Month: April 2022

Application of 832715-99-8 , The common heterocyclic compound, 832715-99-8, name is 6-(tert-Butyl)nicotinic acid, molecular formula is C10H13NO2, 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 3: Preparation of (R)-2-(3-(6-tert-butylnicotinamido)piperidin- 1 -yl)-5-(pyridin-2- ylamino)thiazole-4-carboxamide To a solution of 6-tert-butylnicotinic acid (23.5 mg, 131 imol) and 2-((R)-3-amino-piperidin-1-yl)-5-(pyridin-2-ylamino)-thiazole-4-carboxylic acid amide (38 mg, 119 imol) in N,Ndimethylformamide (1 mL) was added diisopropylethylamine (35 tL, 200 imol) followed by 0- (benzotriazol- 1 -yl)-N,N,N?,N?-tetramethyluronium hexafluorophosphate (61 mg, 161 imol). After stirring at ambient temperature overnight under an atmosphere of argon the reaction was quenched by the addition of saturated aqueous ammonium chloride (2 mL), the mixture pouredinto water (5 mL) and extracted with ethyl acetate (3 x 3 mL). The combined organic extracts were washed with brine (2 x 2 mL), dried over sodium sulfate, filtered and concentrated in vacuo to a yellow solid. The crude product was purified by chromatography using a 13 g C-18 column gradient eluted from 10% acetonitrile in water up to 100% acetonitrile. The product containing fractions were combined and concentrated in vacuo and the residue lyophilized from acetonitrile / water to give (R)-2-(3-(6-tert-butylnicotinamido)piperidin- 1 -yl)-5-(pyridin-2-ylamino)thiazole- 4-carboxamide as a pale yellow solid (37.8 mg, 66 %).LC/MS: mlz calculated for C24H29N702S ([M+Hj): 480.6. Found: 480.3 (positive modeelectrospray ionization).

The synthetic route of 832715-99-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HUBY, Nicholas John Silvester; LOPEZ-TAPIA, Francisco Javier; SO, Sung-Sau; WO2014/90715; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1062368-71-1, 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 1062368-71-1, name is Methyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

A solution of methyl 4-bromopyrazolo [1 ,5-ajpyridine-3-carboxylate (500 mg, 1.97 mmol), potassium trifluoro(2-methoxyethyl)borate (490 mg, 1.28 mmol), RuPhos (734 mg, 1.58 mmol), Pd(OAc)2(177 mg, 0.79 mmol) and C52CO3(1.92 g, 5.91 mmol) in CPME (8 mL) and water (2 mL) was stirred for 5 hours at 100 C under N2. The mixture was diluted with water,extracted with EA(x3), the organic layer was dried, concentrated. The crude product was purified via silica gel chromatography (PE-EA) to give desired compound as yellow solid (140 mg, 30%). ESI MS m/z = 235.3 [M+Hf.

According to the analysis of related databases, 1062368-71-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; OR, Yat, Sun; (434 pag.)WO2017/15449; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1019021-85-2 ,Some common heterocyclic compound, 1019021-85-2, molecular formula is C8H5FN2O2, 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 6-fluoroimidazo[1 ,2-a]pyridine-3-carboxylic acid (13a) (210 mg, 1 .2 mmol) in dichloromethane (8 mL) was added oxalyl chloride (250 muIota, 2.8 mmol) and DMF ( 40 muIota) at 0-10 C. The resulting solution was stirred 30 min at room temperature and concentrated under vacuum. A solution of 3-amino-4-fluoro-N-((1 R,2S)-2-hydroxy-2,3- dihydro-1 H-inden-1 -yl)benzamide (16) (350 mg, 1 .2 mmol) in 3 mL of pyridine was added into the above obtained solid. The resulting solution was stirred 30 minutes at room temperature The above solution was purified by preparative mass trigger LCMS to afford N-(2-fluoro-5-(((1 R,2S)-2-hydroxy-2,3-dihydro-1 H-inden-1 -yl)carbamoyl) phenyl)- 6-fluoroimidazo[1 ,2-a]pyridine-3-carboxamide (F27) as a light yellow solid. 1 H NMR (400MHz, d6-MeOH) delta 9.57 (dd, J = 4.8, 2.4 Hz 1 H), 8.60 (s, 1 H), 8.35 (dd, J = 7.2, 2.4 Hz, 1 H), 7.80-7.85 (m, 2H), 7.65-7.71 (m, 1 H) 7.18-7.37 (m, 5H), 5.54 (d, J = 5.2 Hz, 1 H), 4.65 (td, J = 8.4, 2.0 Hz, 1 H), 3.18 (dd, J = 16, 5.2 Hz,1 H), 2.97(dd, J = 16.4, 2.0 Hz, 1 H). (MS m/z 449.1 (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,1019021-85-2, its application will become more common.

Reference:
Patent; IRM LLC; NOVARTIS PHARMACEUTICALS UK LIMITED; LIANG, Fang; GIBNEY, Michael; YEH, Vince; LI, Xiaolin; MOLTENI, Valentina; SHAW, Duncan; BERMAN, Ashley Mitchell; LEWIS, Sarah; LOREN, Jon; FURMINGER, Vikki; WO2013/33620; (2013); A1;,
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.112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.name: 5-(Trifluoromethyl)pyridin-3-amine

To a solution of 5-(trifluoromethyl)pyridin-3-amine (3 g) in 6N hydrochloric acid (30 mL) was added a solution of sodium nitrite (1.277 g) in water (15 mL) dropwise over 2 minutes at 0 C. The reaction mixture was stirred at 0 C. for 1 hour. To the reaction mixture was added a suspension of tin (II) chloride (8.77 g) in 6N hydrochloric acid (30 mL) dropwise over 3 minutes at 0 C. The reaction mixture was stirred at 0 C. for 28 minutes and at room temperature for 20 hours 9 minutes. To the reaction mixture was added 8N aqueous sodium hydroxide solution (about 68 mL) dropwise at 0 C. The mixture was stirred at 0 C. The mixture was extracted three times with ethyl acetate. The obtained organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated. To the resulting residue was added a seed crystal of the title compound separately synthesized in a similar manner to this step. To the mixture was added a mixture of diisopropylether (2 mL)/n-hexane (30 mL) at room temperature. The suspension was stirred at room temperature. The solid was collected from the suspension by filtration and washed with n-hexane. The solid was dried under reduced pressure at room temperature to give the title compound (2.8464 g) in 87% yield. (0291) 1H-NMR (CDCl3) delta: 3.69 (br s, 2H), 5.49 (br s, 1H), 7.43-7.45 (m, 1H), 8.28-8.30 (m, 1H), 8.34 (d, 1H, J=2.8 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Japan Tobacco Inc.; MIURA, Tomoya; HIRASHIMA, Shintaro; MANABE, Tomoyuki; IIDA, Tetsuya; SAKURAI, Kentaro; (53 pag.)US2019/330193; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7584-08-9, 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 7584-08-9 as follows.

Dissolved 3,5-dimethylpyridine-4-carbonitrile (1.57 g, 11.88 mmol) in DCM (100 mL). Charged with m-Chloroperbenzoic acid (4.10 g, 23.76 mmol). Stirred at room temperature for 16 hours. Washed the reaction mixture with NaHCO3 (100 mL). Washed organic layer with brine and dried over Na2SO4. Filtered and removed solvent. Purified using normal phase chromatography (0-10% MeOH in DCM) to yield 1.57 g of product; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.48 (s, 6H) 8.01 (s, 2H); LCMS (M/Z): 149.2 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7584-08-9, its application will become more common.

Reference:
Patent; Avista Pharma Solutions, Inc.; Speake, Jason D.; (22 pag.)US10239885; (2019); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 29241-65-4, name is 5-Bromo-2-chloronicotinic acid, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To 0.5 L flask charged with 5-Bromo-2-chloronicotinic acid (25.0 g, 106.4 mmol) in MeOH (250 mL) was added H2SO4 (5 mL). The mixture was heated to 60 C., stirred for 1.5 day. LC-MS indicated full conversion of starting material at this time. The reaction was cooled to RT and the volatile components removed in vacuo. The crude residue was dissolved in EtOAc (300 mL), quenched with sat. aqueous Na(HCO3)2 (200 mL). The organic layer was separated, washed with brine, dried over MgSO4 and concentrated to afford the compound, methyl-5-bromo-2-chloronicotinate, as a while solid (quantitative yield). LC-MS (M+H)=250.1.

The synthetic route of 29241-65-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Conn, P. Jeffrey; Lindsley, Craig W.; Stauffer, Shaun R.; Manka, Jason; Jacobs, Jon; Zhou, Ya; Bartolome-Nebreda, Jose Manuel; Macdonald, Gregor James; Conde-Ceide, Susana; Jones, Carrie K.; US2012/172391; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below., Product Details of 63237-88-7

Compound 5 was reported previously.30 For this study, 5 wasre synthesized using a modified synthesis as follows: To a solution of pyrazolo[1,5-a]pyridine-2-carboxylic acid (150 mg, 0.93 mmol)and 4 (230 mg, 0.93 mmol) in anhydrous DMF (5 mL) was added DIPEA (0.33 mL, 1.86 mmol) and HATU (372 mg, 0.98 mmol). After stirring the reaction mixture at room temperature for 16 h the solvent was removed under reduced pressure. The crude mixture was suspended in aqueous 5% NaHCO3 solution and extracted with ethyl acetate (3). The combined organic phases were washed with water and brine and were dried (MgSO4). After removal of solvents under reduced pressure the crude material was purified by flash chromatography (CH2Cl2/MeOH/NH3 aq., 20:1:0.01) to give5 (314 mg, 86%) as a colorless solid. 1H NMR (600 MHz, CDCl3) d8.38-8.34 (m, 1H), 7.61-7.51 (m, 1H), 7.29 (br s, J = 5.2 Hz, 1H),7.18-7.12 (m, 2H), 7.09-7.04 (m, 2H), 6.94 (dd, J = 8.0, 1.4 Hz,1H), 6.88-6.81 (m, 2H), 3.58-3.50 (m, 2H), 2.98-2.87 (m, 4H),2.63 (br s, 4H), 2.51-2.45 (m, 2H), 1.76-1.63 (m, 4H); 13C NMR(150 MHz, CDCl3) d 162.2, 151.5, 148.1, 141.4, 139.0, 128.4,126.4, 123.7, 121.5, 120.0, 119.3, 114.0, 113.6, 98.0, 58.1, 53.9,52.6, 39.1, 27.6, 24.4; ESI-MS m/z 394.2 [M+H]+.

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, 63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid.

Reference:
Article; Stoessel, Anne; Brox, Regine; Purkayastha, Nirupam; Huebner, Harald; Hocke, Carsten; Prante, Olaf; Gmeiner, Peter; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3491 – 3499;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59146-67-7, Adding some certain compound to certain chemical reactions, such as: 59146-67-7, name is 5,6-Dimethylpicolinonitrile,molecular formula is C8H8N2, 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 59146-67-7.

5,6-Dimethylpicolinic acid: 5,6-dimethylpicolinonitrile (example 91b) was refluxed in concentrated HCl (15 mL) overnight. The solvent was evaporated and the solid residue was co-evaporated several times with EtOH. Drying provided 453 mg of 5,6-Dimethylpicolinic acid (80%) as a white solid. MS (M+H, 152.1).

According to the analysis of related databases, 59146-67-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Tachdjian, Catherine; Patron, Andrew P.; Adamski-Werner, Sara L.; Bakir, Farid; Chen, Qing; Darmohusodo, Vincent; Hobson, Stephen Terrence; Li, Xiaodong; Qi, Ming; Rogers, Daniel Harry; Rinnova, Marketa; Servant, Guy; Tang, Xiao-Qing; Zoller, Mark; Wallace, David; Xing, Amy; Gubernator, Klaus; US2005/84506; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 18699-87-1, 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.18699-87-1, name is 2-Methyl-3-nitropyridine, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.

INTERMEDIATE 13 Ethyl 2Z)-2-hydroxy-3-(3-nitropyridin-2-yl)acrylate Sodium metal (400 mg, [17.] 4 mmol) was added portionwise to [ETOH] (50 ml), followed by diethyl oxalate (2.4 [ML,] 17.4 mmol), and stirred at r. t. for 5 min. 2-Methyl-3- nitropyridine [(2. 00] g, 14.6 mmol) was added, giving a deep purple solution that changed over time to red-orange. After stirring for 3 days at r. t. a red precipitate had formed which was collected by filtration and washed with ether (4 x 20 [ML).] The solid residue was suspended in water and the suspension acidified to pH 4 with AcOH. The resulting orange precipitate was collected by filtration, washed with ethanol (10 [ML)] and dried in vacuo to give the title compound (1.17 g, [34%).] [6H] [(CDC13)] 8. [77-8.] 75 [(1H,] m), [8.] [54-8.] 50 [(1H,] m), 7.47-7. 43 (2H, m), 4.48 (2H, q, [J 7.] 1 Hz), 1.49 (3H, t, J7. 1 Hz). LCMS [(ES] RT 3.32 minutes, 239 [(MI]

The chemical industry reduces the impact on the environment during synthesis 18699-87-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CELLTECH R & D LIMITED; WO2004/31188; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 936011-17-5, name is 5-Bromo-2-methoxyisonicotinaldehyde, molecular formula is C7H6BrNO2, 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. Safety of 5-Bromo-2-methoxyisonicotinaldehyde

To a solution of the commercially available 5-bromo-2- methoxyisonicotinaldehyde (5.0 g, 23.2 mmol, leq) in MeOH was added triethylamine (12eq), Pd (dppfjC^ (O. leq) at 70C under 50 psi of CO gas in a steel bomb for 16h. Subsequent reaction work-up and flash column chromatography on silca-gel afforded 1.8 g (39% yield) of the desired compound, methyl 4-formyl-6- methoxynicotinate; LCMS [M + H]+ 196.

With the rapid development of chemical substances, we look forward to future research findings about 936011-17-5.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem