Tag: M.W:100-200

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.105250-17-7, name is (2-Aminopyridin-4-yl)methanol, molecular formula is C6H8N2O, molecular weight is 124.14, as common compound, the synthetic route is as follows.name: (2-Aminopyridin-4-yl)methanol

Intermediate C: 1 -(4-((2-aminopyridin-4-yl)methoxy)naphthalen-1 -yl)-3-(3-ferf-butyl-1 -p- tolyl-1 H-pyrazol-5-yl)urea To a solution of 4-nitronaphthol (5.17 g, 27.3 mmol), triphenylphosphine (10.75 g, 41 .0 mmol) and 2-aminopyridine-4-methanol (5.09g, 41.0 mmol) in THF (50 mL) at -15°C was added dropwise DIAD (8.07 mL, 41.0 mmol) and the mixture then allowed to warm to RT and stirred overnight. The volatiles were removed in vacuo and the residue was triturated with EtOAc (150 mL), and the crude product was collected by filtration and washed with EtOAc (100 mL). A second trituration with MeOH (100 mL) gave 2-amino-4-((4-nitronaphthalen-1 – yloxy)methyl)pyridine (4.54 g, 56percent) as a yellow solid: m/z 296 (M+H)+ (ES+).A solution of 2-amino-4-((4-nitronaphthalen-1 -yloxy)methyl)pyridine (4.50 g, 15.24 mmol) in MeOH (200 mL) and AcOH (200 mL) was passed through a Thales H-cube (2.0 mLmin”1, 40 °C, 55 mm 10percent Pt/C Cat-Cart, full hydrogen mode) and the volatiles were removed in vacuo. The crude product was subjected to SCX capture and release and the solvent was removed in vacuo to give 2-amino-4-((4-aminonaphthalen-1 -yloxy)methyl)pyridine, (3.82g, 94percent) as a purple solid: m/z 266 (M+H)+ (ES+). A solution of CDI (4.18 g, 25.8 mmol) in DCM (15 mL) was added dropwise under nitrogen to a solution of Intermediate A (5.91 g, 25.8 mmol) in DCM (15 mL) over 40 min. The resulting solution was stirred at RT for 1 hr and was then added dropwise under nitrogen to a solution of 2-amino-4-((4-aminonaphthalen-1 -yloxy)methyl)pyridine (3.80 g, 12.9 mmol) in DCM and the mixture was stirred overnight. The volatiles were removed in vacuo.and the residue was purified by flash column chromatography (Si02, 120 g, MeOH in DCM, 0-6percent, gradient elution) to give the tite compound, Intermediate C, as an off white solid (4.27 g, 63percent): m/z 521 (M+H)+ (ES+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105250-17-7, (2-Aminopyridin-4-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; RESPIVERT LIMITED; KING-UNDERWOOD, John; ITO, Kazuhiro; STRONG, Peter; RAPEPORT, William Garth; CHARRON, Catherine Elisabeth; MURRAY, Peter John; WILLIAMS, Jonathan Gareth; ONIONS, Stuart Thomas; WO2011/124923; (2011); A2;,
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. 770-08-1, name is 5-Ethylpicolinic acid. A new synthetic method of this compound is introduced below., Product Details of 770-08-1

a. Benzyl (5-Ethyl-2-pyridyl)carbamate Diphenylphosphoryl azide (4.04 g., 14.7 mmoles) was added to a solution of 5-ethylpyridine-2-carboxylic acid (2.22 g., 14.7 mmoles), triethylamine (1.485 g., 14.7 mmoles), and benzyl alcohol (1.75 g., 16.17 mmoles) in 1,4-dioxane (23.5 ml.), and the mixture heated under reflux for one hour. The 1,4-dioxane was removed under reduced pressure. A solution of the residue in toluene was washed successively with water, aqueous sodium bicarbonate, and brine, and was then dried over sodium sulfate. The toluene was removed and the residue recrystallized from 2-propanol to give benzyl (5-ethyl-2-pyridyl)carbamate (1.9 g., 50.5%), m.p. 125-127. An analytical sample had m.p. 127-130. Anal. Calcd for C15 H16 N2 O2: C, 70.29; H, 6.29; N, 10.93. Found: C, 70.01; H, 6.32; N, 10.72.

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, 770-08-1, 5-Ethylpicolinic acid.

Reference:
Patent; Bristol-Myers Company; US4122274; (1978); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 105250-17-7, 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. 105250-17-7, name is (2-Aminopyridin-4-yl)methanol, molecular formula is C6H8N2O, 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.

Preparation of 4-({rtgrt-butvirdimethyl)silylloxy}methvDpyridin-2-amineA solution of (2-aminopyridin-4-yl)methanol (5.0 g, 40 mmol), tert- butyldimethylsilyl chloride (6.07 g, 40 mmol), N-ethyl-N-isopropylpropan-2-amine (7.0 mL, 40 mmol) and ??N-dimethylpyridin-4-amine (0.49 g, 4 mmol) in dichloromethane (50 mL) was stirred 2 days at ambient temperature under nitrogen. The resulting reaction mixture was washed in sequence with aqueous sodium hydroxide (1 N), water and brine. It was then dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel using 50 percent ethyl acetate in hexane to yield pure title compound (5.47 g).1H NMR (300 MHz, CD3CN) ? 7.75 (m, IH), 6.39 -6.48 (m, 2H), 4.70 (bs, IH), 4. 50 (s, 2H), 0.83 (s, 9H) and 0.03 ppm (s, 6H); ES-MS m/z 239.3 [M+H]+, HPLC RT (min) 2.35.

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 105250-17-7, (2-Aminopyridin-4-yl)methanol.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/133006; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 956010-88-1, 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. 956010-88-1, name is 1H-Pyrazolo[3,4-b]pyridine-3-carbonitrile, molecular formula is C7H4N4, 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.

The above-obtained 3-chloromethyl)-2-fluoropyridine and 5.44 g3-cyano-1H-pyrazolo[3,4-b]pyridine was dissolved in 110 mL of DMF, 10.42 g of K2CO3 was added, N2 was protected, and the mixture was stirred at room temperature for 30 min, and then reacted overnight at 40 C. under the protection of N2. The reaction was monitored by TLC and the reaction was complete. After adding 200 mL of water, the mixture was stirred, extracted with ethyl acetate (110 mL*3), washed with saturated brine (60 mL), dried over anhydrous MgSO4, suction filtered, and the solvent was distilled off under reduced pressure. Column chromatography yielded 7.54 as a white solid. g, yield 78.9%.

According to the analysis of related databases, 956010-88-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Li Song; Zheng Zhibing; Lin Feng; Gong Zehui; Lu Xinqiang; Zhou Xinbo; Zhong Wu; Xiao Junhai; Xie Yunde; Li Xingzhou; Wang Xiaokui; (24 pag.)CN107964011; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5975-12-2 , The common heterocyclic compound, 5975-12-2, name is 2,4-Dichloro-3-nitropyridine, molecular formula is C5H2Cl2N2O2, 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.

b) Synthesis of 4-chloro-3-nitro-pyridin-2-ol 2,4-dichloro-3-nitro-pyridine (4.01 g, 20.8 mmol) and cesium acetate (8.0 g, 41.6 mmol) were dissolved in anhydrous N,N-dimethyl formamide (104 ml) under nitrogen atmosphere, and the reaction mixture was heated to 800 and stirred for 18 hours. The reaction mixture was cooled to room temperature the reaction was quenched by adding water. The organic layer was extracted with ethyl acetate, and the combined organic layer was washed with water and saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure to obtain pale-yellow solid (1.69 g, 47%). 1H-NMR (DMSO-d6, 300 MHz); delta=8.24 (d, J=5.7 Hz, 1H), 7.09 (d, J=5.7 Hz, 1H).

The synthetic route of 5975-12-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ahn, Sung Oh; Park, Chan Hee; Im, Jun Hwan; Lee, Soon Ok; Lee, Kyoung June; Cho, Seong Wook; Ko, Kwang Seok; Han, Sun Young; Lee, Won Il; US2011/28467; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 81719-53-1, 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 81719-53-1 as follows.

To 4-hydrazinocarbonylpiperidine-1-carboxylic acid tert-butyl ester (500 mg) were added 3,5-dichloropyridine-2-carboxylic acid (475 mg), 1-hydroxybenzotriazole (420 mg),1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide.hydrochloride (590 mg), triethylamine (575 muL) and chloroform (10 mL) and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography (chloroform:methanol)to give 4-[N’-(3,5-dichloropyridine-2-carbonyl)hydrazinocarbonyl]piperidine-1-carboxylic acid tert-butyl ester (525 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,81719-53-1, its application will become more common.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 633328-33-3, 3-Bromo-1H-pyrazolo[4,3-b]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, SDS of cas: 633328-33-3, blongs to pyridine-derivatives compound. SDS of cas: 633328-33-3

To a stirred solution of 3-bromo-1 H-pyrazolo[4,3-b]pyridine (500 mg, 2.52 mmol) in DMF, NaH (60%) (201 mg, 5.04 mmol) was added at 0C and it was stirred for 15min. Then, 1 -bromo-2-methoxyethane (420 mg, 3.02 mmol) was added and the reaction mixture was stirred at rt for 2h. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2S04, and it was concentrated under reduced pressure. The crude compound was purified by flash column chromatography on 230-400 silica using 45% EtOAc in pet ether as an eluent to afford the title compound (430 mg, 66%) as a gummy solid.LC-MS (method 24): R, = 2.63 min; m/z = 258.01 (M+2H+),

At the same time, in my other blogs, there are other synthetic methods of this type of compound,633328-33-3, 3-Bromo-1H-pyrazolo[4,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ORYZON GENOMICS, S.A.; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; SALAS SOLANA, Jorge; (103 pag.)WO2019/110663; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1594-57-6, 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. 1594-57-6, name is N-Hydroxyisonicotinimidamide, molecular formula is C6H7N3O, 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.

Zn(CH3COO)2·2H2O (21.9 mg, 0.1 mmol) and pyridine-4-amidoxime (27.4 mg, 0.2 mmol) were dissolved in a 30 mL mixture of methanol and dimethylformamide (2:1). The reaction mixture was boiled and stirred for ?20 min, filtered off and then slowly cooled to room temperature, giving yellow crystals. Yield: ?23%. Anal. Calc. for C16H20N6O6Zn: C, 41.98; H, 4.40; N, 18.35. Found: C, 41.25; H, 4.33; N, 18.09%. UV-Vis (CH3OH) [lambdamax, nm (epsilon, dm3 M-1 cm-1)]: 210 (27 619), 273 (9115). IR (cm-1): 3456 (w), 1648 (m), 1614 (v.s), 1586 (v.s), 1550 (s), 1424 (s), 1380 (v.s), 1333 (s), 1223 (m), 1073 (m), 1028 (m), 955 (m), 939 (m), 839 (s), 676 (m), 453 (w), 411 (w).

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 1594-57-6, N-Hydroxyisonicotinimidamide.

Reference:
Article; Coropceanu, Eduard B.; Croitor, Lilia; Siminel, Anatolii V.; Fonari, Marina S.; Polyhedron; vol. 75; (2014); p. 73 – 80;,
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. 4214-73-7, name is 2-Amino-5-cyanopyridine. A new synthetic method of this compound is introduced below., COA of Formula: C6H5N3

A solution of 6-aminonicotinonitrile (10 g, 80 mmol) in acetonitrile (300 mL) was treated with a 50% aqueous solution of 2-chloroacetaldehyde (26.4 mL, 210 mmol). The mixture was stirred and heated to reflux. After 6 hours, the mixture was cooled to room temperature. The mixture was concentrated to low bulk (approx. 100 mL), treated with saturated aqueous sodium hydrogencarbonate solution to neutral pH, and then extracted with dichloromethane (2 x 300 mL). The organic layer was dried (MgS04) and evaporated and the residue was stirred with diethyl ether (200 mL), filtered and dried in vacuum to give the title compound (22.54 g, 94%) as a pale brown solid.LRMS (m/z): 144 (M+1)+.1H-NMR delta (CDCI3): 7.29 (dd, 1 H), 7.71 (d, 1 H), 7.73 (d, 1 H), 7.80 (d, 1 H), 8.61- 8.62 (m, 1 H).

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, 4214-73-7, 2-Amino-5-cyanopyridine.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; BACH TANA, Jordi; PAGES SANTACANA, Lluis Miquel; TALTAVULL MOLL, Joan; CATURLA JAVALOYES, Juan Francisco; MATASSA, Victor Giulio; WO2011/76419; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 107504-08-5 ,Some common heterocyclic compound, 107504-08-5, molecular formula is C6H4FNO2, 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.

A mixture of 14 (500 mg, 4 mmol) and LiAIH4(202 mg, 5 mmol) in THF (10 mL) was degassed and purged with N2for 3 times, and then the mixture was stirred at 0 C for 12 h under N2atmosphere. The reaction mixture was quenched by saturated sodium potassium tartrate (0.8 mL) at 15 C, and then filtered. The mixture was diluted with H20 (5 mL) and extracted with EtOAc (5 mL x 3). The combined organic layer was washed with brine (5 mL x 2), dried over Na2S04, filtered and concentrated under reduced pressure to give 15 (236 mg, 52%) as a yellow solid.1H NMR (400 MHz, DMSO-d6) 8.43 (d, J – 2.8 Hz, 1 H), 7.45-7.41 (m, 1 H), 7.31-7.27 (m, 1 H), 4.76 (s, 2H). A mixture of 15 (1 g, 8 mmol), DCC (3 g, 16 mmol), DMAP (96 mg, 786 umol) and A/-BOC-(S)-valine (2 g, 9 mmol) in DCM (5 mL) was degassed and purged with N2for 3 times, and then the mixture was stirred at 25 “C for 12 h under N2atmosphere. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Si02, PE/EtOAc = 5:1) to give 16 (1 .3 g, 51 %) as a yellow liquid.1H N R (400 MHz, DMSO-de) 8.55 (s, 1 H), 7.71-7.83 (m, 1 H), 7.54-7.51 (m, 1 H), 7.25 (d, J = 8.0 Hz, 1 H), 5.22-5.13 (m, 2H), 3.91 (t, J = 7.2 Hz, 1 H), 2.06-2.02 (m, 1 H), 1.38 (s, 9H), 0.87 (d, J – 6.4 Hz, 6H).

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. 107504-08-5, 5-Fluoro-2-picolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; CARTER, David Scott; HALLADAY, Jason S.; JACOBS, Robert T.; LIU, Yang; PLATTNER, Jacob J.; ZHANG, Yong-Kang; WITTY, Michael John; (149 pag.)WO2017/195069; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem