Pyridine-derivatives

Electric Literature of 6628-77-9, Adding some certain compound to certain chemical reactions, such as: 6628-77-9, name is 5-Amino-2-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 6628-77-9.

a 3-Amino-2-bromo-6-methoxypyridine Sodium acetate (1.6 g) was added to a solution of 5-amino-2-methoxypyridine (2.5 g) in acetic acid (15 ml). To the resulting solution bromine (3.0 g) was added dropwise, and the mixture was stirred for 20 min., and then added to a solution of sodium hydroxide (10 g) in water (100 ml). The product was extracted with ethyl acetate (50 ml), dried (anhydrous magnesium sulfate), and concentrated in vacuo. The product was purified over a silica gel column (ethyl acetate/hexane, 1:4) to give 2.7 g of the title compound, suitable for use in the next reaction.

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. 6628-77-9, 5-Amino-2-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US5366972; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1101120-37-9, 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. 1101120-37-9, name is Pyrazolo[1,5-a]pyridin-5-amine. A new synthetic method of this compound is introduced below.

A solution of the appropriate carboxylic acid (1 eq.) and the appropriate amine (1.1-1.5 eq.) in pyridine (about 0.1M) was heated to 60 C., and T3P (50% in ethyl acetate, 15 eq.) was added dropwise. Alternatively, T3P was added at RT and the mixture was then stirred at RT or heatedto 60 to 90 C. Afier 1-20 h, the reaction mixture was cooled to RT, and water and ethyl acetate were added. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with aqueous buffer solution (pH=5), with saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. The crude product was then optionally purified either by normal phase chromatography (mobile phase: cyclohexane/ethyl acetate mixtures or dichloromethane/methanol mixtures) or by preparative RP-HPLC (water/acetonitrile gradient or water/methanol gradient).; 193 mg (583 jtmol.) of 2-{5-[(benzyloxy)carbo- nyl]-4-hydroxy-2-oxopyridin- 1 (2H)-yl}butanoic acid (race- mate) and 116 mg (874 jtmol. 1.5 eq.) of pyrazol[i,5-a] pyridine-5-amine were reacted according to General Method SD. Yield: 233 mg (purity 94%, 84% of theory)j0872] LC/MS [Method 1]: R=0.9S mm; MS (ESIpos):mlz=447 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1101120-37-9, Pyrazolo[1,5-a]pyridin-5-amine, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; ROeHRIG, Susanne; HILLISCH, Alexander; STRASSBURGER, Julia; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; BUCHMUeLLER, Anja; GERDES, Christoph; SCHAeFER, Martina; TELLER, Henrik; JIMENEZ NUNEZ, Eloisa; SCHIROK, Hartmut; KLAR, Juergen; (66 pag.)US2016/272637; (2016); 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. 174669-74-0, name is 2-Fluoropyridin-3-ol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Fluoropyridin-3-ol

Step-1: Preparation of 6-bromo-2-fluoropyridin-3-ol [0175] To a solution of 2-fluoropyridin-3-ol (1 g, 8.842 mmol) and sodium acetate (0.72 g, 8.842 mmol) in acetic acid (10 mL) was added bromine (0.23 mL, 8.842 mmol) at 0 C and the reaction mixture was stirred at room temperature for 4 h. The solution was poured into ice, pH was adjusted to 6 using 2N sodium hydroxide solution and extracted with ethyl acetate (50 mL x 2). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford the crude product, which was purified by silica gel column chromatography (10% ethyl acetate/hexane) to obtain the title compound 6-bromo-2- fluoropyridin-3-ol (0.5 g, 30% yield) as a colorless liquid. Calculated (M+H): 193; Found (M+l): 193.9

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, 174669-74-0, 2-Fluoropyridin-3-ol.

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; MENNITI, Frank S.; WO2015/48507; (2015); 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 152460-10-1, name is N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C16H15N5

1,4-Dioxane (75 ml) and thionyl chloride (45.5 ml) were added to p-toluic acid (25 g) and the mixture was heated at 60C for 12 hours. The resulting mass was distilled under vacuum at 50C to produce an oily mass. The resulting oil was slowly added to a stirred suspension of (45.8 g), potassium carbonate (63 g), tetrahydrofuran (238 ml) and N-(5- Amino-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine at 0C. The resulting mass was stirred for 3 hours at 25C and followed by quenching in a mixture of water (700 ml) and ethyl acetate (92 ml). The resulting mixture was stirred for 2 hours at 25 C and filtered the solid. The solid was washed with water (400 ml) and ethyl acetate (200 ml), and dried in an air oven at 65C for 8 to 10 hours to give 47.5 g of 4-methyl-N-[4-methyl-3-[[4-(3- pyridinyl)-2-pyrimidinyl]amino] phenyl] benzamide (Purity by HPLC: 99.6%).

With the rapid development of chemical substances, we look forward to future research findings about 152460-10-1.

Reference:
Patent; ACTAVIS GROUP PTC EHF; KHUNT, Mayur, Devjibhai; PATIL, Nilesh, Sudhir; PAGIRE, Haushabhau, Shivaji; PRADHAN, Nitin, Sharadchandra; WO2011/95835; (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.571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, molecular formula is C14H22N4O2, molecular weight is 278.35, as common compound, the synthetic route is as follows.Application In Synthesis of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate

To the three-necked flask added tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate (30.62 g, 110 mmol), 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (29.28 g, 100 mmol), sodium tert-butoxide (14.42 g, 150 mmol) and dimethylacetamide (293 mL), stirred evenly, cooled to 0 ~ 5 C vacuum switching nitrogen protection, BrettPhos Pd G3 (418 mg, 0.5 mmol) was added, and after the addition was completed, the temperature was raised to 105 to 110 C for 6 to 8 hours. After end of the reaction was cooled to room temperature, a saturated aqueous ammonium chloride solution (293 mL) was added to quench the reaction. The aqueous phase was extracted 3 times with ethyl acetate (146 mL). The organic phase was washed once with saturated brine (146 mL). dry over sodium sulfate, filter through celite, concentrate and add ethanol and petroleum ether. slurry, filter to separate the solid, drying in vacuo to give the compound tert-butyl 4-(6-((7-cyclopentyl-6-(dimethylaminoformyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate (41.17 g, 77%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Hangzhou Kechao Biological Technology Co., Ltd.; Yu Wei; Zhang Yiping; (21 pag.)CN108586356; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1480-87-1 ,Some common heterocyclic compound, 1480-87-1, molecular formula is C5H3FN2O2, 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 0.3 g (2.44 mmol) 1(1R)-1-(3-methylisoxazol-5-yl)ethanol in THF 2.45 mL (1 M in THF; 2.45 mmol) LiHMDS is added drop wise. After 30 minutes of stirring 0.3 g (2.04 mmol) 2-fluoro-3-nitro-pyridine is added. The mixture is stirred over night. The mixture is diluted with 1 N HCl and water and neutralized with NH3. EtOAc is added and the organic layer is separated, washed with brine, dried and evaporated to furnish 3-methyl-5-[(1R)-1-[(3-nitro-2-pyridyl)oxy]ethyl]isoxazole. A mixture of 0.5 g (2.09 mmol) 3-methyl-5-[(1R)-1-[(3-nitro-2-pyridyl)oxy]ethyl]isoxazole and acetone are cooled to 5 C. and 87 ml (17.4 mmol) of titanium(III)chloride 20% in water and 24 ml (96 mmol) of a 4M solution of NH4Cl in water are added. The mixture is warmed to RT and stirred over night diluted with EtOAc and water. The organic layer is separated and the aqueous layer is extracted with EtOAc. The combined organic layers are washed with brine, dried and evaporated. The residue is purified by FC (DCM/MeOH 95:5). Yield: 0.3 g (72%), ESI-MS: m/z=220 (M+H)+, Rt(HPLC): 0.41 min (HPLC-G)

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. 1480-87-1, 2-Fluoro-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BLUM, Andreas; GOTTSCHLING, Dirk; HECKEL, Armin; HEHN, Joerg P.; SCHMID, Bernhard; WIEDENMAYER, Dieter; US2015/5278; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 128071-98-7 ,Some common heterocyclic compound, 128071-98-7, molecular formula is C5H3BrFN, 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.

Synthesis of Compound 35.1 [0308] To a solution of 4-bromo-2-fluoropyridine (5.0 g, 28.6 mmol, 1.0 eq) in THF (50 mL) were added 2, 2′-oxydiethanol (9.1 g, 85.8 mmol, 3.0 eq) and t-BuOK (3.8 g, 34.3 mmol, 1.2 eq). After stirred at room temperature for 12 h, the reaction mixture was diluted with water (20 mL) and extracted with EA (20 mL x 3). The combined organic layers were washed with brine (20 mL x 5), dried over anhydrous Na2S04 , and concentrated under reduced pressure. The residue was purified by chromatography column (PE : EA = 3 : 1) to give 35.1 (6.4 g, yield: 86%) as a yellow oil; ESI-MS (M+H)+: 262.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,128071-98-7, its application will become more common.

Reference:
Patent; BIOGEN IDEC MA INC.; JENKINS, Tracy; VESSELS, Jeffery; WO2014/143672; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 109-09-1 ,Some common heterocyclic compound, 109-09-1, molecular formula is C5H4ClN, 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.

General procedure: A mixture of 2-chloro-5-methyl-benzimidazole (10.2 g, 61.2 mmol) and hydrazine monohydrate (59 mL, 1.22 mol) was stirred at 100 C overnight. After being cooled to ambient temperature, to the reaction mixture was added to water (60 mL). After stirring under ice cooling, the resulting precipitates were collected by filtration. The precipitates were washed with water 3 times, and then dried in vacuo to give 2-hydrazino-5-methyl-benzimidazole (8.4 g, 84.6%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109-09-1, its application will become more common.

Reference:
Article; Nakao, Syuhei; Mabuchi, Miyuki; Shimizu, Tadashi; Itoh, Yoshihiro; Takeuchi, Yuko; Ueda, Masahiro; Mizuno, Hiroaki; Shigi, Naoko; Ohshio, Ikumi; Jinguji, Kentaro; Ueda, Yuko; Yamamoto, Masatatsu; Furukawa, Tatsuhiko; Aoki, Shunji; Tsujikawa, Kazutake; Tanaka, Akito; Bioorganic and Medicinal Chemistry Letters; vol. 24; 4; (2014); p. 1071 – 1074;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 73781-91-6, Adding some certain compound to certain chemical reactions, such as: 73781-91-6, name is Methyl 6-chloronicotinate,molecular formula is C7H6ClNO2, 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 73781-91-6.

f) 6-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]-triazol-4-ylmethoxy)-nicotinic acid methyl ester A solution of (3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-yl)-methanol (158 mg, 0.83 mmol) in THF (2.4 mL) was added dropwise at 0 C. to a suspension of NaH (60% in oil, 40 mg, 0.91 mmol) in THF (1.2 mL) and the reaction mixture was then stirred at room temperature for 30 min. Then a solution of methyl 6-chloronicotinate (157 mg, 0.91 mmol) in THF (2.4 mL) was added dropwise at 0 C. and the reaction mixture stirred at room temperature for 18 h. The mixture was then poured into water extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (209 mg, 77%) as a white solid. MS: m/e=326.1 [M+H]+.

According to the analysis of related databases, 73781-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hernandez, Maria-Clemencia; Lucas, Matthew C.; Thomas, Andrew; US2012/115844; (2012); 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. 84703-18-4, name is 5-Bromo-2-chloro-6-methylnicotinonitrile, molecular formula is C7H4BrClN2, 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. Recommanded Product: 84703-18-4

Step 1: 5-bromo-2-chloro-6-methylnicotinaldehyde (119b) To a solution of 5-bromo-2-chloro-6-methylnicotinonitrile (0.20 g, 0.86 mmol) in DCM (200 mL) was successively added DIBAL (0.86 mL, 1.30 mmol) at -78 C. under N2. The reaction mixture was stirred at room temperature for 2 h. the mixture was diluted with water and EtOAc. The organic layer was separated and the aqueous layer extracted with EtOAc. The residue was purified by column chromatography on silica gel to give 119b (20.0 g, 60.4%) as a yellow solid. LC-MS (ESI): m/z=233.9 [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 84703-18-4.

Reference:
Patent; Fronthera U.S. Pharmaceuticals LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; LI, Yao; (169 pag.)US2019/367515; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem