Tag: M.W=300-400

Reference of 103146-25-4,Some common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, molecular formula is C20H23FN2O2, 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.

To a stirred solution [OF RACEMIC 4- [4-DIMETHYLAMINO-1- (4-FLUORO-PHENYL)-1-HYDROXY-] [BUTYL]-3-HYDROXYMETHYL-BENZONITRILE] (0,29 mmol, 100 mg) and vinylbutyrate (0,29 mmol, [37 L)] in anhydrous toluene (2,925 ml) is added Novozymes 435, (0,2 mg) and 1,1 eq. Carboxylic acid. The reaction is heated to 40 degrees celcius and followed by HPLC. The enzyme is filtered off and washed with a small amount of toluene. The combined organic phases are evaporated in vacuo and subsequently analyzed on super critical fluid chromatography. Result is shown in table 19.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, its application will become more common.

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

Application of 103146-25-4, These common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)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.

To a solution of Racemic cyanodiol (300g, 0.88 moles) in isopropyl alcohol (1800 ml) at 25-35C (+)-Di-p-toluoyl-D-tartaric acid (169.2g, 0.44 mole) was added. The reaction mixture was then heated and maintained at 60-70 C for lhour. After maintaining was over the reaction mass was cooled and maintained at 28- 32 C for 2-4 hours. The precipitated solid was then filtered, washed with isopropyl alcohol (300 ml) and suck dried for 30minutes. The filtrate was preserved for the recovery of Racemic cyanodiol and (+)-Di-p-toluoyl-D-tartaric acid. The obtained wet cake of (S)-cyanodiol – (+)-DPTTA was suspended in isopropyl alcohol (1200 ml), heated and maintained at 55-65C for 60 minutes. After maintaining was over the reaction mass was cooled to 28-32C where it was maintained for 60 minutes. The precipitated solid was then filtered, washed with isopropyl alcohol (300 ml) and finally dried under vacuum at 60-70 C which provided the title compound (VI) as a white solid. The obtained filtrate was combined with the earlier obtained filtrate for the recovery of Racemic cyanodiol and (+)-Di-p-toluoyl-D-tartaric acid. Yield: 145g (61.96% by Theory) Purity by HPLC: 99.71% Chiral Purity: S-Isomer – 99.59% R-Isomer – 0.41%

Statistics shows that 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 103146-25-4.

Reference:
Patent; IPCA LABORATORIES LIMITED; REGURI, Buchi Reddy; PRASAD, Ashok; RAWAT, Ajay Singh; RAJPUT, Sandip; SANTAN, Rohit B; (36 pag.)WO2017/9866; (2017); A1;,
Nitrile – Wikipedia,
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Reference of 906673-45-8,Some common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, molecular formula is C14H10BrNO2, 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.

40.0 g (131 mmol) of 4-(4-bromo-3-hydroxymethyl-phenoxy)-benzonitrile of formula (II), prepared as described in Example 3, are added under nitrogen to 400 mL THF and 23.8 g (236 mmol) of triethylamine in a previously anhydrified flask. The solution is cooled down to 0 C. and 16.9 g (157 mmol) of trimethylsilyl chloride are added maintaining the temperature below 15 C. After completion of the addition, the mixture is allowed to reach room temperature. 50 mL of toluene and 100 mL of water are added and the phases are separated. The organic phase is washed with a saturated NaCl solution and evaporated to dryness under reduced pressure to obtain 49.4 g of 4-(4-bromo-3-trimethylsilanoxymethyl)-benzonitrile of formula (II) as a solid with a yield of 98%. The obtained product is used in the next step any without further purification. 1H-NMR (CDCl3, 300 MHz) delta (ppm): 7.63-7.60 (2H, m) 7.52 (1H, d, J=8.4 Hz), 7.22 (1H, m) 7.03-7.00 (2H), 6.85-6.80 (1H, m) 4.69 (2H, s), 0.17 (9H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, its application will become more common.

Reference:
Patent; DIPHARMA FRANCIS S.R.L.; Santillo, Niccolo’; Attolino, Emanuele; Brenna, Davide; Vladiskovic, Chiara; Lombardo, Alessandro; Razzetti, Gabriele; US2019/241585; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 103146-25-4, 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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A test tube equipped with a stopper was charged with 10 mg (0.029 m mol) of [(=T :)-4-] [4-dimethylamino-1- (4′-fluorophenyl)-1-hydroxybutyl]-3-hydroxymethylbenzonitrile, 10 mg of Novozym 435 (product of NOvozymes), 33 mg (0.29 [M MOL)] of vinyl butyrate and 1 ml of various kinds of solvents, and stirred at [30C] for 16 hours. After the reaction, converted ratios and optical purities were analyzed and E-values were calculated. The results are shown in Table 9.

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

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 103146-25-4 as follows. Formula: C20H23FN2O2

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.

According to the analysis of related databases, 103146-25-4, the application of this compound in the production field has become more and more popular.

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

Application of 1246213-27-3, 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. 1246213-27-3, name is 2-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-2-methylpropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Pd (OH)2/C (2.0 g) and compound 7 (20.0 g, 0.104 mol) were stirred in MeOH (150 mL) at room temperature under hydrogen at 10 psi pressure for 16-18 hours. The mixture was then filtered through a pad of Celite, and the filtrate was concentrated to give compound 15, which was used in the next reaction without further purification. 1H NMR (DMSO-d6; 400 MHz) delta 9.83 (s), delta 7.24 (s), delta 7.18 (m), delta 6.80 (m), delta 1.71 (s), delta 1.24 (s).

The synthetic route of 2-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-2-methylpropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; DEMATTEI, John; LOOKER, Adam, R.; NEUBERT-LANGILLE, Bobbianna; TRUDEAU, Martin; ROEPER, Stefanie; RYAN, Michael, P.; YAP, Dahrika, Milfred Lao; KRUEGER, Brian, R.; GROOTENHUIS, Peter, D.J.; VAN GOOR, Frederick, F.; BOTFIELD, Martyn, C.; ZLOKARNIK, Gregor; WO2010/108162; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 906673-45-8, These common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)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.

Compound IV (5.00 g, 16.4 mmol, 1.0 eq) and DHP (2.07 g, 24.6 mmol, 1.5 eq) was dissolved in dichloromethane (40 mL). p-Toluenesulfonic acid (0.28 g, 1.6 mmol, 0.1 eq) was added, and the reaction mixture was stirred. After 5h, TLC showed that the basic reaction of the raw materials was completed, post-processing was carried out, the reaction mixture was quenched by the addition of 50 mL of aqueous sodium hydrogencarbonate solution, extracted with 50 mL of dichloromethane, liquid separation was carried out, the organic phase was washed, dried, concentrated, and the obtained crude product was purified by column chromatography to yield 5.71 g of a yellow oil in a yield of 89%.

The synthetic route of 906673-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Wangshanwangshui Bio-pharmaceutical Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute Suzhou Pharmaceutical Chuangxin Institute; Shandong Tefaman Pharmaceutical Co., Ltd.; Tian Guanghui; Wu Jianzhong; Yu Jianghui; Pang Zhenqiang; Li Junyong; (10 pag.)CN108047261; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 39186-58-8, name is 4-Bromo-2,2-diphenylbutyronitrile, 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 39186-58-8, SDS of cas: 39186-58-8

EXAMPLE 22 To 1.96 parts of piperidine is added 1.91 parts of potassium iodide and 25 parts deionized water under a nitrogen atmosphere. The mixture is gently warmed and 1.65 parts of potassium hydroxide and 7.51 parts of 2,2-diphenyl-4-bromobutyronitrile are added. The temperature is raised to reflux and maintained thereat for 4.5 hours. After cooling to room temperature, the reaction mixture is extracted three times with 14 part portions of ethyl ether. The ether extracts are combined, and extracted four times with 25 parts by volume portions of a dilute acetic acid solution. The acid extracts are combined, neutralized to about pH 10 with 50% sodium hydroxide solution, and extracted again with ethyl ether. The ether extracts are combined, washed twice with 50 parts by volume portions of a saturated sodium chloride solution, and dried over anhydrous potassium carbonate. The solvent is removed under reduced pressure to afford, as an off-white solid, in 86.1% yield, 2,2-diphenyl-4-piperidinobutyronitrile. This compound melts at 74 – 77 C., and is represented by the following structural formula. STR16

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-Bromo-2,2-diphenylbutyronitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; G. D. Searle & Co.; US4086234; (1978); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 906673-45-8, A common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, molecular formula is C14H10BrNO2, 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.

In a three-necked flask, compound II (1.9 g), tetrahydrofuran (57 mL), triisopropyl borate (1.53 g) were added to cool down to -78C, and butyllithium (6.25 mL, 2.5 M concentration) was added dropwise.After completion of the reaction for 30 minutes or more, after completion of the reaction, 1N hydrochloric acid (57 mL) was added to quench the reaction, stirred for 30 minutes or more, and allowed to stand for stratification.The organic phase was concentrated under reduced pressure until no solvent was evaporated. Methanol (20 mL) was added to the obtained oil, concentrated hydrochloric acid (0.5 mL) was stirred at room temperature overnight, and after completion of the reaction, the mixture was concentrated under reduced pressure to obtain the target compound I (about 1.8 g).

The synthetic route of 906673-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yaoyuan Pharmaceutical Chemical (Shanghai) Co., Ltd.; Wang Yuan; Liu Chuanjun; Tang Wensheng; He Xungui; (8 pag.)CN107759625; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 1246213-27-3, name is 2-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-2-methylpropanenitrile, 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 1246213-27-3, name: 2-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-2-methylpropanenitrile

To a stirred solution of compound 7 (20 g, 0.065 mol) in toluene (300 mL), was added drop wise DIBAH (80 mL, 1 M in toluene) at about -60 to -50 0C. After stirring for 2 hours, 6 N HCl (300 mL) was added to the reaction mixture and stirring was continued for 30 minutes. The organic layer was then separated, washed with 2 N HCl followed by a NaHCtheta3 solution, then a brine solution, dried over Na2SO4 and concentrated in vacuo to afford the compound 8 as an oil. The product was used in the next reaction without further purification. 1H NMR (CDCl3; 400 MHz) delta 9.61 (s), delta 7.36 (m), delta 7.25 (m), delta 6.87 (m), delta 5.06 (m), delta 1.43 (S), delta 1.33 (s).

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; VERTEX PHARMACEUTICALS INCORPORATED; DEMATTEI, John; LOOKER, Adam, R.; NEUBERT-LANGILLE, Bobbianna; TRUDEAU, Martin; ROEPER, Stefanie; RYAN, Michael, P.; YAP, Dahrika, Milfred Lao; KRUEGER, Brian, R.; GROOTENHUIS, Peter, D.J.; VAN GOOR, Frederick, F.; BOTFIELD, Martyn, C.; ZLOKARNIK, Gregor; WO2010/108162; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts