Day: February 20, 2021

Related Products of 571189-16-7 ,Some common heterocyclic compound, 571189-16-7, molecular formula is C14H20N4O4, 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 2: Synthesis of tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate 10% palladium/carbon catalyst (0.50 g) was added to a solution of tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate (2.85 g, 9.24 mmoL) in methanol (150 mL). The mixed solution was stirred under a hydrogen atmosphere (1 atm) at room temperature for 24 h, and filtered through Celite. The filtrate was concentrated under reduced pressure to obtain tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate (2.12 g, yield: 82.5%).

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. 571189-16-7, tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; WANG, Shulong; CHEN, Kuncheng; LIU, Xijie; HU, Yuandong; LIU, Bo; PENG, Yong; LUO, Hong; HAN, Yongxin; WANG, Shanchun; LIU, Mei; XU, Hongjiang; (38 pag.)EP3434676; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17874-79-2, 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. 17874-79-2, name is 5-(Methoxycarbonyl)picolinic acid, molecular formula is C8H7NO4, 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.

10314] Dimethyl-2,5-pyridinedicarboxylate (960 mg, 4.9mmoles) and CaC12 (2.198 g, 19.7 mmoles) were added to a dried flask. THF (11 mE) and EtOH (12 mE) were added, and the resulting suspension was stirred on ice for 30 minutes. NaI3H4 (465 mg, 12.3 mmoles) was added portion wise with stirring. The reaction was allowed to come to room temperature overnight. Afier 18 h, the reaction was quenched by the dropwise addition of an aqueous solution of NH4C1 (saturated aqueous NH4C1 [20 mE] plus H20 [40 mE]) while stirring on ice. The aqueous layer was extracted with DCM (4×30 mE) and the combined organics were dried over Na2SO4(s) and concentrated under reduced pressure to afford the crude alcohol (678 mg) as a pale yellow solid. The crude alcohol was dissolved in dry DCM (45 mE), after which Dess-Martin periodinane (2.6 g, 6.1 mmoles) was added portion wise while stirring on ice. After 6 h, the reaction was quenched by the dropwise addition of a solution of 5% Na2S2O3 in half saturated NaHCO3 (80 mE). The aqueous layer was extracted with DCM (3×40 mE). The combined organics were dried over Na2SO4(s) and concentrated under reduced pressure to afford the title compound (504 mg, 62%) as a pale yellow solid. ?H NMR (400 MHz, CDC13) oe 10.16 (s, 1H), 9.38 (dd, J=0.5, 2.0 Hz, 1H), 8.49 (dd, J=2.0, 8.0 Hz, 1H), 8.05 (dd, J=0.5, 8.0 Hz, 1H), 4.02 (s, 1H); ?3C NMR (100 MHz, CDC13) oe 192.6, 164.8, 154.9, 151.2, 138.3, 121.1, 52.9; HRMS (El) mlz 165.0415 [calc?d for C8H7N03 (M) 165.042 1]

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 17874-79-2, 5-(Methoxycarbonyl)picolinic acid.

Reference:
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; RAINES, Ronald T.; Vasta, James; (50 pag.)US2016/280701; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 159981-19-8, 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.159981-19-8, name is 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde, molecular formula is C8H6F3NO2, molecular weight is 205.13, as common compound, the synthetic route is as follows.

Resin-bound tetra-alkylcyanoborohydride (9.03 g, 21.2 mmol) was added to a preformed mixture of 7-(benzylthio)-1,2,3,4-tetrahydroisoquinoline (4 g, 14.1 mmol), 6-(2,2,2-trifluoroethoxy)nicotinaldehyde (3.18 g, 15.5 mmol), and glacial acetic acid (3.23 ml, 56.4 mmol) in MeOH (35 ml). The reaction vessel was fitted with a reflux condensor and heated to 40 C. overnight. The reaction mixture was cooled to room temperature, filtered through a fritted funnel, then neutralized by the addition of saturated aqueous NaHCO3 solution. The layers were cut and the aqueous phase extracted with EtOAc¡Á3. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by medium pressure liquid chromatography ?MPLC? (KP-Sil 100 g SNAP column, BIOTAGE system) eluting with 1% MeOH/DCM over 3 CV followed by a gradient of 6-9% MeOH/DCM over 8 CV to give the desired compound. LC/MS (m/z): 445 (M+H)+

The chemical industry reduces the impact on the environment during synthesis 159981-19-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck Sharp & Dohme Corp.; Berger, Richard; Blizzard, Timothy A.; Campbell, Brian T.; Chen, Helen Y.; Debenham, John S.; Dewnani, Sunita V.; Dubois, Byron; Gude, Candido; Guo, Zack Zhiqiang; Harper, Bart; Hu, Zhiyong; Lin, Songnian; Liu, Ping; Wang, Ming; Ujjainwalla, Feroze; Xu, Jiayi; Xu, Libo; Zhang, Rui; (64 pag.)US2018/9796; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 73027-79-9, name is 4,6-Dichloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 73027-79-9

[00240] Step A: 6-Dichloro-4-(2-fluoro-4-iodophenylamino)nicotinic acid:[00241] To a solution of 2-fluoro-4-iodoaniline (11.3 g, 50.3 mmol) in 85 ml anhydrous THF is added LiHMDS (83 ml, 83 mmol, 1M/THF) over a period of 30 min at -78C. It is stirred for another 30 min, then a solution of methyl 4,6-dichloronicotinate (step B, example 9) (5.00 g, 26.2 mmol) in 85 ml THF is added dropwise. After complete addition the mixture is gradually allowed to warm to room temperature and stirred for another 18 hrs. It is quenched with H2O, then 1N HCl is added to (pH = 1) followed by brine. It is extracted using THF and dried with Na2SO4. The solvents are removed and the crude solid is suspended in300 ml of EtOAc. The suspension is heated with stirring at the reflux temperature for 5 min. It is cooled to room temperature and the precipitate is filtered and washed with EtOAc and dried at 50C for 5 h in oil pump vacuo.

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, 73027-79-9, 4,6-Dichloronicotinic acid.

Reference:
Patent; ARDEA BIOSCIENCES, INC.; WO2008/89459; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 625-92-3, 3,5-Dibromopyridine, 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, HPLC of Formula: C5H3Br2N, blongs to pyridine-derivatives compound. HPLC of Formula: C5H3Br2N

[0187] Step 1. 3,5-Dibromoisonicotinaldehyde. Lithium diisopropylamide (507 mmol, 1.2 eq.) was added to 200 mL of dry THF at -78 C under N2. A solution of 3,5-dibromopyridine (100 g, 424 mmol) in 537 mL of dry THF was then added drop-wise over 30 mm. The reaction mixture was stirred at -78 C for 1 h. Ethyl formate (34.4 g, 465 mmol) was added drop-wise and stirred at -78 C for 30 mm, then the reaction mixture was poured into ice-cold saturated aqueous NaHCO3 solution. The mixture was extracted with 3 x 500 mL of EtOAc. The organic layer was concentrated to provide a brown solid, which was filtered through a pad of silica gel (eluted with dichloromethane) to give the title compound as a yellow powder (70 g, 63%).

The synthetic route of 625-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth, W.; BAUMEISTER, Timm, R.; GOSSELIN, Francis; ZAK, Mark; ZHENG, Xiaozhang; WO2013/130935; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 53937-02-3, Adding some certain compound to certain chemical reactions, such as: 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone,molecular formula is C12H11NO2, 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 53937-02-3.

a) 8-(4-Benzyloxy)-2-oxopyridin-1(2H)-yl)-6-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one 8-Bromo-6-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one (0.20 g, 0.68 mmol), 4-benzyloxy pyridinone (0.18 g, 0.89 mmol), and Cs2CO3 (0.24 g, 0.75 mmol) were suspended in DMSO (4.0 mL), and the air was removed under vacuum for 15 min. The system was flushed with Ar and the process repeated. 8-Hydroxyquinoline (30 mg, 0.21 mmol) and copper iodide (0.17 g, 0.89 mmol) were added to the suspension, and the evacuation/Ar flushing process was repeated twice more. The reaction mixture was heated at 130 C. for 18 h under N2. The mixture was cooled, diluted with 5:1 MeOH/NH4OH (10 mL), and the resulting solution was stirred at ambient temperature for 30 min. The reaction was further diluted with CH2Cl2 (75 mL). The solution was filtered through silica gel, and the filtrate was concentrated under reduced pressure. The residue was diluted with CH2Cl2 and washed with brine (3*25 mL). The organic solution was dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. Flash chromatography (12 g ISCO column, (1:1 hexanes/EtOAc)/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 5 column volumes, increased to 50:50 over 20 column volumes and held for 4 column volumes; increased to 0:100 over 10 column volumes) followed by flash chromatography (12 g ISCO column, (1:1 hexanes/EtOAc)/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 5 column volumes, increased to 70:30 over 20 column volumes and held for 4 column volumes; increased to 25:75 over 10 column volumes) followed by trituration in hot EtOH provided the title compound (19 mg, 7%) as an off-white powder: mp 178-181 C.; 1H NMR (500 MHz, DMSO-d6) delta 8.29 (d, J=8.5 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.53 (t, J=5.5 Hz, 1H), 7.49-7.35 (m, 6H), 7.00 (dd, J=8.5, 2.0 Hz, 1H), 6.10 (dd, J=7.5, 2.5 Hz, 1H), 5.97 (d, J=2.5 Hz, 1H), 5.15 (s, 2H), 3.68 (s, 3H), 3.21-3.10 (m, 2H), 3.12 (t, J=6.5 Hz, 2H), 2.08-2.07 (m, 2H); ESI MS m/z 414 [M+H]+; HPLC (Method A) 97.2% (AUC), tR=16.5 min.

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. 53937-02-3, 4-Benzyloxy-2-(1H)-pyridone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2011/3793; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65189-15-3, 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. 65189-15-3, name is 5,6-Dichloronicotinonitrile. A new synthetic method of this compound is introduced below.

Example 3 5-Chloro-2-methylthio-3-pyridinecarbonitrile STR11 5,6-Dichloro-3-pyridinecarbonitrile (1.73 g, 0.01 mol) was dissolved with stirring in dimethyl sulphoxide (25 mL) and sodium methanethiolate (0.77 g, 0.011 mol) added. The reaction mixture was stirred at room temperature for two hours and poured onto ice (100 g). The mixture was extracted with dichloromethane (50 mL), and the organic extract washed with water (100 mL), and brine, and dried over anhydrous sodium sulphate. Evaporation of the solvent under reduced pressure and recrystallisation of the residue from ethyl acetate:hexane gave the desired product (1.3 g, 71%) as a cream solid, MP 147-9 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65189-15-3, 5,6-Dichloronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Kirby; Neil V.; Morrison; Irene M.; Canada; Emily J.; Pieczko; Mary E.; Gustafson; Gary D.; Cooper; David H.; Adamski; Jenifer L.; Mathieson; John T.; Galka; Christopher S.; US6133294; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 175205-82-0, 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. 175205-82-0, name is 2-Bromo-3-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

Step 2: A mixture of 2-bromo-3-(trifluoromethyl)pyridine (50 mg), 2-[4- (ethylsulfonyl)phenyl]-N-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yI)phenyl]acetamide (104 mg), Cs2C03 (87 mg) and PdCl2(dppf)-CH2Cl2 adduct (10 mg) in acetonitrile (1.5 mL) and water (0.5 mL) was sealed in a vessel and heated in the microwave at 100C for 30 mins. The reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was purified by MDAP to afford 2-[4-(ethylsulfonyl)phenyl]-N-{4-[3-(trifluoromethyl)-2- pyridinyl]phenyl}acetamide (32 mg) as a white solid. ‘H-NMR (400 MHz, DMSO-rf6) delta ppm 1.10 (t, J= 7.2 Hz, 3H), 3.28 (q, J= 7.2 Hz, 2H), 3.85 (s, 2H), 7.42 (d, J= 8.4 Hz, 2H), 7.62 (m, 3H), 7.70 (d, J= 8.4 Hz, 2H), 7.86 (d, J= 8.4 Hz, 2H), 8.28 (dd, = 1.2 Hz, 8.0 Hz, 1H), 8.89 (d, J= 4.4 Hz, 1H), 10.46 (s, 1H); 19F-NMR (376 MHz, DMSO-t?) delta ppm -55.98; MS(ES+) m/z 449 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175205-82-0, 2-Bromo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WANG, Yonghui; CAI, Wei; LIU, Qian; MENG, Qinghua; CHENG, Yaobang; YANG, Ting; ZHANG, Guifeng; XIANG, Jianing; WU, Chengde; WO2013/29338; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 106877-33-2, 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.106877-33-2, name is 5-Amino-2-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.

A solution of sodium nitrite (213 mg, 3.08 mmol) in water (620 pL) was slowly added to a suspension of 6-(trifluoromethyl)pyridine-3-amine (500 mg, 3.08 mmol) in cone. HC1 (525 pL) and ice (620 mg) at 0 C. After five minutes of stirring at 0 C a solution of potassium ethyl xanthate (593 mg, 3.70 mmol) in EtOH/water (1/1, 2 mL) was added and the resulting yellow slurry was heated at 50-55 C for 30 minutes. Then the reaction mixture was allowed to cool to rt and was then diluted with water (10 mL) and EtiO (10 mL). The phases were separated and the water phase was extracted with EtiO (2x 10 mL). The combined organics were washed with brine (10 mL) and dried (MgSCri). After filtration and evaporation, the crude material (659 mg) was dissolved in EtOH (8 mL) and potassium hydroxide (735 mg) was added. The resulting mixture was heated at 90 C for two hours and was then allowed to cool to rt. The reaction mixture was then filtered and the filtrate was acidified with citric acid, before being diluted with EtiO. The organic phase was washed with brine and dried (MgSCri). After filtration and evaporation of the solvent, the crude was dried under vacuum at 45 C over night. The title compound (150 mg) was obtained as a yellow crude solid, which was not purified further but used directly in the next step. ‘H NMR (CDCb) S 8.80 (br s, 1H) 7.99 (br d, =8.4 Hz, 1H9 7.66 (br d, =8.4 Hz).

The chemical industry reduces the impact on the environment during synthesis 106877-33-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; RESPIRATORIUS AB (PUBL); DALENCE, Maria; JOHANSSON, Martin; THORNQVIST OLTNER, Viveca; TOFTERED, Joergen; WENSBO, Davis; (49 pag.)WO2020/9653; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1122-71-0, 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. 1122-71-0, name is 6-Methyl-2-pyridinemethanol. A new synthetic method of this compound is introduced below.

Example 45 2-[(6-Methylpyridin-2-yl)methoxy]-4-(2-methylpyrimi din-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine hydrochloride To 2-chloro-4-(2-methylpyrimidin-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine (100 mg), (6-methylpyridin-2-yl)methanol (52 mg), t-Bu-X-Phos (55 mg), and cesium carbonate (398 mg) and Pd2 (dba)3¡¤CHCl3 (34 mg) was added toluene (2.2 mL), and the mixture was degassed, then stirred under Ar atmosphere at 100C for 6 hours. After the reaction mixture was allowed to return to room temperature, diluted with ethyl acetate, filtered through Celite, and the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2-[(6-methylpyridin-2-yl)methoxy]-4-(2-methylpyrimi din-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine (49 mg). Theresulting compound was dissolved in ethyl acetate (2 mL) and 1N HCl/Et2O solution (0.147 mL) was added, then themixture was stirred under ice water cooling for 3 hours. The resulting precipitate was collected by filtration to give thetitle compound (43 mg) as a white powder.[MS (ESI) m/z 333.4 (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,1122-71-0, its application will become more common.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; TSUJI, Takashi; SHIRAI, Masaaki; EP2891656; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem