 g, 18.50 mmol) in DMSO (Volume: 10.0 mL) was added piperazine (7.97 g, 92 mmol) at 23 ¡ãC. The reaction was stirred at 140 ¡ãC for 16 hr. The reaction mixture was poured into H2O (100 mL) and the reaction vessel was rinsed with H2O (~50 mL). The resulting suspension was filtered, rinsed with H20 (3 x 10 mL) and the resulting solid was dried in vacuo to provide 3-methyl-4-(piperazin-1-yl)benzonitrile ( 2.593g, 12.88 mmol, 69.6 percent yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) ppm 2.21 – 2.30 (m, 3 H) 2.57 – 2.70 (m, 1 H) 2.83 (s, 8 H) 7.03 – 7.09 (m, 1 H) 7.55 – 7.62 (m, 2 H). ESI-MS: m/z 202.1 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 185147-08-4.

Reference:
Article; Gangloff, Anthony R.; Brown, Jason; De Jong, Ron; Dougan, Douglas R.; Grimshaw, Charles E.; Hixon, Mark; Jennings, Andy; Kamran, Ruhi; Kiryanov, Andre; O’Connell, Shawn; Taylor, Ewan; Vu, Phong; Bioorganic and Medicinal Chemistry Letters; vol. 23; 16; (2013); p. 4501 – 4505;,
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A common compound: 591769-05-0, name is 3-Cyclopentylacrylonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 591769-05-0

To a solution of -4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine (15.0 g,0.0476 mol) in ACN (300 mL) was added 3-cyclopentylacrylonitrile (15 g, 0.12 mol) (as a mixture of cis and trans isomers),followed by DBU (15 mL, 0.10 mol). The resulting mixture was stirred at room temperature overnight. The ACN wasevaporated. The mixture was diluted with ethyl acetate, and the solution was washed with 1.0 N HCl. The aqueous layerwas back-extracted with three portions of ethyl acetate. The combined organic extracts were washed with brine, driedover sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (gradientof ethyl acetate/hexanes) to yield a viscous clear syrup, which was dissolved in ethanol and evaporated several timesto remove ethyl acetate, to afford 19.4 g of racemic adduct (93percent). The enantiomers were separated by preparative-HPLC, (OD-H, 15percent ethanol/hexanes) and used separately in the next step to generate their corresponding final product.The final products (see Step 3) stemming from each of the separated enantiomers were found to be active JAK inhibitors;however, the final product stemming from the second peak to elute from the preparative-HPLC was more active thanits enantiomer.1H NMR (300 MHz, CDCl3): delta 8.85 (s, 1H), 8.32 (s, 2H), 7.39 (d, 1H), 6.80 (d, 1H), 5.68 (s, 2H), 4.26 (dt, 1H),3.54 (t, 2H), 3.14 (dd, 1H), 2.95 (dd, 1H), 2.67-2.50 (m, 1H), 2.03-1.88 (m, 1H), 1.80-1.15 (m, 7H), 0.92 (t, 2H), -0.06(s, 9H); MS(ES):437 (M+1).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 591769-05-0, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Incyte Holdings Corporation; PARIKH, Bhavnish; SHAH, Bhavesh; YELESWARAM, Krishnaswamy; (55 pag.)EP2574168; (2016); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 63069-50-1 name is 4-Amino-3-fluorobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 63069-50-1

Specifically, oxalyl chloride (0.71 mL, 8.24 mmol) was added over 10 min to a solution of oleic acid (2 mL, 6.34 mmol) and DMF (3 drops) in DCM (10 mL) at 0 C, and the solution stirred at room temperature overnight. The solvent and excess oxalyl chloride was removed in vacuo and the residue redissolved in DCM (10 mL). This solution was added dropwise to a solution of 3-fluoro-4-aminobenzonitrile (0.70 g, 5.14 mmol) in DCM (10 mL) and ET.3N (1 mL) that had been cooled in an ice bath. Upon complete addition, the solution was stirred at room temperature overnight. The solution was washed with saturated Na2C03 solution (3 chi 20 mL), H2O (20 mL), and brine (20 mL), and dried over MgS04. The resulting residue was subjected to column chromatography, using a gradient elution of EtOAc/petroleum spirits to afford the product as a white. (0541) [00403] Yield: 1 .59 a (61 %). [00404] FT-I (ATR) V^/crrr1 : 3319 br w. 2919 m. 2850 m. 2236 w. 1681 s. 1616 w. 1589 m, 1519 s. 1 H-NMR delta/ppm (d6-DMSO): 10.07 (1 H, s, NH), 8.33 (1 H, dd, 3JH,H = 8.5 Hz, 4 H,F = 7.9 Hz, Ar CH), 7.89 (1 H, dd, 3JH,F = 1 1 .0 Hz, 4 H,H = 2.0 Hz, Ar CH), 7.66 (1 H, ddd, 3JH,H = 8.5 Hz, 4JH,H = 2.0 Hz, 5JH,F = 0.9 Hz, Ar CH), 5.29 – 5.40 (2 chi 1 H, 2 chi m, 2 chi olefinic CH), 2.47 (2H, m, NHCOCH2) , 1 .96 – 2.04 (2 x 2H, 2 x m, 2 x CH2), 1 .61 (2H, m, CH2), 1 .23 – 1 .37 (10 chi 2H, 10 chi m, 10 chi CH2), 0.87 (3H, m, CH3). 13C-NMR delta/ppm (d6-DMSO): 172.4 (CONH), 151 .6 (d, 1 JC,F = 247 Hz, Ar CF), 131 .7 (d, 2JC,F = 1 1 .1 Hz, Ar C), 129.6 (olefinic CH), 129.5 (olefinic CH), 129.3 (d, 3JC,F = 3.4 Hz, Ar CH), 122.9 (d, 4JC,F = 2.7 Hz, Ar CH), 1 19.2 (d, 2JC,F = 23.3 Hz, Ar CH), 1 17.9 (d, 4JC,F = 2.7 Hz, CN), 105.7 (d, 3JC,F = 9.4 Hz, Ar C), 35.9 (NHCOCH2), 31 .3 (CH2) , 29.09 (CH2), 29.08 (CH2), 28.8 (CH2), 28.7 (CH2), 28.62 (CH2), 28.59 (CH2), 28.55 (CH2), 28.5 (CH2), 26.6 (CH2), 24.9 (CH2), 22.1 (CH2), 13.9 (CH3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; CURTIN UNIVERSITY; FALASCA, Marco; MASSI, Massimiliano; SIMPSON, Peter, Vernon; (181 pag.)WO2019/40992; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

939-80-0, A common compound: 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

4-Chloro-3-nitro-benzonitrile (30 g, 165 mmol) was suspended in EtOH (60 mL), and methylamine (33% in EtOH, 24 ml, 165 mmol) was added. The mixture was stirred at room temperature for 1 h, then heated to 7O0C overnight. The reaction mixture was cooled to rt and concentrated in vacuo. The residue was suspended in Et2O and filtered to give 42 g of 4- methylamino-3-nitro-benzonitrile, which was used in the next step without further purification. 400 MHz 1H NMR (CD3OD) delta (ppm): 8.5 (s, 1 H), 7.70 (d, J = 9 Hz, 1H), 7.09 (d, J = 9 Hz, 1H), 3.29 (s, 3H); APCI” MS+ 177.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Chloro-3-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/12623; (2008); A1;,
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6393-40-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below.

To a stirred solution of 4-amino-3-nitro-benzonitrile (2.00 g, 12.3 mmol) in methanol (20 mL) was added Pd/C (500 mg, 10% purity), then the flask was degassed and filled with hydrogen three times, and the reaction mixture stirred vigorously under hydrogen (balloon) for 18 h at 25 C. The mixture wasevacuated and backfilled with nitrogen three times, then filtered through a pad of celite, and the filtrate concentrated in vacuo to give 3,4-diaminobenzonitrile (1 .47 g, 11 .04 mmol, 90 %) as a green oil that was used in next step directly.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; YUMANITY THERAPEUTICS; LUCAS, Matthew; LE BOURDONNEC, Bertrand; WRONA, Iwona; PANDYA, Bhaumik; TIVITMAHAISOON, Parcharee; OZBOYA, Kerem; VINCENT, Benjamin; TARDIFF, Daniel; PIOTROWSKI, Jeff; SOLIS, Eric; SCANNEVIN, Robert; CHUNG, Chee-Yeun; ARON, Rebecca; RHODES, Kenneth; (489 pag.)WO2018/81167; (2018); A1;,
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25808-30-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

