Day: April 19, 2022

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

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: 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

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

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. 885277-48-5, name is Methyl 2-bromo-6-methylnicotinate. A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-bromo-6-methylnicotinate

To a stirred solution of methyl 2-bromo-6-methylnicotinate (US2010144760, 2.79 g, 12.1 1 mmol) in acetonitrile (50 ml) (degassed by N2 purge separately) was added bis(triphenylphosphine)palladium(II) chloride (1.063 g, 1.514 mmol). The reaction mixture was heated up to 70 C and diisopropyl ethyl amine (7.83 g, 60.6 mmol) was added slowly, followed by a solution of (R)-4-(4-(3-ethynylcyclopent-2- en- l-yl)piperazin- l-yl)benzonitrile (Compound lj, 2.8 g, 10.10 mmol) in acetonitrile (20 ml) was added slowly at the same temperature. The reaction mixture was heated and stirred at 80-85 C for 14 hrs. The progress of the reaction was monitored by TLC. The reaction mixture was distilled under vaccum to dryness to obtain a crude product which was purified by column chromatography over silica gel (100-200 mesh) using 60-80% ethyl acetate in hexane as an eluent to obtain the title product (0.9 gm, 20.90 % yield). iH NMR (400 MHz, CDC13) delta 8.17 (d, J = 8.1 Hz, 1H), 7.52 (d, J = 8.5 Hz, 2H), 7.20 (d, J = 8.2 Hz, 1H), 6.90 – 6.87 (m, 2H), 6.36 (d, J = 2.3 Hz, 1H), 4.08 – 4.03 (m, 1H), 3.96 (s, 3H), 3.40 – 3.35 (m, 4H), 2.75 – 2.67 (m, 6H), 2.64 (s, 3H), 2.13 – 2.09 (m, 1H), 2.03 – 1.95 (m, 1H). MS: m/z 427.24 (M+l).

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, 885277-48-5, Methyl 2-bromo-6-methylnicotinate.

Reference:
Patent; LUPIN LIMITED; KARCHE, Navnath, Popat; TILEKAR, Ajay, Ramchandra; KURHADE, Sanjay, Pralhad; JADHAV, Ganesh, Rajaram; GUPTA, Nishant, Ramniwasji; SINHA, Neelima; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; (191 pag.)WO2017/29601; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 179687-79-7, 2-((2-Chloro-4-nitrophenoxy)methyl)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, Formula: C12H9ClN2O3, blongs to pyridine-derivatives compound. Formula: C12H9ClN2O3

Step 2: 3-chloro-4-(pyridin-2-ylmethoxy)aniline The 2-((2-chloro-4-nitrophenoxy)methyl)pyridine (3.9 g, 15 mmol), zinc powder (5.8 g, 88 mmol) and ammonium chloride (2.4 g, 44 mmol) were added into a mixed solution of ethanol (60 mL) and H2O (10 mL). The mixture was stirred at 60 C. overnight. Then the reaction mixture was poured into 200 mL of H2O, extracted with ethyl acetate. The organic phase was separated, washed with saturated brine and dried. The solvent was removed in vacuo, and the compound shown in the title (3.4 g, 98%) was obtained. 1H NMR (CDCl3): delta 8.57 (1H, d, J=4.8 Hz), 7.75-7.70 (1H, m), 7.65-7.63 (1H, m), 7.23-7.20 (1H, m), 6.81 (1H, d, J=9.2 Hz), 6.77 (1H, d, J=2.8 Hz), 5.18 (2H, s), 3.48 (2H, br).

The synthetic route of 179687-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; CENTAURUS BIOPHARMA CO., LTD.; LIANYUNGANG RUNZHONG PHARMACEUTICAL CO., LTD.; XIAO, Dengming; ZHU, Yan; HU, Yuandong; WANG, Huting; LI, Jijun; PENG, Yong; ZHANG, Hui; LUO, Hong; KONG, Fansheng; HAN, Yongxin; (25 pag.)US2016/214964; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 821791-58-6, Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate, 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, 821791-58-6, blongs to pyridine-derivatives compound. HPLC of Formula: C9H10ClNO3

4-CHLORO-1-METHYL-6-OXO-1, 6-DIHYDRO-PYRIDINE-3-CARBOXYLIC acid ethyl ester (2.65 g, 12.3 MMOL) was dissolved in a mixture of tetrahydrofuran (16 mL), acetonitrile (16 mL) and water (8 mL). Sodium hydroxide (1.23 g, 30.8 MMOL) was added and the reaction mixture was allowed to stir at ambient temperature for 24 h. The reaction mixture was diluted with water (50 mL) and was acidified to pH 2 with 1 M hydrochloric acid and was extracted many times with ethyl acetate (about 1 L). The extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to afford an orange-tinged solid. Crystallization from methanol-ethyl acetate afforded 4-CHLORO-1-METHYL-6-OXO-1, 6-DIHYDRO-PYRIDINE-3-CARBOXYLIC acid (0.859 g, 37 % yield) as an off-white solid :’H NMR (DMSO-D6, 400 MHz) 8 13.02 (br s, 1 H), 8.58 (s, 1 H), 6.58 (s, 1 H), 3.48 (s, 3 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,821791-58-6, its application will become more common.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/818; (2005); 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. 64264-15-9, name is 2-(Pyridin-2-yl)pyrimidin-4-ol. This compound has unique chemical properties. The synthetic route is as follows. Formula: C9H7N3O

4-Chloro-2-pvridin-2-vl-pyrimidine; 2-Pyridin-2-yl-3H-pyrimidin-4-one, (0.945g, 5.45 mmol) was stirred in dichloromethane (25 mL) and phosphorous oxychloride (10 mL, 107 mmol) at 80C for 1 h. The phosphorous oxychloride and dichloromethane was removed by vacuo. Crushed ice (50 mL) was added to the reaction mixture followed by K2CO3 (1 M, aq. ) until pH reached 7. The resulting mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were extracted with brine (1×30 mL) and dried (MgS04). The solvent was evaporated to give the title compound (0.975 g, 93%). ‘H NMR (400 MHz, dmso-d6) 8 7.6 (t, J=5. 5 Hz, 1 H) 7.8 (d, J=5. 1 Hz, 1 H) 8.0 (td, J=7. 8,1. 2 Hz, 1 H) 8.4 (d,. J=7. 7 Hz, 1 H) 8.8 (m, 1 H) 8.9 (d, J=5. 0 Hz, 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, 64264-15-9, 2-(Pyridin-2-yl)pyrimidin-4-ol.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2005/82884; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1044872-40-3, 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 1044872-40-3 as follows.

To a solution of methyl 2-amino-4,6-dichloro-pyridine-3-carboxylate (300 mg, 1.357 mmol) in dry THF (7 mL) was added a 3M solution of methylmagnesium bromide in diethyl ether (1.58 mL, 4.75 mmol) dropwise under nitrogen at -60 C. The reaction mixture was stirred at -60 C to 0 C for 1 h. The progress of reaction was monitored by TLC & 1H NMR. After completion of reaction, the mixture was quenched using aqueous saturated solution of ammonium chloride and extracted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography on silica (100:200 mesh) using 10% EtOAc-hexane system as eluent to afford 2-(2-amino-4,6-dichloro-3-pyridyl)propan- 2-ol (263 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1044872-40-3, its application will become more common.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; PUJALA, Brahmam; SHINDE, Bharat Uttam; NAYAK, Anjan Kumar; CHAKLAN, Naveen; AGARWAL, Anil Kumar; RAMACHANDRAN, Sreekanth A.; PHAM, Son; WO2015/103355; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 142896-15-9, 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 142896-15-9, name is Methyl 2,6-dimethylisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

120ml?CCl4?1.372g(8.3mmol)?(3)?60mg?AIBN???2.866g(16.1mmol)?NBS??????????????100W??????????8???????????????????????????200ml??NaHCO3??????????(CCl4)???????????50ml?H2O?4?????????????????100ml?H2O???????(Na2SO4)???????????????????????????????????????[?:???????-CH2Cl2(80/20)?CH2Cl2]?????????????????????????????????????????????????????????????(4)??1???????????????

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 142896-15-9, Methyl 2,6-dimethylisonicotinate.

Reference:
Patent; CIS BIO INTERNATIONAL, CIS; JP2004/509075; (2004); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem