Category: pyridine-derivatives

5398-44-7, 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. 5398-44-7, name is 2,6-Dichloroisonicotinic acid, molecular formula is C6H3Cl2NO2, 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.

2,6-Dichloroisonicotinic acid (10 g, 54.6 mmol), N,O-dimethylhydroxylaminehydrochloride (7.99 g, 81.89 mmol), HOBt(8.85 g, 65,52 mmol) and EDCI (12.56 g, 65.52 mmol) were dissolvedin DCM and Et3N (11.38 mL, 81.89 mmol) was added. Afterbeing stirred at room temperature overnight, the reaction mixturewas filtered and the solvent was evaporated in vacuo. The crudeproduct was purified by column chromatography with petroleum/ethyl acetate (4:1) to give intermediate 9 as a white solid (9.97 g,85.45%); 1H NMR (300 MHz, CDCl3) delta 7.50 (s, 2H), 3.58 (s, 3H), 3.37(s, 3H).

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. 5398-44-7, 2,6-Dichloroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shuai, Wen; Li, Xinnan; Li, Wenlong; Xu, Feijie; Lu, Lixue; Yao, Hong; Yang, Limei; Zhu, Huajian; Xu, Shengtao; Zhu, Zheying; Xu, Jinyi; European Journal of Medicinal Chemistry; vol. 197; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

571188-59-5, A common compound: 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate,molecular formula is C14H22N4O2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

In a 2L four-neck round bottom flask,Add 100 g of 2-chloro-4-cyclopentyl-N,N-dimethyl-7H-pyrrole[2,3-d]pyrimidine-6-carboxamide (Formula 2), 104.6 g of 4-(6-aminopyridine- 3-yl) piperazine-1-carboxylic acid tert-butyl ester (formula 1),155.8 g of cesium carbonate, after replacing three times with nitrogen, 800 g of 4-methyl-2-pentanone was added.1.534 g of palladium acetate, 6.38 g of BINAP. After the addition is completed, under a nitrogen atmosphere,The temperature was raised to 90 to 100 C and the reaction was carried out for 3 hours. Cool down to 65 C, add 800g water, 270g n-heptane,10 ml of propylenediamine, cooled to room temperature, filtered, and the filter cake was washed once with 500 g of water.Rinse once with 160g of 4-methyl-2-pentanone/270g of n-heptane mixed solvent.Drying at 60 C gives 4-(6-(7-cyclopentyl-6-(dimethylaminoformyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)aminopyridin-3-yl Piperazine-1-carboxylic acid tert-butyl ester) (Formula 3) 168 g. The yield is 92.2%.Determined by HPLC (area normalization method),4-(6-(7-Cyclopentyl-6-(dimethylaminoformyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)aminopyridin-3-yl)piperidyl The purity of the tert-butyl ester of azine-1-carboxylate was 98.8%.

With the rapid development of chemical substances, we look forward to future research findings about 571188-59-5.

Reference:
Patent; Chongqing San Sheng Industrial Co., Ltd.; Wu Ke; He Wei; Peng Lei; Wang Longlin; Jiang Guangding; Yang Fan; (7 pag.)CN109400612; (2019); A;,
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Pyridine | C5H5N – PubChem

571188-59-5, 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. 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, molecular formula is C14H22N4O2, 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.

In a nitrogen environment at about 25¡À2 C., mix 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbamide and 4-(6-aminopyyrol-3-yl)piperazin-1-carboxyl tert-butylate into tetrahydrofuran THF) added with lithium bis(trimethyl)amine (LiHMDS) and stir for about 1 h to obtain the intermediate 4-[6-[[7-cyclopentyl-6-[(dimethylamino)carbonyl]-7H-pyrrolo[2,3-pyrimidine-2-yl]amino]-3-pyridine]-1-piperazinecarboxyl 1,1-dimethylethylate. Cool the mixture to about 8¡À2 C. and keep the mixture at this temperature while an aqueous hydrogen chloride solution is subsequently added slowly and mixed into the mixture. After that, using a separatory funnel and ethyl acetate as an extracting agent, perform an extraction process in duplicate to acquire the aqueous phase. When the extracted solution is cooled to about 5 C. or lower, slowly add an aqueous sodium hydroxide solution until the pH reaches 12.5. Heat the solution to 25 C. and stir for about 16 h. Next, filter the solution to obtain the solid matter (or filter cake), and rinse the filter cake with DD water until the pH of the rinsing liquid is equal to or lower than 9. Lastly, dry the filter cake at about 55¡À5 C. to yield yellowish brown solids, which are 7-cyclopentyl-N,N-dimethyl-2-{[5-(piperazin-1-yl)pyridin-2-yl]amino}-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, whose molar recovery rate can be 98% or higher, with 98% or higher purity.

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. 571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHUNGHWA CHEMICAL SYNTHESIS & BIOTECH CO. LTD.; Kamani, Satyanarayana; Lu, Tzu-Chiang; Chang, Hsin-Yun; Mai, Chin-Cheng; (30 pag.)US10336763; (2019); B1;,
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. 5470-70-2, name is Methyl 6-methylnicotinate. This compound has unique chemical properties. The synthetic route is as follows. 5470-70-2

Intermediate G:; Methyl (2E)-3-r6-(Hvdroxyrnethyl)pyridin-3-yllacrylic acid The title compound was prepared by the following methodology:LiAIH4, Et2O MnO2, DCM Stage 1 Stage 2 MeO OMe Stage 3K2CO3, H2OTFAA, THF mCPBA, DCM Stage 5 Stage 4 Intermediate G; Stage 1 – Preparation of (6-methylpyridin-3-yl)methanol; To a suspension of lithium aluminium hydride (7.24g, 191mmol) in Et2O (400ml) at -780C was added via cannula over a period of one hour a solution of methyl 6-methylnicotinate (19.62g, 130mmol) in Et2O (20OmL). Once addition was completed, the mixture was stirred for a further 3h. Excess lithium aluminium hydride was quenched by dropwise addition of EtOAc (40 ml). The mixture was then warmed using a water-ice bath, and further quenched with sat NH4CI (50OmL). The ethereal layer was decanted, and EtOAc was added (50OmL). The mixture was stirred vigorously, and the organic layer was again decanted. The extraction procedure was repeated twice (50OmL EtOAc). The combined organic extracts were dried (MgSO4) and concentrated to yield the desired product (13.6g, 85percent). 1H NMR (300MHz, CDCI3) delta: 8.39 (1 H, s), 7.62 (1 H, dd, J=2.1 , 8.1 Hz), 7.14 (1 H, d, J=7.8Hz), 4.68 (2H, s), 2.54 (3H, s).

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, 5470-70-2, Methyl 6-methylnicotinate.

Reference:
Patent; CHROMA THERAPEUTICS LTD.; WO2008/40934; (2008); 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. 98-98-6, name is Picolinic acid. This compound has unique chemical properties. The synthetic route is as follows. 98-98-6

A mixture of picolinic acid (10.0 g, 81.0 mmol, 1 equiv.) and sodium bromide (16.7 g, 162.0 mmol, 2 equiv.) in thionyl chloride (41 mL) was refluxed for 5 h at 80 C. After that, the solvent was removed under the vacuum at 85 C. to afford the brown residue. 80 mL of anhydrous methanol was slowly added into the residue and the mixture was stirred at room temperature for half an hour. The solvent was evaporated, and the residue was taken up in the saturated sodium bicarbonate and extracted with ethyl acetate (three times). The organic layers were combined, washed with saturated brine, dried over anhydrous Na2SO4 and evaporated. The residue was purified by silica gel column; eluting with 33% EtOAc in hexane afforded 4-chloropicolinic acid methyl ester (CYD-1-1) (8.0 g, 64%) as a brown solid; silica gel TLC Rf=0.15 (1:3 EtOAc/hexane); mp 55-56 C.; 1H NMR (600 MHz, CDCl3) delta 8.67 (d, 1H, J=4.8 Hz), 8.16 (d, 1H, J=1.8 Hz), 7.51 (m, 1H), 4.04 (s, 3H).

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, 98-98-6, Picolinic acid.

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; Zhou, Jia; Ding, Chunyong; Cunningham, Kathryn A.; (60 pag.)US9533973; (2017); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

108-48-5, 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. 108-48-5, name is 2,6-Dimethylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 2-methyl quinoline (1 mmol), aryl aldehyde (1 mmol), Ca (OTf)2 (5 mol%) andBu4NPF6 (2 mol%) were heated at 130 oC under neat condition for 4-5 h. After completion of the reaction (monitored by TLC), reaction mixture was brought to roomtemperature, diluted with dichloromethane, absorbed on silica gel and purified by column chromatography using petroleum ether/ethyl acetate to give the desired product.

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 108-48-5, 2,6-Dimethylpyridine.

Reference:
Article; Yaragorla, Srinivasarao; Singh, Garima; Dada, Ravikrishna; Tetrahedron Letters; vol. 56; 43; (2015); p. 5924 – 5929;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

151213-42-2, 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. 151213-42-2, name is (4aR,7aR)-Octahydro-1H-pyrrolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 6-chloro-4-cyclopropyl-7-fluoro-1-oxo-1,4-dihydronaphthalene-2-carboxylic acid 1a (1 g, 3.5 mmol) with N-ethylpiperazine 2c (0.6 g, 5.25mmol) was loaded in a small flask fitted with a micro condenser, placed in the microwave reactor and irradiated for 25 min at 150C under solvent free conditions. The reaction progress was monitored by TLC. Upon completion of the process, addition of hot absolute ethanol (10 mL) to the reaction mixture was followed by filtration. The filtrate was concentrated and stored at room temperature for precipitation. The solid was filtered off and recrystallized from absolute ethanol to give compound 3c.

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 151213-42-2, (4aR,7aR)-Octahydro-1H-pyrrolo[3,4-b]pyridine.

Reference:
Article; Mirzaie; Lari; Vahedi; Hakimi; Russian Journal of General Chemistry; vol. 86; 12; (2016); p. 2865 – 2869; Zh. Obshch. Khim.; vol. 86; 12; (2016); p. 2865 – 2869,5;,
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. 624-28-2, name is 2,5-Dibromopyridine, the common compound, a new synthetic route is introduced below. 624-28-2

To a solution of 2,5-dibromopyridine (10.50 g, 44 mmol) in 210 mL of pyridine was added hydrazine hydrate (80%, 8.85 g, 176.4 mmol), and the mixture was heated to 110 C. and stirred further for 2 hours, then cooled to rt, and concentrated in vacuo. The residue was diluted with DCM (1500 mL). The resulted mixture was washed with aqueous NaOH solution (1 M, 350 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to give the title compound as a gray solid (7.87 g, 94.8%). MS (ESI, pos. ion) m/z: 188.0[M+H]+; 1H NMR (600 MHz, DMSO-d6): delta 8.03 (d, J=2.3 Hz, 1H), 7.67 (s, 1H), 7.59 (dd, J=8.9, 2.5 Hz, 1H), 6.69 (d, J=8.9 Hz, 1H), 4.16 (s, 2H).

Statistics shows that 624-28-2 is playing an increasingly important role. we look forward to future research findings about 2,5-Dibromopyridine.

Reference:
Patent; Calitor Sciences, LLC; Xi, Ning; US2014/134133; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 74115-13-2 as follows., 74115-13-2

[0674] To a solution of 5-bromopyridin-3-ol (LXVII) (174 mg, 1.0 mmol) in DMF (3 mL) was added potassium carbonate (415 mg, 3.0 mmol). The slurry was heated at 90C for 1 h and then cooled to 25C. The (bromomethyl)benzene (LXXI) (171 mg, 1.0 mmol) was added and the mixture was stirred at 25 C overnight. The reaction was worked-up using a saturated sodium bicarbonate and EtOAc extraction. The product was purified by ISCO column (40-100% EtOAc- hexanes). The 3-(benzyloxy)-5-bromopyridine (LXXII) ( 105 mg, 0.398 mmol, 39.8 % yield) was obtained as yellow oil. ESIMS found for Ci2Hi0BrNO mlz 266.1 (M+H).

The chemical industry reduces the impact on the environment during synthesis 74115-13-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (251 pag.)WO2017/24013; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

115473-15-9, 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 115473-15-9, name is 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

The temperature was controlled at 10 to 15 C, 3000 ml of acetonitrile was added to the reaction flask, and 428 g (2.23 mol) of5,6,7,7a-tetrahydrothiophene [3,2-c] 2-pyridone hydrochloride, 1180 g of potassium hydrogencarbonate was slowly added, and then 488 g (2.05 mol) of intermediate 1 was mixed with 400 ml of acetonitrile The reaction mixture was stirred for 18-20 hours. The reaction was monitored by TLC. The solid was filtered off and the solid was removed. The filtrate was concentrated under reduced pressure to distill off the solvent. To the residue was added 1500 ml of ethyl acetate and 1500 ml of n-hexane And the mixture was stirred at 50-60 C for 2 hours. The mixture was filtered through hot filtration and the solid was discarded. The solvent was distilled off from the filtrate under reduced pressure. The residue was dissolved in 1500 ml of acetone, cooled to 5-10 C, and 40% hydrobromic acid 337 ml, The reaction mixture was stirred at 20-25 C for 3 h, cooled to 0-5 C, filtered and rinsed with 200 ml of acetone and dried in vacuo at 40 C for 2 h to give intermediate 2 (5- (alpha-cyclopropylcarbonyl -benzyl) -2-oxo-2,4,5,6,7,7a-hexahydrothieno (3,2-c) pyridine) in about 423 g, 45-60%

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 115473-15-9, 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride.

Reference:
Patent; Beijing Pharmaceutical Technology Development Co., Ltd.; li, jiao; zhao, bo; zhang, lei; (9 pag.)CN105503900; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem