Month: August 2021

Application of 194853-86-6, These common heterocyclic compound, 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, 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.

Weigh 508mg of 5,5-dimethylhein into eggplant-shaped bottles, add 5mL of DMF with stirring to completely dissolve it, then add 220mg of K2CO3 (1eq), stir at 45 C for half an hour to make them mix well. Finally, the DMF solution of 4-fluoro-2-trifluoromethylbenzonitrile (300 mg) was slowly added, and stirred under heating for 5 hours. After the reaction was fully completed, it was cooled to room temperature and diluted with 30 mL of ethyl acetate. It was extracted 3 times with 20 mL of saturated ammonium chloride aqueous solution and once with saturated brine. The organic layer was dried over anhydrous magnesium sulfate for 6 h, filtered with suction, and concentrated. Finally, 200-300 mesh column chromatography was performed to obtain 330 mg of a white solid. Yield 79%.

The synthetic route of 194853-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou University; Ke Yu; Xie Hang; Liu Hongmin; Xu Xia; Liang Jianjia; (25 pag.)CN110759897; (2020); A;,
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50846-36-1, name is 2-Amino-2-methylpropanenitrile hydrochloride, 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. COA of Formula: C4H9ClN2

To a solution of Compound 20 (20 mg), 2-amino-2-methylpropanenitrile hydrochloride (9.32 mg, 0.077 mmol) and HATU (22.05 mg) in DMF (2 mL) was added iPr2NEt (0.027 mL). The mixture was stirred at room temperature for 4 hours. The product was isolated by preparative HPLC system

The synthetic route of 50846-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Wang, Tao; Eastman, Kyle J.; Zhang, Zhongxing; Parcella, Kyle E.; Yin, Zhiwei; Kadow, John F.; US2015/266886; (2015); A1;,
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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. 630-18-2, name is Pivalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C5H9N

Pivalonitrile (1.3 mL, 12.0 mmol) was dissolved in anhydrous ethanol (28 mL) under an atmosphere of Ar. The solution was cooled to 0 C, saturated with HC1 gas, stirred for 6 h, allowed to warm to RT, and stirred for 54 h. The solvent was removed in vacuo to afford ethyl pivalimidate hydrochloride (2.0 g, 100 %) as an off white solid. H NMR (400 MHz, DMSO-i: delta 1 1.19 (br s, 1 H), 4.42 (q, J = 6.9 Hz, 2 H), 1.33 (t, J= 6.8 Hz, 3 H), 1.24 (s, 9 H).

The synthetic route of 630-18-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; BRANDT, Gary E. L.; TELIKEPALLI, Hanumaiah; CALDWELL, Timothy Malcolm; SAMARAKOON, Thiwanka; FLYNN, Daniel L.; KAUFMAN, Michael D.; WO2014/145023; (2014); A1;,
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Application of 87376-25-8, These common heterocyclic compound, 87376-25-8, name is 2-Amino-4-nitrobenzonitrile, 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.

General procedure: In a typical procedure, 5-aryl-1H-tetrazoles (1-24) were synthesized by adding aryl nitriles (1 eq.), sodium azide (1.2 eq.), and ammonium chloride (1 eq.) in solvent, the mixture was refluxed for 24 h. Progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, 2.5 mL of 2M NaOH was added and the solution was stirred for half an hour. The reaction mixture was concentrated on reduced pressure, and dissolved in water. 3M HCl was added to the reaction mixture until precipitates formed. The precipitates were filtered and washed with distilled water. The yields of title compounds were found to be moderate to high.

Statistics shows that 2-Amino-4-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 87376-25-8.

Reference:
Article; Fatima, Itrat; Zafar, Humaira; Khan, Khalid Mohammed; Saad, Syed Muhammad; Javaid, Sumaira; Perveen, Shahnaz; Choudhary, M. Iqbal; Bioorganic Chemistry; vol. 79; (2018); p. 201 – 211;,
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Adding a certain compound to certain chemical reactions, such as: 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, 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 103146-25-4, SDS of cas: 103146-25-4

The hydrobromide salt of racemic 4-[4-(dimethylamino)-1-(4′-fluorophenyl)-1-hydroxy-butyl]-3-(hydroxymethyl)-benzonitrile (50 g) was placed into a round bottom flask. Ethyl acetate (125 mL) was added and the mixture was stirred at 25-35 C. Aqueous sodium carbonate solution (19 g in 125 mL water) was added and the mixture was stirred at about 25-35 C. for 20 minutes. The layers were separated. The aqueous layer was extracted with ethyl acetate (125 mL). The organic layers were combined and washed with water (125 mL) followed by 10% sodium chloride solution (125 mL). The organic layer was evaporated under reduced pressure. The obtained residue was mixed with isopropanol (250 mL) and the mixture was heated at 40-50 C. for 10 minutes. (-)-Di-p-toluoyltartaric acid (23.8 g) was added. The mixture was stirred at 40-50 C. for 5 hours. The formed solid was filtered and washed with isopropanol (40 mL). The filtrate was evaporated under reduced pressure. The residue was mixed with ethyl acetate (125 mL). Aqueous sodium carbonate solution (12.3 g in 125 mL water) was added and the mixture was stirred at 25-35 C. for 20 minutes. The layers were separated and the aqueous layer was extracted with ethyl acetate (125 mL). The organic layers were combined and washed with water (125 mL) followed by 10% sodium chloride solution (125 mL). The solvent was evaporated under reduced pressure and the residue was mixed with a solvent mixture containing 3% by volume methanol in ethyl acetate (400 mL). (+) Di-p-toluoyltartaric acid (15 g) was added and the mixture was stirred at 25-35 C. for 3 hours. The mixture was heated to reflux, maintained at that temperature for 2 hours, and was cooled to 25-35 C. The solid was filtered, washed with a solvent mixture containing 3% methanol in ethyl acetate (50 mL) and dried at 50 C. Yield 83.8% of single enantiomer, chiral purity 98.35%.

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-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bolugoddu, Vijaya Bhaskar; Elati, Chandrasekhar Ravi Ram; Cheemalapati, Sasi Kala Venkata Annapurna; Penumandla, Rajagopal; Christy, Arulnathan Prabakar; Vakamudi, Lakshmi Vara Prasad Sree Naga Venkata; US2010/249438; (2010); A1;,
Nitrile – Wikipedia,
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Electric Literature of 1194-65-6, These common heterocyclic compound, 1194-65-6, name is 2,6-Dichlorobenzonitrile, 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.

A mixture of 2,6-dichlorobenzonitrile(100 g, 581mmol),triethylamine(64.5 g, 640mmol) and (NH4)2S (20% aqueous solution, 217 mL, 640mmol) in pyridine (500 mL) was stirred at 50 C for 4 h.The mixture was concentrated under reduced pressure.The residue was dissolved in water (400 mL) and extracted withEtOAc(3 x 300 mL).The combined organic extract was washed with brine (100 mL), dried over Na2SO4, and concentrated under reduced pressure.The residue was re-crystallized withEtOAc/petroleum ether to afford the desired intermediate as a pale yellow solid (105 g, 88% yield).LCMS (ESI) m/z: 206.0 [M+H+].

The synthetic route of 1194-65-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Jun; Van Abbema, Anne; Balazs, Mercedesz; Barrett, Kathy; Berezhkovsky, Leo; Blair, Wade S.; Chang, Christine; Delarosa, Donnie; DeVoss, Jason; Driscoll, Jim; Eigenbrot, Charles; Goodacre, Simon; Ghilardi, Nico; MacLeod, Calum; Johnson, Adam; Bir Kohli, Pawan; Lai, Yingjie; Lin, Zhonghua; Mantik, Priscilla; Menghrajani, Kapil; Nguyen, Hieu; Peng, Ivan; Sambrone, Amy; Shia, Steven; Smith, Jan; Sohn, Sue; Tsui, Vickie; Ultsch, Mark; Williams, Karen; Wu, Lawren C.; Yang, Wenqian; Zhang, Birong; Magnuson, Steven; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4370 – 4376;,
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Some common heterocyclic compound, 34662-30-1, name is 3-Chloro-5-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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. Quality Control of 3-Chloro-5-nitrobenzonitrile

3-Chloro-5-nitrobenzonitrile was reduced to 3-amino-5-chlorobenzonitrile by treating with 6 equivalents of SnCl2 dihydrate in DMF at RT overnight. The product was purified by chromatography over silica gel (40% yield). LCMS (Cond. A) RT 1.61 min., MH+ 153. 1H NMR (500 MHz, CDCl3) delta 6.97 (s, 1H), 6.84 (t, J=2.0 Hz, 1H), 6.77 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 34662-30-1, its application will become more common.

Reference:
Patent; Gerritz, Samuel; Shi, Shuhao; Zhu, Shirong; US2006/287287; (2006); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 41963-20-6, name is 4-Bromo-3-methylbenzonitrile, 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 41963-20-6, Recommanded Product: 4-Bromo-3-methylbenzonitrile

To a solution of 17 (10.0 g, 49.5 mmol) in carbon tetrachloride (200 mL) were added N-bromosuccinimide (8.81 g, 49.5 mmol) and 2,2′-azobis(isobutyronitrile) (414 mg, 5 mol %), and the mixture was refluxed for 3 h. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue were added dimethylformamide (150 mL) and sodium acetate (20.5 g, 250 mmol), and the mixture was stirred at 80 C. overnight. Water was added, and the mixture was extracted with ether. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue was added methanol (150 mL) and 1 mol/L sodium hydroxide (50 mL), and the mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated to about a third of volume under reduced pressure. Water and hydrochloric acid were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (3:1 hexane/ethyl acetate) followed by trituration with dichloromethane to give 2-bromo-5-cyanobenzyl alcohol (4.63 g, overall 44%): 1H NMR (300 MHz, DMSO-d6) delta (ppm) 4.51 (d, J=5.9 hz, 2H), 5.67 (t, J=5.6 Hz, 1H), 7.67 (dd, J=8.2, 2.0 Hz, 1H), 7.80 (s, J=8.2 Hz, 1H), 7.83 (d, J=2.0 Hz, 1H).

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

Reference:
Patent; Anacor Pharmaceuticals; US2007/265226; (2007); A1;,
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Application of 134604-07-2, These common heterocyclic compound, 134604-07-2, name is 1-Cyano-2-bromo-5-nitrobenzene, 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.

Step 1 2-Cyano-4′-methyl-4-nitrobiphenyl To a solution of p-tolyltrimethyltin (389 mg, 1.525 mmol) in dry toluene (5 mL) under N2 was added 2-bromo-5-nitro-benzonitrile (276 mg, 1.22 mmol) and Pd(PPh3)4 (176 mg; 10 mol %). The reaction was stirred at reflux under N2 for 24 hours and then cooled to room temperature. The mixture was diluted with EtOAc and the solid was removed by filtration through a pad of celite. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on a silica column eluding with Hex/EtOAc (10:1) to afford 214 mg (74%) of the titled compound as a slightly yellow solid. 1 H-NMR: (300 MHz, CDCl3) delta 2.42 (s, 3H), 7.32 (d, 2H), 7.48 (d, 2H), 7.69 (d, 1H), 8.45 (dd, 1H), 8.61 (s, 1H).

Statistics shows that 1-Cyano-2-bromo-5-nitrobenzene is playing an increasingly important role. we look forward to future research findings about 134604-07-2.

Reference:
Patent; Merck & Co., Inc.; US5240928; (1993); A;,
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68385-95-5, name is 2-Amino-3,5-dibromobenzonitrile, 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. category: nitriles-buliding-blocks

To a solution of 2,4-dibromo-6-cyanoaniline (200.00 g, 724.82 mmol) and DMAP(17.71 g, 144.96 mmol) in DCM (3 L), Boc2O (474.58 g, 2.17 mol) was added and thereaction mixture was stirred at 45 C for 4 h. The crude mixture was successively washed with saturated NaHCO3 (2 x 1 L) and brine (2 x 1 L), dried over MgSO4, filtered and concentrated under vacuum to give 323 g of intermediate 1 (56% yield, yellow solid, 86% purity evaluated by LC/MS). The product was used in the next stepwithout any further purification.

The synthetic route of 68385-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
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