Month: March 2022

Related Products of 51285-26-8 ,Some common heterocyclic compound, 51285-26-8, molecular formula is C6H8ClN3, 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 157.8 g. (1.0 mol) of 2-pyridinecarboxamidine hydrochloride 23, 54.2 g (1.0 mol) of sodium methoxide in 400 ml of dry methanol was stirred for 30 minutes. The sodium chloride was filtered and the filtrate was concentrated to dryness. The residue and 83 g (1.0 mole) of 3-methoxyacrylonitrile 24 were heated (100-160°) together for 3 hours, at this point the evolution of ethanol had stopped and the melt had started to crystallize. The product 25 was cooled to room temperature, suspended in methanol, filtered and dried to obtain 25 125.6 g, (73percent yield).

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. 51285-26-8, Picolinimidamide hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHY THERAPEUTICS LLC; HADARI, Yaron R.; CARTA, Luca; SCHMERTZLER, Michael; WILLIAMS, Theresa M.; REYNOLDS, Charles H.; HUTCHESON, Rebecca; (1452 pag.)WO2018/237084; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 639091-75-1 ,Some common heterocyclic compound, 639091-75-1, molecular formula is C12H16N2O4, 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 2E (2.5 g, 9.91 mmol, 1.00 equiv) and CaC12 (1.65 g) were dissolved in EtOH (30 mL). The solution was cooled to 0C then NaBH4 (1.13 g, 29.87 mmol, 3.01 equiv) was gradually added. The solution was left under agitation overnight atambient temperature then the reaction was halted with the addition of water (50 mL). The mixture was extracted three times with 20 mL of EtOAc. The organic phases were combined, washed twice with 20 mL of NaC1 (sat.) then dried over sodium sulfate, filtered and concentrated under reduced pressure to yield 2.0 g (90 %) of compound 2F in the form of a colourless solid.

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. 639091-75-1, Methyl 2-(Boc-amino)isonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174060; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89978-52-9, Ethyl 2-bromoisonicotinate, 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, 89978-52-9, blongs to pyridine-derivatives compound. Application In Synthesis of Ethyl 2-bromoisonicotinate

A mixture of 1H-indole-3-carbonitrile (0.1 g), 2-bromoisonicotinic acid ethyl ester (0.16 g), potassium phosphate (0.27 g), (1R,2R)-(-)-N,N’-dimethylcyclohexane-1,2-diamine (0.017 g), copper iodide (0.006 g) and toluene (0.7 mL) was stirred at 110C for 38 hours. The insoluble material was removed by filtration, and this filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane = 10/90 to 66/34) to give the title compound (0.061 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89978-52-9, its application will become more common.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP2133332; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 98197-88-7, 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 98197-88-7 as follows.

A 50-mL round-bottom flask was charged with (4-nitropyridin~2-yl)mefhano (1.07 g, 6 94 mmol), propargyl alcohol (5 mL), and the sodium alkoxide of propargyi alcohol (2.22 g, 28.44 mmol, 4.1 equiv, prepared from propargyiic alcohol and NaH). A reflux condenser was attached, and after the reaction mixture was heated to reflux for 2 h, the reaction mixture was cooled to 23 C, quenched with saturated aqueous NF C (5 mL), and extracted with CH2G2 (3 x 10 mL) using a separatory funnel. The combine organic layers were dried over anhydrous Na2504, filtered, and concentrated in vacuo to deliver (4- (prop-2~yn-1~yoxy)pyridin-2~yl)methanol (830 mg, 73% yield). The crude materia was used directly in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98197-88-7, its application will become more common.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; KOIDE, Kazunori; BEIN, Kiflai; BRESSIN, Robert, Kruger; BURROWS, James, Proviano; GAMBINO, Adriana; LEIKAUF, George, D.; PHAM, Dianne; (80 pag.)WO2020/27905; (2020); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 64064-71-7, 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. 64064-71-7, name is 6-Bromo-3-nitroimidazo[1,2-a]pyridine, molecular formula is C7H4BrN3O2, 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.

C. 3-Nitro-6-(2-pyridylthio) imidazo [1,2-a] pyridine A solution of 1.61 g. (0.012 mole) of the sodium salt of 2-mercapto pyridine and 2.42 g. (0.01 mole) of 6-bromo-3-nitroimidazo [1,2-a] pyridine in 10 ml. N-methylpyrolidinone is heated at 150 C for 40 minutes under a nitrogen atmosphere. The cooled solution is poured onto 100 ml. of ice-water and the resultant suspension is extracted with ethyl acetate. The combined extracts are washed with saturated aqueous sodium chloride and dried over magnesium sulfate. Evaporation of the solvent to a small volume and dilution with N-hexane yields crystalline material. The solids are purified by chromatography on silica gel. Elution with methylene chloride yields pure 3-nitro 6-(2-pyridylthio) imidazo [1,2-a] pyridine.

According to the analysis of related databases, 64064-71-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc.; US4105767; (1978); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1201187-18-9, 6-Chloro-4-(trifluoromethyl)nicotinonitrile, 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, Recommanded Product: 6-Chloro-4-(trifluoromethyl)nicotinonitrile, blongs to pyridine-derivatives compound. Recommanded Product: 6-Chloro-4-(trifluoromethyl)nicotinonitrile

General procedure: To a stirred solution of 1Hpyrazole4carbaldehyde (1.00 g, 10.40 mmol) and 6bromo4methylnicotinonitrile (2.05 g, 10.40 mmol) in dioxane (15 mL) were added K2CO3 (4.31 g, 31.20 mmol). The resulting reaction mixture was degassed with nitrogen for 5 minutes then copper (I) iodide (0.59 g, 3.12 mmol) was added, followed by transN,N’dimethylcyclohexane1,2diamine (2.59 mL, 16.4 mmol). The resulting mixture was degassed again for 10 minutes and heated at 110 C for 1 h under microwave irradiation. The reaction mixture was cooled to ambient temperature, filtered through Celite and the organic layer was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep24 g, 2040% EtOAc/ nhexane) to obtain Intermediate 6 (1.15 g, 52.10%) as pale yellow solid. 1H NMR (300 MHz, DMSOd6) G^ppm 2.62 (s, 3 H), 8.10 (s, 1 H), 8.38 (s, 1 H), 8.95 (s, 1 H), 9.37 (s, 1 H), 9.98 (s, 1 H). LCMS (methodD), retention time 1.68 min, [M+H] 213.2.

The synthetic route of 1201187-18-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 1060814-91-6, name is Ethyl 2-(4-bromopyridin-2-yl)acetate. This compound has unique chemical properties. The synthetic route is as follows. name: Ethyl 2-(4-bromopyridin-2-yl)acetate

To a solution of compound 2-7 (1.3 g, 5.33 mmol, 1 eq) in dimethylformamide (2 mL) was added sodium hydride (533 mg, 13.32 mmol, 60% purity in mineral oil, 2.5 eq) at 0C under nitrogen atmosphere. The mixture was stirred at 0C for 20 minutes and methyl iodide (3.78 g, 26.63 mmol, 1.66 mL, 5 eq) was added. The mixture was stirred at 20C for 10 minutes. TLC (petroleum ether: ethyl acetate = 5:1) indicated the starting material was consumed completely and a new spot was formed. The mixture was poured into water (10 mL) and 1N hydrochloric acid (4 mL). The mixture was adjusted to pH = 8 with sodium bicarbonate solid and extracted with ethyl acetate (20 mLx3). The combined organic phase was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford compound 2-21 (1.44 g, 4.90 mmol, 91.92% yield) as yellow oil. LCMS: RT = 1.408 min, purity: 92.52 %, m/z 271.9,273.9 [M+H]+.1H NMR (CDCl3, 400 MHz): d 8.38 (d, J = 7.2 Hz, 1H), 7.48 (d, J = 2.0 Hz, 1H), 7.34 (dd, J1 = 7.2 Hz, J2 = 2.4 Hz, 1H), 4.17 (q, J = 9.6 Hz, 2H), 1.61 (s, 6H), 1.21 (t, J = 9.2 Hz, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 1060814-91-6.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; TRI-INSTITUTIONAL THERAPEUTICS DISCOVERY INSTITUTE, INC.; FUSHIMI, Makoto; SCALTRITI, Maurizio; HELLER, Daniel, Alan; MONTERRUBIO MARTINEZ, Carles; ARRUABARRENA ARISTORENA, Amaia; MEINKE, Peter, T.; FOLEY, Michael, Andrew; ASANO, Yasutomi; ASO, Kazuyoshi; TAKAHAGI, Hiroki; SHAMAY, Yosef; BASELGA TORRES, Jose, Manuel; SASAKI, Yusuke; MICHINO, Mayako; (271 pag.)WO2020/72892; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 135124-71-9, 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.135124-71-9, name is 5-(Hydroxymethyl)nicotinonitrile, molecular formula is C7H6N2O, molecular weight is 134.14, as common compound, the synthetic route is as follows.

To a stirred solution of 5-(hydroxymethyl)nicotinonitrile (3 g, 0.022 mol) in DCM (30 mL), 4M HC1 in l,4-dioxane (5 mL) was added and concentrated the mixture under vacuum. To the resulting residue, thionyl chloride (20 mL) was added and stirred the mixture at 60 C for 3h. After completion, the reaction was cooled to room temperature and diluted with toluene (150 mL) and filtered off the solid that precipitated out. The filtrate was diluted with DCM (200 mL) and washed with saturated sodium bicarbonate solution (200 mL). The organic layer was dried over sodium sulphate and concentrated to obtain 5-(chloromethyl)nicotinonitrile (Yield: 1.2 g, 35%) as yellow solid. 1H NMR (400 MHz, DMSO-d6, ppm): d 4.86 (s, 2H), 8.42 (s, 1H), 8.94 (d, / = 2.0 Hz, 1H), 8.99 (d, J = 2.0 Hz, 1H). Scheme -9: Synthesis of 3-(hydroxymethyl)-[l,l’-biphenyl]-2-carbonitrile

Statistics shows that 135124-71-9 is playing an increasingly important role. we look forward to future research findings about 5-(Hydroxymethyl)nicotinonitrile.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; D A, Jeyaraj; PENDYALA, Muralidhar; SIVANANDHAN, Dhanalakshmi; RAJAGOPAL, Sridharan; (233 pag.)WO2019/175897; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 51454-63-8, 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.51454-63-8, name is 2-(Hydroxymethyl)isonicotinonitrile, molecular formula is C7H6N2O, molecular weight is 134.14, as common compound, the synthetic route is as follows.

To a cooled solution of oxalyl chloride (13.2mL, 150mmol) in anhydrous DCM (86mL) under nitrogen atmosphere at -78C was added DMSO (21.2ml_ dropwise over 20 minutes. The mixture was stirred for 15 minutes at (-78C) before 2-hydroxymethyl-isonicotinonitrile (4.0g, 30 mmol) dissolved in anhydrous DCM (60mL) was added dropwise to the reaction mixture over 5 minutes. The reaction was stirred for 2 hrs at -78C maintaining a nitrogen atmosphere. A white solid precipitate formed and the temperature was raised to (-55C) and triethylamine (6.15mL, 450mmol) was added dropwise for over 15 minutes, cooling bath was removed allowing the mixture to warm to room temperature over 2 hrs. The mixture was diluted with DCM (400ml_) and washed with brine (2x 50mL). The aqueous phase was extracted with DCM (3x 50 ml_). The combined organic layers were combined and concentrated in vacuo. A buff white solid was isolated that was used without any further purification. Single peak in LC-MS analysis, (yield taken to be quantitative), m/z (LC-MS, ESP), RT=2.53mins, (M+H)=133.0.

Statistics shows that 51454-63-8 is playing an increasingly important role. we look forward to future research findings about 2-(Hydroxymethyl)isonicotinonitrile.

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2006/21801; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59782-90-0, 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 59782-90-0 as follows.

Under the protection of nitrogen, into the three-necked flask, add 53g benzylamine. Then use ice-bath to cool to 3 C. Then continue to add dropwise n-propanal 28g. Control dropwise addition time to 1h. Then add dropwise in batches 13g mass concentration of 10% KOH. Add dropwise 3 time. Then allow the layers to separate. To the organic phase, add 5g mass concentration of 10% KOH. Allow to stand overnight to prepare N-propylidenebenzylamine; Into a 250 ml four-necked flask, add 68g of the above-mentioned prepared N-propylidenebenzylamine. Then add 105 ml dichloromethane and triethylamine 47g. Stir and cool to 0 C, Then continue adding dropwise chloroacetyl chloride 57g. Control the dropwise addition at 1h. Then elevate temperature to 20 C. Continue reacting for 10 min; After the reaction is finished, the deionized water washing and the mass fraction of 10% hydrochloric acid pickling and the mass concentration is 10% of sodium hydroxide caustic wash, finally by reduced pressure distillation to remove the solvent, the reaction liquid prepared, subsequently heating the reaction liquid to column chromatography separation, collection acyl compound; In a 250 ml three-necked flask, add 23g dimethylformamide and 100 ml of 1,2-dichloromethane. Then stir and cool to 0 C. Then take 5.8g triphosgene. Use 50 ml of 1,2-dichloroethane to dissolve. Then add dropwise to the three-necked flask. Control the dropwise addition at 1h. After the completion of the dropwise addition, continue adding dropwise 4.4g of above-mentioned prepared acyl compound. Heat to 55 C and stir reaction for 1h; After the completion of reaction, washing with a large amount of deionized water and collecting the organic phase, for mass fraction of 10% sodium hydroxide solution to adjust the pH to 8.0, subsequently to its hierarchical collection of the organic layer, the solvent is removed by reduced pressure distillation column chromatography separation thereof, to collect colorless transparent crystal 2,3-dichloro-5-methylpyridine; 123.1g of nicotinic acid and 10 ml of 2,3-dichloro-5-methylpyridine were stirred and mixed; Elevate temperature to 55 C. Then add 270g phosphorus trichloride. At 70 C, enter chlorine gas for 2h. Continue heating to 150 C. Then 600 ml ethyl acetate and 20g sodium carbonate were added to the above-mentioned solution. Then continue reaction for 2h. Dry and concentrate and then dissolve in 100 ml toluene. Heat to 80 C and slowly enter phosgene. After reacting for 2h, the sodium carbonate is used to adjust the pH to 7.0, and separating an organic layer to dry the same, subsequently prepared desolution of the 2,3-chloro-5-chloromethyl pyridine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59782-90-0, its application will become more common.

Reference:
Patent; Changzhou University; Chen, Xingquan; (6 pag.)(2016);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem