Tag: M.W:100-200

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine, molecular formula is C7H5ClN2, molecular weight is 152.58, as common compound, the synthetic route is as follows.category: pyridine-derivatives

General procedure: Reference Example 24 6-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile [0267] To a solution of 5-methoxy-2-phenyl-1H-indole (200 mg) in N,N-dimethylformamide (5 mL) was added sodium hydride (dispersed in liquid paraffin, 50% or more, 45 mg) under ice-cooling. This mixture was stirred for 30 minutes at room temperature. Subsequently, 6-chloromethylpyridine-2-carbonitrile (216 mg) was added thereto, followed by stirring at 80C overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (228 mg). [0268] 1H-NMR (DMSO-d6) delta ppm: 3.77 (3H, s), 5.55 (2H, s), 6.55-6.65 (1H, m), 6.77 (1H, dd, J = 2.4, 8.8 Hz), 6.91 (1H, dd, J = 1.5, 7.4 Hz), 7.13 (1H, d, J = 2.4 Hz), 7.26 (1H, d, J = 8.8 Hz), 7.35-7.55 (5H, m), 7.85-7.95 (2H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Kyorin Pharmaceutical Co., Ltd.; TATANI, Kazuya; KONDO, Atsushi; KONDO, Tatsuhiro; KAWAMURA, Naohiro; SETO. Shigeki; KOHNO, Yasushi; EP2669271; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 156072-84-3 ,Some common heterocyclic compound, 156072-84-3, molecular formula is C7H5ClN2, 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 5-chloro-3-methylpicolinonitrile (24.0 g, 157 mmol) in EtOH (100 mL) was added NaOH (110 mL of 5 N solution, 550 mmol). The resulting mixture was refluxed at 90 C. for 18 h. After cooling to RT, the reaction mixture was concentrated. The residue was diluted with water and the pH of the solution was adjusted to 4 by addition of 5 N HCl. The solid that precipitated was filtered and set aside. The filtrate was extracted with EtOAc (2×). The aqueous layer was again acidified with 5 N HCl to pH 4 and extracted with EtOAc (2×). The EtOAc extracts were combined, dried, and concentrated. The solid obtained from all the workup steps were combined and dried in a high vac oven at 40 C. for 12 h to give 5-chloro-3-methylpicolinic acid (268) (24.1 g, 140 mmol, 89% yield). LC/MS (ESI+) m/z=172.0 (M+H)+. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 11.29 (br. s., 1H), 8.41 (d, J=1.76 Hz, 1H), 7.73 (d, J=1.76 Hz, 1H), 2.75 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156072-84-3, its application will become more common.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 15103-48-7 ,Some common heterocyclic compound, 15103-48-7, molecular formula is C5H5NO3S, 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.

1 g of the compound Slic-CJH-5 prepared in the fourth step of Example 2,And 200mgof2-pyridine sulfonic acid and 530 mg of anhydrous sodium carbonate were dispersed in 40 ml of ethylene glycol ether,Under nitrogen protection,The temperature was refluxed for 12 hours,Cooled to room temperature, diluted with dichloromethane, washed three times with water, dried in organic phase,Filtered, the filtrate was concentrated under reduced pressure,The residue was purified by silica gel column and recrystallized from ether-petroleum ether,To obtain 460 mg of the compound Slic-CJH-DB011-VII02,Yellow solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15103-48-7, its application will become more common.

Reference:
Patent; Shijiazhuang Chengzhi Yonghua Xianshi Material Limited Company; Cao, Jianhua; Pang, Hui; Huang, Hongliang; Hua, Ruimao; (36 pag.)CN103896990; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 696-42-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.696-42-4, name is 5-Fluoronicotinonitrile, molecular formula is C6H3FN2, molecular weight is 122.0998, as common compound, the synthetic route is as follows.

To a stirred solution of 5-fluoropyridine-3-carbonitrile (2.0 g, 16.38 mmol) in methanol (20 mL) at RT was added NaOMe (88mg, 1.64 mmol) and the reaction stirred at RT overnight. Ammonium chloride (1 .40g, 26.21 mmol) was added in a single portion and the reaction mixture stirred overnight at RT. The reaction mixture was filtered and the filtrate concentrated to dryness under reduced pressure. The residue was suspended in EtOH (50 mL) and then heated at reflux. The undissolved solid was filtered off and the filtrate concentrated to 1/3 of its volume and then left to stand at RT. The resultant crystals were filtered off, washed with EtOH and air-dried to give the desired product (2.1 1 g, 73%) as white crystals. 1H NMR (400 MHz, d6-DMSO) o 8.93 (d, 1 H), 8.88 (s, 1 H), 8.29-8.23 (m, 1 H).

Statistics shows that 696-42-4 is playing an increasingly important role. we look forward to future research findings about 5-Fluoronicotinonitrile.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WAILES, Jeffrey, Steven; BRIGGS, Emma; CARTER, Neil, Brian; MORRIS, Melloney; TATE, Joseph, Andrew; (61 pag.)WO2019/57722; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1211523-71-5, Adding some certain compound to certain chemical reactions, such as: 1211523-71-5, name is 2-(2-Bromopyridin-3-yl)acetonitrile,molecular formula is C7H5BrN2, 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 1211523-71-5.