bl . l) Compound (2) To a solution of cyano-N-methylmethanaminium chloride (6.4 g, 39.9 mmol) in chlorobenzene (50 ml) was added dropwise oxalyl chloride (12 ml, 137 mmol) at r. t., then the resulting solution was heated slowly to 90 ¡ãC and stirred overnight. The solvent was removed, the residue was purified by column chromatography on silica gel (PE:EA=10: 1) to give the title compound as yellow oil (5 g, 70percent yield). LC-MS (ESI+): m/e 178 (M+H)+, Rt: 1.54 min.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ABBVIE DEUTSCHLAND GMBH & CO. KG; ABBVIE INC.; GENESTE, Herve; OCHSE, Michael; DRESCHER, Karla; BEHL, Berthold; LAPLANCHE, Loic; DINGES, Juergen; JAKOB, Clarissa; WO2014/140184; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 218632-01-0, 218632-01-0

3- r(2R.3RJS)-7-Methyl-2.3-diDhenyl-14-dioxasDiror4.5ldec-7-yllmethyl amino)-4- nitrobenzonitrileA solution of acetonitrile (2049 ml.) in a 3 L flask was heated to 40 C. Next, potassium carbonate (198 g, 1434 mmol), 1-[(2R,3R,7S)-7-methyl-2,3-diphenyl-1 ,4- dioxaspiro[4.5]dec-7- yl]methanamine (242 g, 717 mmol) and 3-fluoro-4-nitrobenzonitrile (1 19 g, 717 mmol) were added slowly. The mixture was allowed to stir at 40 C for 2 h, and then cooled to RT. Stirring was continued at RT overnight. The next day, the slurry was filtered and the solids were washed with acetonitrile (500 ml_). The filtrate was concentrated to afford the crude product (while keeping the temperature -60 C during concentration). To the thick dark residue was added MeOH. The solution was heated to 60 C on the rotovap and concentrated to a minimal volume. To the residue was added -500 ml. of MeOH slowly with heating to avoid rapid crystallization, and the solution was heated to reflux. Once at reflux, an additional 250 ml. MeOH was slowly added. The resulting slurry was allowed to stir at reflux for about 60 min, then heating was stopped and the slurry was allowed to cool to RT and stirring was continued for 3 days. The slurry was cooled to -10 C with an ice/water bath. Stirring was continued for -2 h, and then the slurry was filtered and washed with cold MeOH (100 ml_). The solids were dried under reduced pressure to give the desired product as a bright orange solid (245 g, 70.7% yield). This material was used in the next step.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Fluoro-4-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; HOANG, Tram, H.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2013/12500; (2013); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 17626-40-3, name is 3,4-Diaminobenzonitrile, A new synthetic method of this compound is introduced below., 17626-40-3

A generic experiment was as follows. In a two-neck roundbottomflask of 10 mL, 1,2-phenylenediamine (1a, 0.5 mmol),1,2-propyleneglycol (2a, 0.6 mmol), 1.5 mL of diethylene glycol dimethylether (diglyme), and an amount of catalyst were added.Subsequently, the reaction mixture was heated at 140 C in a siliconebath that contains a magnetic stirrer and a temperature controller.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Climent; Corma; Hernandez; Hungria; Iborra; Martinez-Silvestre; Journal of Catalysis; vol. 292; (2012); p. 118 – 129;,
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Adding some certain compound to certain chemical reactions, such as: 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 103146-25-4. 103146-25-4

In a 200-ml four-necked flask equipped with a stirrer and a thermometer, 1.5 g [(4.] [38] m mol) of [()-4- [4-DIMETHYLAMINO-1- (4′-FLUOROPHENYL)-1-HYDROXYBUTYL]-3-] hydroxymethylbenzonitrile was dissolved in 30 ml of toluene, then 0.45 g of Novozym 435 (product [OF NOVOZYMES),] 0.347 g (4.38 m mol) of pyridine, 4.38 m mol of various kinds of acids and 1.00 g (8.76 m mol) of vinyl butyrate were added, and stirred at [40C] for between 16 and 21.5 hours. The result is shown in Table 4.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts