Category: 63069-50-1

63069-50-1, Name is 4-Amino-3-fluorobenzonitrile, 63069-50-1, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

General procedure: To the solution of compound 15 (0.2 mmol) and 2-aminobenzonitrile (0.6 mmol) in n-BuOH (3 mL) was added DIPEA (0.6 mmol). After stirred at 90 C for 12 h, the reaction mixture was diluted with EtOAc, washed with brine, dried over MgSO4, and evaporated. The residue was purified by column chromatography to give the product 16 as yellow solid. (22 mg, 25%).

Statistics shows that 4-Amino-3-fluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 63069-50-1.

Reference:
Article; Fang, Yuanying; Yang, Zunhua; Gundeti, Shankariah; Lee, Jongkook; Park, Haeil; Bioorganic and Medicinal Chemistry; vol. 25; 1; (2017); p. 254 – 260;,
Nitrile – Wikipedia,
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63069-50-1, 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. 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, A new synthetic method of this compound is introduced below.

Example 57 (2519) 4-((7-Chloro-5-hvdroxy-1 ,1 -dioxido-2H-benzoreiri ,2,41thiadiazin-3-yl)amino)-3- fluorobenzonitrile (2520) To a solution of 3-bromo-7-chloro-5-hydroxy-4H-benzo[e][1 ,2,4]thiadiazine 1 ,1 -dioxide (lnt-3, 200 mg) in t-BuOH (5 ml_) were added 4-amino-3-fluorobenzonitrile (105 mg) and KH2PO4 (105 mg). The reaction mixture was stirred at 1 10 C for 16 hr under nitrogen. The reaction mixture was allowed to cool to RT and was diluted with cold water. The resulting precipitate was collected by filtration and dried under vacuum to afford the crude product (150 mg). The crude product was purified by preparative reversed phase HPLC (XBridge C18, 19×150 mm) using a gradient of 10-55% 0.1 % formic acid/water in acetonitrile. The appropriate fractions were pooled and evaporated under reduced pressure to afford the titled compound (12 mg). LCMS m/z 366.85 (M+H). 1H NMR after D20 exchange (400 MHz, DMSO-c/e) delta ppm 7.12 (d, J=2.19 Hz, 1 H) 7.24 (d, J=2.19 Hz, 1 H) 7.76 (d, J=8.55 Hz, 1 H) 7.92 (dd, J=1 1 .18, 1 .75 Hz, 1 H) 8.43 (t, J=8.33 Hz, 1 H).

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:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; ATOR, Laura E.; DUFFY, Kevin J.; GRAYBILL, Todd L.; KIESOW, Terence John; LIAN, Yiqian; MOORE, Michael Lee; RALPH, Jeffrey M.; RIDGERS, Lance Howard; (370 pag.)WO2017/98421; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

63069-50-1, Adding a certain compound to certain chemical reactions, such as: 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, 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 63069-50-1.

Step 1 : To a stirred solution of 4-amino-3-fluorobenzonitrile (2.0 g, 14.7 mmol) and potassium thiocyanide (5.7 g, 59 mmol) in AcOH (50 mL) was added a solution of bromine (2.3 g, 14.7 mmol) in AcOH (5 mL) over 20 min. The mixture was stirred at rt for 20 h, poured into ice-water (100 mL). Ammonium hydroxide solution (28%) was added to pH 8, stirred for 2 h, filtered, washed with water and dried to afford 4-amino-3-fluorobenzonitrile lnt-6a-1

According to the analysis of related databases, 63069-50-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; KINZEL, Olaf; KREMOSER, Claus; SCHMITT, Aaron C.; GEGE, Christian; (205 pag.)WO2016/96115; (2016); A1;,
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

1.6.1. Step i): 2,4-Difluoro-6-iodoaniline Iodine (1 eq, 19.7 g) is dissolved in EtOH (350 mL) at room temperature, and 2,4-difluoroaniline (1 eq, 8 mL) and silver sulfate (1 eq, 24.1 g) are added. The suspension is stirred at room temperature overnight. After completion of the reaction as seen by LC-MS, the silver salts are filtered off and the filtrate is concentrated in vacuo. The residue is dissolved in DCM and washed with sat. Na2S203 (3 x 100 mL). The organic layer is washed with sat. brine, dried over anhydrous sodium sulfate, and purified by column chromatography (silica, petroleum ether/EtOAc; 100:0 to 95:5) to give the desired product.

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; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; QUINTON, Evelyne; JOANNESSE, Caroline, Martine, Andree-Marie; DE BLIECK, Ann; BLANC, Javier; (263 pag.)WO2017/12647; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

63069-50-1, 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 63069-50-1 as follows.

General procedure: To a solution of 1H-pyrrolo[3,2-H]quinoline-3-sulfonyl chloride (140 mg, 0.52 mmol) in pyridine (1.5 mL) was added 4-chloro-2,5-difluoroaniline (90 mg, 0.55 mmol). The reaction mixture was stirred at room temperature for 4h and then evaporated to dryness. The residue was triturated in a mixture of water/acetonitrile (8/2) and sonicated. The solid suspension was filtered, rinsed with water, dried under vacuum at 35C, to afford 105 mgof N-(4-chloro-2,5-difluorophenyl)-1 H-pyrrolo[3,2-h]quinoline-3-sulfonamide 1-118, as a beige solid.Yield: 50%.Basic LCMS Method 1 (ES): 394 (M+H), 99 % purity.1H NMR (400 MHz, DMSO-d6) 6 13.26 (s, 1H), 10.51 (s, 1H), 8.93 (dd, J = 4.4, 1.6 Hz,1 H), 8.46 (dd, J = 8.3, 1.6 Hz, 1 H), 8.04 – 7.65 (m, 3H), 7.59 (m, 1 H), 7.51 (dd, J = 9.8,6.8 Hz, 1H), 7.40 (dd, J = 10.4, 7.0 Hz, 1H).

According to the analysis of related databases, 63069-50-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB PHARMA GMBH; MUELLER, Christa E.; PEGURIER, Cecile; DELIGNY, Michael Louis Robert; EL-TAYEB, Ali; HOCKEMEYER, Joerg; LEDECQ, Marie; MERCIER, Joel; PROVINS, Laurent; BOSHTA, Nader M.; BHATTARAI, Sanjay; NAMASIVAYAM, Vigneshwaran; FUNKE, Mario; SCHWACH, Lukas; GOLLOS, Sabrina; VON LAUFENBERG, Daniel; BARRE, Anais; (493 pag.)WO2018/122232; (2018); A1;,
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