To 0C2-(2-Bromopyridin-3-yl)acetonitrile (2.21 g, 11.21 mmol) in DMF (20 mL)Sodium hydride (60% mineral oil dispersion, 1.12 g, 28.03 mmol) was added portionwise to the solution.The reaction system was warmed to 60 C and stirred for 1.5 h.tert-Butyl bis(2-chloroethyl)carbamate (3.26 g, 13.46 mmol) was added to the mixture and stirred at 60 C for 2 h.After cooling to RT, the reaction was quenched with brine (50 mL).Extract with EA (3 x 100 mL). The combined organic phases were washed with brine (3×40 mL).Dry over anhydrous Na2SO4, filtered and evaporated.The residue was purified by silica gel chromatography eluting with EtOAc:EtOAc:4-(2-Bromopyridin-3-yl)-4-cyanopiperidine-1-carboxylic acid tert-butyl ester (1.56 g) was obtained.

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. 1211523-71-5, 2-(2-Bromopyridin-3-yl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Beijing Jiakesi Drug Discovery Co., Ltd.; Ma Cunbo; Gao Panliang; Hu Shaojing; Xu Zilong; Han Huifeng; Wu Xinping; Kang Di; Long Wei; (147 pag.)CN110143949; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.89026-78-8, name is 6-Chloro-N-methylpyridin-2-amine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.Formula: C6H7ClN2

2-Chloro-N-(6-chloropyridin-2-yl)-N-methyl-pyrimidin-4-amine used as starting material was made as follows: NaHMDS (1.5 ml, 1.5 mmol, IN in THF) was added dropwise to a mixture of 2-chloro-6- methylaminopyridine (142 mg, 1 mmol, German Patent, DE3318560, p 9) and 2,4- dichloropyrimidine (222 mg, 1.5 mmol) in THF (20 ml) cooled at -200C. The mixture was stirred at -200C for 2 hours. Acetic acid (a few drops) were added and the mixture was concentrated. The mixture was taken in DCM, filtered and concentrated. The residue was purified by chromatography on silica gel (eluant: 40% to 50% ethyl acetate in petroleum ether) to give 2-chloro-N-(6-chloropyridin-2-yl)-N-methyl-pyrimidin-4-amine (86 mg, 34%). NMR Spectrum: (CDCl3) 3.61 (s, 3H), 6.93 (d, IH), 7.18 (d, IH), 7.28 (m, IH), 7.72 (t, IH), 8.17 (d, IH); Mass spectrum: MH+ 255.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89026-78-8, 6-Chloro-N-methylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/10794; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1019021-85-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1019021-85-2, name is 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a stirring suspension of 6-fluoroimidazo[1 ,2-a]pyridine-3-carboxylic acid (24b) (150 mg, 0.833 mmol) in anhydrous dichloromethane (3 ml_) at 0 C under argon was added dropwise oxalyl chloride (74 muIota_, 0.874 mmol). Then, a drop of anhydrous DMF was added and the reaction mixture was stirred at 0 C for 1 .5 hours. The solvent was concentrated and the crude solid was added to a stirring solution of methyl (3-(3-amino- 4-methylphenyl)-1 ,2,4-oxadiazol-5-yl)methylcarbamate (155) (120 mg, 0.416 mmol) in anhydrous pyridine (3 mL) at 0 C. The reaction was stirred at room temperature under argon for 20 minutes. The solvent was concentrated and the crude product was purified by silica chromatography to give methyl (3-(3-(6-fluoroimidazo[1 ,2-a]pyridine-3- carboxamido)-4-methylphenyl)-1 ,2,4-oxadiazol-5-yl)methylcarbamate (F167). 1 H NMR (400MHz, c/6-DMSO) delta 10.12 (s, 1 H), 9.48 – 9.46 (m, 1 H), 8.63 (s, 1 H), 8.07 (t, J = 5.6 Hz, 1 H), 8.06 (d, J = 1 .6 Hz, 1 H), 7.90 – 7.86 (m , 1 H), 7.82 (dd, J = 2.0, 8.0 Hz, 1 H),7.67 – 7.62 (m, 1 H), 7.50 (d, J = 8.0 Hz, 1 H), 4.57 (d, J = 6.0 Hz, 2H), 3.59 (s, 3H), 2.36 (s, 3H). MS m/z 425.39 (M+1 )+.

According to the analysis of related databases, 1019021-85-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; LIU, Xiaodong; LI, Xiaolin; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; WO2013/33116; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 3430-21-5, 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 3430-21-5 as follows.

Step-I: 6-Amino-5-methyl-pyridine-3-carbonitrile To a mixture of DMF:water (100:2, 102 mL) was added 5-bromo-3-methyl-pyridin-2-amine (10 g, 53.47 mmol), zinc cyanide (3.77 g, 32.1 mmol) and 1,1′-Bis(diphenylphosphino)ferrocene (3.56 g, 6.4 mmol) and degassed for 20 mins. To this was added tris(dibenzylideneacetone)dipalladium (0) (2.45 g, 2.67 mmol) and heated at 120 C. After stirring for 16 h, reaction mixture was cooled to room temperature. To it was added mixture of saturated solution of ammonium chloride: ammonium hydroxide:water (4:1:4, 100 mL). Slurry formed was cooled to 0 C. and again mixture of saturated solution of ammonium chloride: ammonium hydroxide:water (4:1:4, 100 mL) added and stirred for 1 h. Solid formed was filtered through Buchner funnel and dried under high vacuum to get 6.0 g (81%) of titled compound as a tan solid. MS (ES) m/z 134.1 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3430-21-5, its application will become more common.

Reference:
Patent; Kharul, Rajendra; Bhuniya, Debnath; Mookhtiar, Kasim A.; Singh, Umesh; Hazare, Atul; Patil, Satish; Datrange, Laxmikant; Thakkar, Mahesh; US2015/65464; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 18699-87-1, 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. 18699-87-1, name is 2-Methyl-3-nitropyridine, molecular formula is C6H6N2O2, The 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.

Example 1; Scheme A; A mixture of a-1 (0.0072 mol) and paraformaldehyde (0.0058 mol) in DMSO (3.5ml) and triton B (0.27ml) was stirred at 90C for 4 hours, then cooled to room temperature and purified by column chromatography over silica gel (eluent: CH2CI2 then CH2CI2/ CH3OH/NH4OH (99/1/0.1); 15mum). The pure fractions were collected and the solvent was evaporated, yielding: 0.3 g of intermediate a-2 (20%).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 18699-87-1, 2-Methyl-3-nitropyridine.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD; WO2006/136562; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 92276-38-5, Adding some certain compound to certain chemical reactions, such as: 92276-38-5, name is 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine,molecular formula is C5H3BrN4, 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 92276-38-5.

General procedure: To a stirred solution of 6-bromo-1H-i,2,3-triazolo[4,5-b]pyridine (250 mg, 1.26 mmol) in DMF (5 mL) at rt was added 60% sodium hydride in mineral oil (55 mg, 1.38 mmol) and the mixture was stirred at rt for 30 mins. (2-(Chloromethoxy)ethyl)trimethylsilane (419 mg, 2.51 mmol) was added and the mixture was stirred for 15 h. The reaction mixture was partitioned between water and EtOAc and the aqueous layer was separated and further extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0 – 20% EtOAc in hexanes to afford a 1:1 mixture of 6-bromo- 1 -((2- (trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5-b]pyridine and 6-bromo-3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo[4,5 -b]pyridine (240 mg) as an oil, which was not purified further. LC-MS (ESI) mlz 329 and 331 (M+H).v [000223] Step 2: A 1:1 mixture of N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 – yl)-2-(4-(l -((2-(trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5 -b]pyridin-6- yl)phenyl)acetamide and N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)-2-(4-(3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo [4,5 -b]pyridin-6-yl)phenyl)acetamide (71 mg, 40%) was obtained as a solid using a procedure analogous to that described in Step 3 of Example4, substituting the product obtained from Step 1 of this example for the 2-chloro-6,7- dimethoxyquinoxaline used in Example 4 and substituting 2-(4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)acetamide (Ref: S. Abraham et al, WO 2011022473 Al) for the 2-(2-fluoro-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1 -(trifluoromethyl)cyclopropyl)isoxazol-3 -yl)acetamide used in Example 4. LC-MS (ESI) mlz 561 (M+H).[000224] Step 3: To a 1:1 mixture of N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 – yl)-2-(4-(l -((2-(trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5 -b]pyridin-6- yl)phenyl)acetamide and N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)-2-(4-(3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo [4,5 -b]pyridin-6-yl)phenyl)acetamide (71 mg, 0.127 mmol) was added trifluoroacetic acid (5 mL), and the mixture was stirred at rt for 1 h. The mixture was concentrated under reduced pressure and the residue was purified by reverse-phase preparative HPLC using a mixture of water (containing 5% CH3CN and 0.05% HCOOH) and CH3CN (containing 0.05% HCOOH) as the mobile phase and Varian Pursuit XRs diphenyl column as the stationary phase to afford 2-(4-(3H-[l,2,3]triazolo[4,5-b]pyridin-6-yl)phenyl)-N- (5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)acetamide (12 mg, 22%) as a solid. ?H NMR (500 MHz, DMSO-d6) oe 11.41 (br s, 1H), 9.00 (d, J= 2.0 Hz, 1H), 8.60 (br s, 1H), 7.80 (d, J 8.5 Hz, 2H), 7.48 (d,J 8.5 Hz, 2H), 6.95 (s, 1H), 3.77 (s, 2H), 1.53 (s, 6H); LC-MS (ESI) m/z 431 (M+H).

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. 92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; HOLLADAY, Mark, W.; LIU, Gang; ROWBOTTOM, Martin, W.; WO2015/31613; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem