Category: pyridine-derivatives

Application of 1462-86-8, 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.1462-86-8, name is 3-Aminopicolinic acid, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.

Step B. 3-Amino N (cyclohexyloxy)pyridine-2-carboxamide; HATU (2.32 g, 6.10 mmol) was added to a solution of O-cyc1ohexylhydroxylamine (prepared as ref. A. Miyake et al J. Antibiot. 53 (10), 1071-1085, 2000) (0.86 g, 7.50 mmol), DIPEA (1.29 g, 10.0 mmol) and 3-aminopyridine-2-carboxylic acid (0.69 g, 5.00 mmol) in DMF (20 mL) at 0 C. The mixture was stirred overnight at room temperature, diluted with EtOAc (200 mL), washed with H20 (2×10 mL), brine (10 mL) and dried over Na2S04. After evaporation of the solvent, the title compound was purified by MPLC on silica gel using hexane/EtOAc (1: 1) (1.35 g, 100 %) as a white solid. 1H NMR (400 MHz, CDC13) 8 1.30 (m, 2 H), 1.52 (m, 4 H), 1.80 (m, 2 H), 2.06 (m, 2 H), 3.96 (m, 1 H), 5.93 (s, 2 H), 7.00 (dd, J=8.40, 1.37 Hz, 1 H), 7.17 (dd, J=8.40, 4.30 Hz, 1 H), 7.82 (dd, J=4.30, 1.37 Hz, 1 H), 10.12 (s, 1 H).

The chemical industry reduces the impact on the environment during synthesis 1462-86-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AstraZeneca AB; WO2005/115986; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 10201-73-7, Adding some certain compound to certain chemical reactions, such as: 10201-73-7, name is 2-Amino-4-methoxypyridine,molecular formula is C6H8N2O, 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 10201-73-7.

Add in the reaction tube 0.2 mmol of 4-methoxy-2-aminopyridine, 0.2 mmol of beta-nitrostyrene, 10mol% (0.02 mmol) Ce (OTf) 3, 1.5 ml toluene, After the reaction was stirred at 120 C for 10 minutes, the heating and stirring were stopped, the mixture was cooled to room temperature, and the crude product was evaporated under reduced pressure and purified by column chromatography to give the desired product. A mixture of esters (V: V = 5:1), yield 76%. The hydrogen spectrum of the product obtained in this example is shown in Figure 1.The carbon spectrum of the obtained product is shown in Fig. 2.

According to the analysis of related databases, 10201-73-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gannan Normal University; Chen Zhengwang; Ye Min; Zhou Zhonggao; (17 pag.)CN108395399; (2018); A;,
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. 54127-30-9, name is (5,6-Dichloropyridin-3-yl)methanol. A new synthetic method of this compound is introduced below., Safety of (5,6-Dichloropyridin-3-yl)methanol

The intermediate, ethyl (E)-3-{2-[3′-(l-adamantyl)-4′-hydroxyphenyl]-3-chloro-5- pyridinyl}-2-propenoate was prepared as follows.; a) Ethyl (?)-3-(5,6-Dichloro-2-pyridinyl)-2-propenoate.; A reported method(Ognyanov, V. I. et al., J. Med. Chem., 2006, 49, 3719-3742) was used to synthesize 2,3- dichloro-5-formylpyridine. A mixture of 5,6-dichloro-3-pyridinemethanol (1.42 g, 8.00 mmol) and Mn02 (13.9 g, 160 mmol) in 1 : 1 CH2Cl2/hexane (8 mL) was stirred for 1 h, then diluted with 50% EtOAc/hexane (20 mL), and filtered (50% EtOAc/hexane wash). The filtrate was evaporated, and the residue was dried in vacuo for use in the next step.

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, 54127-30-9, (5,6-Dichloropyridin-3-yl)methanol.

Reference:
Patent; WAYNE STATE UNIVERSITY; SANDFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; FONTANA, Joseph, A.; DAWSON, Marcia; XIA, Zebin; WO2011/79305; (2011); A1;,
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. 10592-27-5, name is 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, the common compound, a new synthetic route is introduced below. name: 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine

l,3-Dibromo-5,5-dimethylhydantoin (9.64 g) was added to a mixture of 2,3-dihydro- lH-pyrrolo[2,3-6]pyridine (8.1 g), 4-toluenesulphonic acid monohydrate (1.03 g) and methylene chloride (550 ml) and the resultant mixture was stirred at ambient temperature for 1 hour. The reaction solution was decanted from a black tar. The organic solution was washed with an 0.2M aqueous sodium thiosulphate solution (2 x 250 ml) and with brine, dried over magnesium sulphate and evaporated. There was thus obtained 5-bromo-2,3-dihydro- lH-pyrrolo[2,3-6]pyridine (4.05 g); 1H NMR Spectrum: (DMSOd6) 2.99 (t, 2H), 3.47-3.52 (m, 2H), 6.58 (s, IH), 7.38-7.39 (m, IH), 7.72 (t, IH). Mass Spectrum; M+H+ 199 and 201.

The synthetic route of 10592-27-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/135398; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1214334-70-9, 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. 1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid. A new synthetic method of this compound is introduced below.

Step 3. Synthesis of ethyl 5-bromo-6-methoxypyridine-2-carboxylate (C16). para-Toluenesulfonic acid hydrate (roughly 0.3 g) was added to a solution of 5- bromo-6-methoxypyridine-2-carboxylic acid (C15) (12.2 g, 52.6 mmol) in ethanol (300 mL). The reaction mixture was heated at reflux for 48 hours, then concentrated in vacuo to provide the title product. Yield: 13.5 g, 51 .9 mmol, 99%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1214334-70-9, 5-Bromo-6-methoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; AM ENDE, Christopher William; JOHNSON, Douglas Scott; O’DONNELL, Christopher John; PETTERSSON, Martin Youngjin; SUBRAMANYAM, Chakrapani; WO2011/48525; (2011); 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.136888-26-1, name is 5,6-Dichloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one, molecular formula is C7H4Cl2N2O, molecular weight is 203.0255, as common compound, the synthetic route is as follows.Safety of 5,6-Dichloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

EXAMPLE 51 5,6-Dichloro-3-(2-furoyl)-4-azaoxindole-1-N-t-butyl carboxamide 5,6-Dichloro-3-(2-furoyl)-4-azaoxindole was first prepared according to the procedure of Example 1B, using 5,6-dichloro-4-azaoxindole (763 mg, 3.76 mmol), sodium (0.43 g, 18.8 mmol), ethyl-2-furoate (1.05 g, 7.5 mmol) and ethanol (25 mL). Yield: 0.98 g (88%). The title compound was prepared from 5,6-dichloro-3-(2-furoyl)-4-azaoxindole according to the procedure of Example 1C, using 5,6-dichloro-3-(2-furoyl)-4-azaoxindole (721 mg, 2.43 mmol), triethylamine (1.8 mL, 15.4 mmol), t-butyl isocyanate (1.4 mL, 12.3 mmol) and DMSO (20 mL). The reaction time was 22 hours. The crude product was triturated with methanol and recrystallized from hexane. Yield: 218 mg (23%). Analysis calc’d for C17 H15 Cl2 N3 O4: C 51.53, H 3.82, N 10.60. Found: C 51.70, H 3.81, N 10.57. M.p. 205-206 C. 1 H NMR (DMSO-d6) delta9.37 (br s, 1H), 8.32 (s, 1H), 7.91 (s, 1H), 7.85 (d, J=3.7 Hz, 1H), 6.69 (d, J=3.7 Hz, 1H), 1.38 (s, 9H). IR (KBr disc) 1730, 1620, 1605, 1590, 1555, 1535 cm-1. MS m/e (relative percent) 397(0.5), 395(2), 298(21), 296(33), 230(62), 228(100), 95(40).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,136888-26-1, 5,6-Dichloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc; US5811432; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 18368-63-3, 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 18368-63-3, name is 2-Chloro-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

2-Chloro-6-methylpyridine 4a (5 g, 39.19 mmol, prepared by a known method “Journal of Chemical Research-Part S, 1996, 4, 194-195”),4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis(1,3,2-dioxaborolane)(10.95g, 43.11mmol), (1,5-cyclooctadiene)methoxy ruthenium(I) dimer (779 mg, 1.18 mmol) and 4,4′-di-tert-butyl-2,2′-dipyridine (631 mg, 2.35 mmol) were dissolved in 125 mL of n-hexane, heated to 80 C and stirred for 17 hours. The reaction was stopped, cooled to room temperature and concentrated under reduced pressure.The residue was purified by thin layer chromatography using a developing solvent system B.The title compound 4b (4.9 g, yield: 49.31%) was obtained.

According to the analysis of related databases, 18368-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; Lu Biao; Wang Shenglan; Shen Xiaodong; He Feng; Tao Weikang; (56 pag.)CN109535161; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 80194-68-9, 3-Chloro-5-(trifluoromethyl)picolinic acid, 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: C7H3ClF3NO2, blongs to pyridine-derivatives compound. HPLC of Formula: C7H3ClF3NO2

3-Chloro-5-(trifluoromethyl)picolinic acid (72.3 mg, 320 mupiiotaomicron) was suspended in dichloromethane (5 mL), the suspension was cooled to 0-5C (ice bath) and oxalyl chloride (56.9 mg, 39.3 mu, 448 muiotaetaomicron) as well as dimethylformamide (0.308 M in toluene, 51.9 mu, 16 muiotaetaomicron) were added. The mixture was stirred for 2 h at room temperature. Then, it was concentrated in vacuo (40C, 5 mbar) and dried azeotropically by two cycles of addition of toluene (3 mL) followed by concentration in vacuo to afford 3-chloro-5-(trifluoromethyl)picolinoyl chloride as yellow oil (78 mg, quant.). After that, tert-butyl ((3aS,4R,8R)-4-(5-amino-2-fluorophenyl)-4,7,7- trimethyl-8-oxido-3,3a,4,7-tetrahydro-2H-isothiazolo[l,5-a] [l,4]thiazin-6-yl)carbamate (Int- 16ABp, 80 mg, 188 muiotaetaomicron) was dissolved in dichloromethane (5 mL), the solution cooled to 10C and N,N-diisopropylethylamine (36.5 mg, 49.4 mu, 283 muiotaetaomicron) was added, followed by a solution of 3-chloro-5-(trifluoromethyl)picolinoyl chloride (vide supra, 62 mg, 256 muiotaetaomicron) in dichloro- methane (4 mL). The reaction mixture was stirred for 15 min at 10C. Then, methanol (2 mL) was added, the mixture was stirred for 5 min at room temperature and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 12 g, eluting with ethyl acetate / n-heptane, gradient 25:75 to 100:0) to yield, after drying in vacuo (40C, 5 mbar), the title compound as an off-white solid (100 mg, 84% yield). HPLC (method LCMS_fglm) tR = 1.35 min. MS (ES+) m/z 632.5 [M+H] .

The synthetic route of 80194-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; OBST SANDER, Ulrike; VIFIAN, Walter; WOLTERING, Thomas; (89 pag.)WO2017/25491; (2017); 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 14432-12-3, name is 4-Amino-2-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H5ClN2

To a ice-cooled solution of 4-amino-2-chloro-pyridine (8.09g, 63 mmol, 1eq) in water [(150ML)] was added concentrated 98% HCl whilst maintaining the reaction at [0C A] solution of sodium nitrite (5.65g, [82MMOL,] 1.3eq) in water [(50ML)] was added slowly [AT-10C.] The mixture was stirred at-10C [FOR 40 MIN] and a solution of potassium iodide (12.55g, 75. [6MMOL,] 1.2eq) in water [(50ML)] was added. The resulting mixture was stirred at [0C] overnight. After treatment with [NAOH] 35%, and extraction with ethyl acetate, the organic phases were combined and dried over [NA2SO4.] The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel (eluent : CH2CI2 then [CH2CL2/CH30H] 99/1) to give the title compound as an orange solid (9.5g, 63%) ;’H NMR (300 MHz, CDCl3) [6] : 7.99 (d, [1H),] 7.68 (s, 1H), 7.52 (d, 1H) ; (GC-MS) m/z: 239.

With the rapid development of chemical substances, we look forward to future research findings about 14432-12-3.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/13125; (2004); 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. 19337-97-4, name is trans-3-(3-Pyridyl)acrylic acid. A new synthetic method of this compound is introduced below., SDS of cas: 19337-97-4

Compound 5-3 (2.5 g, 6 mmol) was dissolved in dichloromethane (25 ml), trifluoroacetic acid (5 ml) was added,The solvent was evaporated under reduced pressure for 2 hours to give a brown oil.The reaction mixture was dissolved in dichloromethane (40 ml), and N, N-diisopropylethylamine (2.14 ml, 12 mmol), trans-3 (3-pyridyl) allyl (893 mg, 3 mmol) (2.3 g, 12 mmol), DMAP (145 mg, 0.12 mmol), reacted at room temperature for 8 hours,Saturated ammonium chloride (50 ml) was added and extracted with dichloromethane (50 ml x 3). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure and subjected to column chromatography to give compound 2 ((E) -N- 5- (3- (2-amino-6- (cyclopropylamino) pyrimidin-4-yl) phenol) pentyl) -3- (pyridin-3-yl) acrylamide) (1.7 g, ).

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, 19337-97-4, trans-3-(3-Pyridyl)acrylic acid.

Reference:
Patent; Chinese Academy Of Sciences Guangzhou Bio-pharmaceutical And Health Institute; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; China Pharmaceutical University; Jiang Sheng; Tu Zhengchao; Zhu Jidong; Yao Hequan; Yao Yiwu; Tan Xiaochu; Gu Shoulai; Qiu Yatao; (30 pag.)CN106928192; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem