Category: pyridine-derivatives

Application of 138588-22-4, Adding some certain compound to certain chemical reactions, such as: 138588-22-4, name is 3-(Pyridin-2-yl)-1,2,4-thiadiazol-5-amine,molecular formula is C7H6N4S, 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 138588-22-4.

3-Pyridin-2-yl-[l,2,4]thiadiazo{-5-ylamine (50 mg, 0.28 mmol) was dissolved in 1 mL of anhydrous tetrahydrofuran, to which solution was added p-methoxyphenyl isocyanate (36 muEpsilon, 0.28 mmol). The mixture was stirred at 50 C overnight. Precipitation formed which was filtered and rinsed with methanol to yield a white solid (47,9 mg, 52%). NMR (400 MHz, DMSO-ifc) delta ppm 3.74 (s, 3 H) 6.81 – 7.06 (m, 2 H) 7.32 – 7.46 (m, 2 H) 7.46 – 7.57 (m, 1 H) 7.83 FontWeight=”Bold” FontSize=”10″ 8.06 (m, 1 i n 8.19 i d. ./ 7.S6 Hz, 1 H) 8.60 · 8.90 (m, 1 H) 9.12 (s, 1 I I ) 1 1.49 (s, 1 H); LCMS (M/Z): M+H ” 328.

According to the analysis of related databases, 138588-22-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCYNEXIS INC.; LIU, Hao; SLIGAR, Jessica, Marie; SPEAKE, Jason, Daniel; MOORE, Joseph, A., III; BECK, Brent, Christopher; WO2015/73797; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17570-98-8, 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. 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, 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.

General procedure: 5.1.1 General procedure A (for synthesis of compounds 1-19). To 2-bromoacetylpyridine hydrobromide (1.0 equiv) in anhydrous ethanol (5 mL) was added the corresponding thiourea (1.0 equiv, 0.2 g) and the reaction mixture refluxed for 4 h. After cooling to ambient temperature the reaction mixture was poured into water. The pH of the mixture was adjusted to pH 8 with concentrated aqueous NH4OH and the mixture stirred for 2 h. The precipitate was filtered, washed with ethanol and dried to afford the title compound.

According to the analysis of related databases, 17570-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Meissner, Anja; Boshoff, Helena I.; Vasan, Mahalakshmi; Duckworth, Benjamin P.; Barry III, Clifton E.; Aldrich, Courtney C.; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6385 – 6397;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88569-83-9, 2-Methoxy-6-(methylamino)pyridine, 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: 2-Methoxy-6-(methylamino)pyridine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Methoxy-6-(methylamino)pyridine

Preparation 4 Ethyl 6-iodo-7-methoxy-1-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylate 6-Methoxy-N-methyl-2-pyridinamine (17.24 g, 124 mmol) is dissolved in DMF (160 mL) and cooled to 0 C. followed by the addition of NIS (28 g, 124 mmol, 1 equiv), at a rate which keeps the reaction temperature below 10 C. The reaction is then allowed to warm to room temperature and stirred for 1 h. The reaction is distilled to dryness in vacuo and the residue is dissolved in CH2Cl2 and passed through a silica plug eluding with heptane/EtOAc (9/1) affording 32 g of crude 5-iodo-6-methoxy-N-methyl-2-pyridinamine. The crude 5-iodo-6-methoxy-N-methyl-2-pyridinamine is dissolved in diethyl ethoxymethylenemalonate (32 mL) and the mixture is heated at 140 C. for 2 h, then cooled to room temperature and passed through a silica plug eluding with heptane/EtOAc (19/1, 0/1). The product is then dissolved in Eaton’s reagent (132 mL) and heated at 100 C. for 40 min, cooled to rt and poured into Na2CO3. The basic aqueous layer is then extracted with CH2Cl2 (3*), washed with water, and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography (heptane/EtOAc, 4/1, 1/1, CH2Cl2/MeOH 19/1) the desired product is then triturated with MeOH to afford 7.9 g (16%) of ethyl 6-iodo-7-methoxy-1-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylate. Physical characteristics are as follows: 1H NMR (CDCl3) delta 9.04, 8.52, 4.41, 4.13, 3.91, 1.43; IR (diffuse reflectance) 2491, 2427, 2350, 2282, 2242, 1678, 1632, 1613, 1579, 1384, 1309, 1275, 1227, 1106, 804, cm-1; MS (EI) m/z 388, 344, 343, 317, 316, 185, 159, 86, 84, 51; Anal calcd for C13H13IN2O4: C, 40.23; H, 3.38; N, 7.22. Found: C, 40.20; H, 3.40; N, 7.16.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88569-83-9, 2-Methoxy-6-(methylamino)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Vaillancourt, Valerie A.; Thorarensen, Atli; US2002/19413; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153747-97-8, 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. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate. A new synthetic method of this compound is introduced below.

The compound (R)-N,N-bis(tert-butoxycarbonyl)-3-(1-(2-chloro-3,6-difluorophenyl)ethoxy)-5-(4,4,5 ,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.89 g, 1.46 mmol)Dissolved in DME (10 mL),Then, tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (0.5 g, 1.46 mmol) was added to the reaction mixture.Cesium carbonate (1.43g, 4.38mmol),Water (2mL) andPd(dppf)Cl2.CH2Cl2 (120 mg, 0.15 mmol).After the reaction system was purged with nitrogen (nitrogen) three times,Stir at 100C overnight,Then add ethyl acetate (50 mL)Diluted the reaction solution with water (12 mL).The layers were separated, the aqueous phase was extracted with ethyl acetate (50 mL x 2), and the combined organic phases were washed with saturated brine (25 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The resulting residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether (v/v) = 1/1)The title compound was obtained as a yellow oil (0.69 g, 63%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153747-97-8, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wang Tingjin; (104 pag.)CN104650049; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 66909-38-4, 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.66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine, molecular formula is C6H7ClN2, molecular weight is 142.5862, as common compound, the synthetic route is as follows.

A mixture OF 4-(6-CHLORO-5-METHYL-PYRIMIDIN-4-YLOXY)-PIPERIDINE-1-CARBOXYLIC acid isopropyl ester (1.80 g, 5.74 mmol), palladium acetate (155 mg, 0.69 mmol), biphenyl-3-yl-di-tert-butyl- phosphane (21.5 mg, 0.072 mmol), sodium tert-butoxide (1.38 g, 14.4 mmol), and 6-CHLORO-4-METHYL- pyridin-3-ylamine (838 mg, 5.80 mmol) in 20 mL dioxane was heated in microwave for 1 hour at 120C. Solids were filtered off and mixture was purified by column chromatography (hexane/AcOEt) to give Compound A98 as a tanned solid (702 mg, 29%). H NMR (CDCL3, 400 MHz) 8 1.24-1. 26 (d, 6H), 1.72-1. 81 (M, 2H), 1.95-2. 02 (M, 2H), 2.10 (s, 3H), 2.27 (s, 3H), 3.37-3. 43 (M, 2H), 3.74-3. 77 (M, 2H), 4.90-4. 97 (m, 1H), 5.29-5. 34 (M, 1H), 5.91 (s, 1H), 7.00 (s, 1H), 8.22 (s, 1H), 8.57 (s, 1H). Exact mass calculated for C2OH26CIN503 419.17, found 420.4 (MH+).

The chemical industry reduces the impact on the environment during synthesis 66909-38-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2005/7647; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 112110-07-3, 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

To a mixture of 2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetic acid (34, 0.899 g, 3.21 mmol) in ethyl acetate (20 ml) was added 5-(trifluoromethyl)pyridin-3-amine (10, 0.520 g, 3.21 mmol), triethylamine (1.0 ml) and propylphosphonic anhydride (50 wt % solution in ethyl acetate, 2.51 ml, 4.22 mmol). The mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was suspended in a mixture of ethyl acetate and hexane. The solid precipitate was collected by filtration and washed with hexane. After drying, this provided 1.03 g of compound 46. MS ESI [M+H+]+=425.2.

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; Plexxikon Inc.; Lin, Jack; Ibrahim, Prabha N.; Albers, Aaron; Buell, John; Guo, Zuojun; Pham, Phuongly; Powers, Hannah; Shi, Songyuan; Spevak, Wayne; Wu, Guoxian; Zhang, Jiazhong; Zhang, Ying; (132 pag.)US2017/267660; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 823221-95-0, 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. 823221-95-0, name is 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

Step 2: To a solution of 5-chloro-4-iodo-2-(trifluoromethyl)pyridine (18.2 g, 59.2 mmol) in diethylether (200 mL), at -78 C in a 1L 3 neck RBF, was added n-butyl lithium (1.6 M in hexane, 44.5 mL, 71.1 mmol). The resulting solution was stirred at that temperature for 10 minutes and ethyl-N-Boc-(S)-pyroglutamate (16.75 g, 65.2 mmol) in diethylether (130 mL) was added slowly, and the resulting solution was stirred at that temperature for 1 h. The reaction was stopped by the addition of saturated NH4C1 solution (150 mL) and extracted with EtOAc (2 x 250 mL).The organic layer was washed with water (2 x 150 mL), dried over anhydrous Na2S04 and concentrated to yield ethyl (S)-2-((tert-butoxycarbonyl)amino)-5-(5-chloro-2- (trifluoromethyl)pyridin-4-yl)-5-oxopentanoate which was carried forward to the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,823221-95-0, 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; SHAO, Pengcheng Patrick; KRIKORIAN, Arto, D.; VACHAL, Petr; WO2015/17302; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 102645-33-0, Adding some certain compound to certain chemical reactions, such as: 102645-33-0, name is 2,5-Dichloroisonicotinaldehyde,molecular formula is C6H3Cl2NO, 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 102645-33-0.

(2) To be equipped with mechanical stirring, thermometer,After nitrogen substitution in the three-port reaction flask of the constant pressure dropping funnel,Add the raw materials 4a-1 (200mmol) in sequence,500.0ml tetrahydrofuran, start stirring, and cool down to -85 -90 ,Add 2mol / L n-butyllithium (210mmol) dropwise,The temperature during the dropping is maintained at -85 -90 , and the temperature is kept for 1h after the dropping is completed.A solution of the raw material 2,5-dichloropyridine-4-aldehyde (200 mmol) + 140.0 ml of tetrahydrofuran was added dropwise.After the dropwise addition, the temperature was kept for 0.5h, and the temperature was naturally raised to room temperature for 3h.The reaction solution was poured into 10% aqueous ammonium chloride solution, and extracted with 320.0 ml of toluene,Separate the liquid and extract the aqueous phase once with 320.0 ml of toluene,Combine the organic phases, wash twice with 260.0 ml of water, and separate.The organic phase is dried by adding 12g of anhydrous sodium sulfate and filtered,The organic phase is concentrated (-0.08 -0.09MPa, 55 65 ) to no avail,Add 150.0ml petroleum ether and stir for 0.5h, filter, rinse the filter cake with petroleum ether,Intermediate 4a-2 (150 mmol) was obtained with a yield of 75%.

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. 102645-33-0, 2,5-Dichloroisonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanxi Laite Optoelectric Materials Co., Ltd.; Wu Xingzhi; Xue Zhen; Wang Jinping; (49 pag.)CN111004237; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 700811-29-6, 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 700811-29-6 as follows.

Step 2: 3-(2-chlorophenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-4-carbaldehyde To a solution of 1-(2-chlorophenyl)ethanone (1.08 mL, 8.36 mmol) in AcOH (33 mL) was added 2-chloro-4-hydrazinopyridine (1.20 g, 8.36 mmol). The reaction mixture was allowed to stir at rt for 1 h and was then diluted with water. A white precipitate formed, and the mixture was extracted with EtOAc several times. The organic solutions were combined, washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated.The residue was dissolved in DMF (15 mL) and added to a solution of phosphoryl chloride (1.56 mL, 16.7 mmol) in DMF (13 mL) which had been stirring at rt for 30 min. The reaction mixture was allowed to stir at 80 C. for 18 h and then at rt for 35 h. The mixture was diluted with water and extracted several times with DCM. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-(2-chlorophenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-4-carbaldehyde (1.95 g, 73%). LCMS (AA): m/z=318 (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,700811-29-6, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Chau, Ryan W.; Cullis, Courtney A.; Duffey, Matthew O.; Gipson, Krista E.; Hu, Yongbo; Li, Gang; Sintchak, Michael D.; Vos, Tricia J.; US2013/165464; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 76629-11-3, 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.76629-11-3, name is 3-((6-Chloropyridin-2-yl)amino)propanoic acid, molecular formula is C8H9ClN2O2, molecular weight is 200.6223, as common compound, the synthetic route is as follows.

B) 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one A mixture of N-(6-chloropyridin-2-yl)-beta-alanine (40 g) and Eaton’s Reagent (600 mL) was stirred at 75C for 3 hours. The reaction mixture was poured to ice water and basified to pH = 10 with sodium hydroxide, followed by extraction with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound. MS: [M+H]+ 182.8.

Statistics shows that 76629-11-3 is playing an increasingly important role. we look forward to future research findings about 3-((6-Chloropyridin-2-yl)amino)propanoic acid.

Reference:
Patent; Takeda Pharmaceutical Company Limited; ASANO, Yasutomi; KOJIMA, Takuto; KURASAWA, Osamu; WONG, Tzu-Tshin; HIRATA, Yasuhiro; IWAMURA, Naoki; SAITO, Bunnai; TANAKA, Yuta; ARAI Ryosuke; IMAMURA, Shinichi; YONEMORI, Kazuko; MIYAMOTO, Yasufumi; KITAMURA, Shuji; SANO, Osamu; (222 pag.)EP3287441; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem