Tag: M.W:100-200

Synthetic Route of 58481-17-7, 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.58481-17-7, name is Methyl 2-(hydroxymethyl)isonicotinate, molecular formula is C8H9NO3, molecular weight is 167.16, as common compound, the synthetic route is as follows.

Methyl 2-{hydroxymethyl)isontcotinate (3,17mmol, 0.53Og) and triethylamine(9.51 mmol, 1.322mL, 0.963g) were stirred in dichloromethane (2OmL) at O0C.Methanesulfony chloride (4.7betammol, 0.368mL. 0.545g) was added dropwise and the reaction stirred at room temperature for 1 hour. The reaction mixture was washed with water, dried over sodium sulfate and concentrated under vacuum to afford the title compound (688mg). MS (ES.) m/z 246.4 p+Hf

The chemical industry reduces the impact on the environment during synthesis 58481-17-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; N.V. ORGANON; PHARMACOPEIA, LLC; COOKE, Andrew, John; BENNETT, David, Jonathan; EDWARDS, Andrew Stanley; ROUGHTON, Andrew Laird; NEAGU, Irina; CHAN, Jui-Hsiang; HO, Koc-Kan; ANSARI, Nasrin; MORRIS, Michelle Lee; RONG, Yajing; OHLMEYER, Michael; WO2010/25179; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18368-59-7, 3-Bromo-4-methylpyridin-2-ol, 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, 18368-59-7, blongs to pyridine-derivatives compound. Formula: C6H6BrNO

Synthesis of interaiediate V-c : 3 -Bromo-2-methoxy-4-methyl -pyridineA solution of 3-bromo-4-methyl-2-pyridone V-b (2.20 g, 11.7 mmol), in DCM (80 mL) was treated with Mel (7.29 mL, 117 mmol) and Ag2C03 (6.47 g, 23.5 mmol). The flask was stoppered and stirred under argon for 6 days. The mixture was filtered and purified by column chromatography (Si02; 10% EtOAc in cyclohexane) to afford the desired product V-c as a clear mobile oil (1.83 g, 80%). 1H NMR (300 MHz, CDC13) delta 7.94 (d, J = 5.0 Hz, 1H), 6.77 (d, J= 5.1 Hz, 1H), 4.00 (s, 3H), 2.39 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18368-59-7, its application will become more common.

Reference:
Patent; AB SCIENCE; BENJAHAD, Abdellah; MOUSSY, Alain; CHEVENIER, Emmanuel; PICOUL, Willy; LERMET, Anne; PEZ, Didier; MARTIN, Jason; SANDRINELLI, Franck; WO2013/14170; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 51173-05-8, 5-Fluoro-2-hydroxypyridine, 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, 51173-05-8, blongs to pyridine-derivatives compound. Safety of 5-Fluoro-2-hydroxypyridine

Intermediate 3 was dissolved in sulfuric acid (the larger amounts indicated above) at rt and then heated to 65 C. A preformed solution of fuming nitric acid and sulfuric acid (the smaller amount indicated above) was added dropwise. The temperature was kept between 65 C. and 80 C. (rxn is exothermic and although the bath is at 65 C., temperature goes higher, usually 75, sometimes 80 C.). After the addition was complete, the reaction mixture was heated at 65 C. for an additional hr. The reaction mixture was then cooled to rt and poured in a flask containing ice) (20 g of ice/gr compound, evolution of gas occurred). A solid precipitated out and it was collected by filtration (1HNM? showed intermediate 4 and something else (discarded)). The aqueous layer was extracted with AcOEt several times (3-5) and concentrated on a rotary evaporator under vacuum to afford a solid that was triturated with ether to afford intermediate 4 as a bright yellow solid. A total of 117 g of desired product was collected in the first crop (27% yield from diazonium salt). A portion did not crystallize: this oil was triturated with MeOH and Et2O to afford 3.6 g of intermediate 4; another precipitation from the mother liquid afforded an additional 6.23 g of the desired product intermediate 4. Total: 117.0+3.6+6.23=126.83. 30.4%). Yield for 3 steps (decomposition of diazonium salt; deprotection and nitration). Analytical data from Notebook: 53877-115: 1HNMR(delta, MeOD): 8.56-8.27 (dd, J=7.5, 3.3 Hz, 1H), 8.01 (d, J=3.3 Hz, 1H); LC/MS(M+1)+=158.9; rt=0.15 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,51173-05-8, its application will become more common.

Reference:
Patent; Kadow, John F.; Regueiro-Ren, Alicia; US2006/142298; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 175204-80-5, 3-Amino-4-(trifluoromethyl)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, Safety of 3-Amino-4-(trifluoromethyl)pyridine, blongs to pyridine-derivatives compound. Safety of 3-Amino-4-(trifluoromethyl)pyridine

Example 22. Synthesis of Compound 131 Tert-butyl 4-[[4-(trifluoromethyl)pyridin-3-yl]amino]-5H,6H,7H,8H-pyrido[3,4-d]pyrimidine-7-carboxylate To a stirred mixture of tert-butyl 4-chloro-5H,6H,7H,8H-pyrido[3,4-d]pyrimidine-7-carboxylate (500 mg, 1.854 mmol, 1 equiv.) and 4-(trifluoromethyl)pyridin-3-amine (601.03 mg, 3.707 mmol, 2.0 equiv.) in 1,4-dioxane (5 mL) were added Pd(AcO)2 (83.24 mg, 0.371 mmol, 0.2 equiv.) and Cs2CO3 (1207.95 mg, 3.707 mmol, 2.0 equiv.) and XantPhos (429.04 mg, 0.741 mmol, 0.4 equiv.) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 2 h at 110 degrees C. under nitrogen atmosphere. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The resulting mixture was filtered, the filter cake was washed with DCM (3*2 mL). The filtrate was concentrated under reduced pressure. The resulting mixture was concentrated under reduced pressure. The crude product was purified by reverse phase flash with the following conditions (Column:C18,120 g; Mobile Phase A:Water/0.05% NH4HCO3, Mobile Phase B:ACN; Flow rate:45 mL/min; Gradient: 45% B to 65% B in 15 min; Detector, 254 nm and 220 nm, the desired product were collected at 64% B) to afford tert-butyl 4-[[4-(trifluoromethyl)pyridin-3-yl]amino]-5H,6H,7H,8H-pyrido[3,4-d]pyrimidine-7-carboxylate (600 mg, 81.86%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175204-80-5, 3-Amino-4-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Goldfinch Bio, Inc.; Ledeboer, Mark W.; Daniels, Matthew H.; Yu, Maolin; Harmange, Jean-Christophe P.; US2020/102301; (2020); 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. 131747-53-0, name is (6-(Trifluoromethyl)pyridin-2-yl)methanol, the common compound, a new synthetic route is introduced below. Computed Properties of C7H6F3NO

Examples 29-32A 0.125 M stock solution of tert-butyl (3RS)-3-(4-hydroxyphenyl)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate in dichloromethane (1.0 mL, 0.125 mmol) was added to each vial containing the appropriate alcohol (0.150 mmol). A 0.1 M PS-PPh3 suspension in dichloromethane (2 mL) and a 0.2 M DBAD solution in dichloromethane (1 mL) were added to each vial. The vials were capped and shaken at RT for 24 hours. The reaction mixtures were filtered and concentrated. The resultant residues were treated with 25% trifluoroacetic acid/dichloromethane (1.5 ml_) and shaken for 2 hours at RT. The reactions were concentrated and the resultant residues were treated with a 0.0625 M solution of phenyl (3,4-dimethylisoxazol-5-yl)carbamate in acetonitrile (2 ml_) followed by triethylamine (0.250 ml_). After shaking overnight at room temperature, the vials were concentrated. The residues were dissolved in DMSO (1.5 ml_) and purified by reverse phase HPLC (acetonitrile/water/0.01 % trifluoroacetic acid/0.04% formic acid) to give racemic Examples 29-32. The purified compounds were analyzed by LCMS (Phenomenex Gemini C18 4.6 X 50 mm 5mum; 0.04% Formic Acid, 0.01 % TFA / MeCN).

The synthetic route of 131747-53-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; LONG, Scott Allen; MEYERS, Marvin Jay; PELC, Matthew James; SCHWEITZER, Barbara Ann; THORARENSEN, Atli; WANG, Lijuan Jane; WO2010/58318; (2010); 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. 94170-15-7, name is 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde. A new synthetic method of this compound is introduced below., Recommanded Product: 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde

(i) Ethyl beta-(N-methyl-2-oxo-4-pyridyl)acrylate N-Methyl-4-formyl-2-pyridone* (30.17 g), monoethyl malonate (38.15 g), pyridine (150 ml) and piperidine (3 ml) were stirred under reflux for 61/2 hours. The reaction mixture was evaporated under reduced pressure to afford a residue which was crystallized from aqueous isopropanol to give ethyl beta-(N-methyl-2-oxo-4-pyridyl)acrylate as a pale yellow solid (18.44 g), m.p. 126-7 C.

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, 94170-15-7, 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4540699; (1985); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 18699-87-1, 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. 18699-87-1, name is 2-Methyl-3-nitropyridine. A new synthetic method of this compound is introduced below.

5a N-(2-methylpyridin-3-yl)hydroxylamine STR68 A mixture of 19.6 g (14.2 mmol) of 2-methyl-3-nitropyridine (Synth. Commun. 1990, 20, 2965) in 200 ml of N-methylmorpholine is hydrogenated in the presence of 1 g of 5% platinum/charcoal. During this process, the temperature of the reaction mixture rises to approximately 35 C. After approximately 4.5 hours, the uptake of hydrogen has ceased, and the reaction mixture is filtered with suction through kieselguhr. The filter residue is washed with N-methylmorpholine, and the combined organic phases are concentrated in vacuo (T<45 C.). The residue is taken up in 100 ml of Solvesso 150 (b.p.=185-205 C.) and the resulting mixture is concentrated under a high vacuum (T<80 C.). The residue crystallizes and is digested in hexane. This gives 17.2 g (98%) of the title compound as a pale beige solid. 1 H NMR (CDCl3; delta in ppm): 8.35 (d,1H,NH); 8.15 (s,broad,1H,OH); 7.85 (dd,1H, pyridyl); 7.25 (d,broad,1H, pyridyl); 7.05 (dd,1H, pyridyl); 2.2 (s,3H, CH3). At the same time, in my other blogs, there are other synthetic methods of this type of compound,18699-87-1, 2-Methyl-3-nitropyridine, and friends who are interested can also refer to it. Reference:
Patent; BASF Aktiengesellschaft; US5977146; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 131747-53-0, 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 131747-53-0, name is (6-(Trifluoromethyl)pyridin-2-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Step 3 (6-Trifluoromethylpyridin-2-yl) methanol (760 mg, 4.3 mmol) was dissolved in CH2C12 and THIONYL chloride was added slowly at room temperature. The reaction mixture was stirred at room temperature for 4 h. Solvent was removed under the reduced pressure, the pH was adjusted to 5, and the product was extracted with EtOAc. Purification by flash column (5% EtOAc-Hexane) gave 2-chloromethyl-6-trifluoromethylpyridine (200 mg) as a white solid.

According to the analysis of related databases, 131747-53-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AXYS PHARMACEUTICALS, INC.; WO2005/28429; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 97944-43-9, 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. 97944-43-9, name is 3-Bromo-5-methylpyridin-4-amine, molecular formula is C6H7BrN2, 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: A mixture of 1-38 (350 mg, 1.471 mmol), isoprenylboronic acid pinacol ester [126726- 62-3] (414.632 pL, 2.21 mmol) and Pd(PPh3)4 (169.937 mg, 0.15 mmol) in NaEC03 sat. solution (2 mL) and l,4-dioxane (3.76 mL, 44.1 mmol) was stirred and heated under nitrogen atmosphere for 15 min at 130 C in a MW. The mixture was treated with sat. NaHC03 and extracted with EtOAc. The organic layer was separated, dried (MgS04), filtered and the solvents were evaporated in vacuo. The product was purified flash column chromatography (silica, heptane/EtOAc, gradient from 100/0 to 50/50) to obtain 1-39 (205 mg, 92%) as a colourless oil.

According to the analysis of related databases, 97944-43-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; TRESADERN, Gary John; MARTINEZ LAMENCA, Carolina; LEENAERTS, Joseph Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (171 pag.)WO2019/243535; (2019); 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. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Example 92 Synthesis of 2-amino-5-cyclopropylnicotinonitrile. To a mixture of 2-amino-5-bromonicotinonitrile (1 g, 5.1 mmol), cyclopropylboronic acid (647 mg, 7.6 mmol) and K3PO4 (3.78 g, 17.85 mmol) in toluene/H2O (20 mL/2 mL) was added Pd(OAc)2 (114 mg, 0.51 mmol) and SPhos (209 mg, 0.51 mmol). The mixture was stirred at 95 C. for 16 h. The reaction was cooled to RT and the reaction residue was filtered. The filtrate was concentrated to give the crude product which was purified by silica gel chromatography (EA/PE=4/1) to give 2-amino-5-cyclopropylnicotinonitrile (570 mg, yield: 71%) as a yellow solid. ESI-MS [M+H]+: 160.1.

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, 709652-82-4, 2-Amino-5-bromonicotinonitrile.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem