Tag: M.W:100-200

Application of 16744-81-3, 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.16744-81-3, name is 4-Methoxypicolinaldehyde, molecular formula is C7H7NO2, molecular weight is 137.14, as common compound, the synthetic route is as follows.

A mixture of 45 G of 4-METHOXYPYRIDINE-2-CARBALDEHYDE (Ashimori et AL., Chem. Pharm. Bull. 38, 2446- 2458 (1990) ), 75.80 G of pyridine hydrochloride, 102.45 G of monomethyl malonate potassium salt and 4.1 mi of piperidin in 700 ML of pyridine are slowly heated, with stirring, to 120 C. When the evolution of gas starts, the heating source is temporarily removed to stop the reaction from becoming too violent. Once the reaction has subsided, the mixture is stirred at 120 C for a further 2.5 h, and the pyridine is then distilled off under reduced pressure. The residue is partitioned between ethyl acetate/water and the organic phase is washed with water and dried. The residue obtained after concentration is chroma- tographed on a silica gel column using ethyl ACETATE/PETROLEUM ether 2: 1. This initially gives 43.2 G of the title compound as a yellow oil which crystallizes on standing and then shows a m. p. of 80-82 C. The mass spectrum shows the molecular peak MHD AT 194 DA.

Statistics shows that 16744-81-3 is playing an increasingly important role. we look forward to future research findings about 4-Methoxypicolinaldehyde.

Reference:
Patent; ALTANA PHARMA AG; WO2004/76451; (2004); 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.846036-96-2, name is (4-Amino-6-chloropyridin-3-yl)methanol, molecular formula is C6H7ClN2O, molecular weight is 158.59, as common compound, the synthetic route is as follows.HPLC of Formula: C6H7ClN2O

(4-Amino-6-chloropyridin-3-yl)methanol (2.6 g, 16.4 mmol) was dissolved in DCM (80 mL) along with Mn02 (14.3 g). The mixture was stirred at rt for 24 h. Mn02 was filtered off andthe filtrate was concentrated to afford 4-amino-6-chloronicotinaldehyde (1.67 g, 65%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,846036-96-2, (4-Amino-6-chloropyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; PRINCIPIA BIOPHARMA, INC.; VERNER, Erik; BRAMELD, Kenneth Albert; WO2015/120049; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72587-18-9 ,Some common heterocyclic compound, 72587-18-9, molecular formula is C6H4ClF3N2, 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.

(4) 2.50 g of 6-chloro-3- (ethanesulfonyl) pyridine-2-carboxylic acid,And 30 mL of toluene were added 1.31 g of thionyl chloride,And one drop of DMF were heated under reflux for 3 hours.The reaction mixture was concentrated and dissolved in 30 mL of tetrahydrofuran, and under ice cooling,1.97 g of 3-amino-2-chloro-5- (trifluoromethyl) pyridine,And triethylamine (1.10 g) were added dropwise thereto.After stirring at room temperature for 3 hours,The reaction mixture was added to ice water and extracted with ethyl acetate.The obtained organic layer was washed with saturated brine,After drying over anhydrous magnesium sulfate, it was concentrated.The residue was subjected to silica gel column chromatography,2.4 g of Intermediate 36 described below was obtained.

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. 72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical; Ikari, Kaori; (123 pag.)JP2019/6686; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 63572-73-6, 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 63572-73-6, name is 5-Nitro-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

10% Palladium on carbon (40 mg) was added to a solution of 5-nitro-1H-pyrazolo[3,4-b]pyridine (A) (308 mg, 1.876 mmol) in ethanol and tetrahydrofuran and the mixture was charged with H2 (gas). After stirring the reaction mixture for 15 h, the mixture was filtered using celite and purified by column chromatography. The desired product 1H-pyrazolo[3,4-b]pyridin-5-amine (B) (73 mg) was obtained as 89% yield.

According to the analysis of related databases, 63572-73-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; US2013/29995; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1192813-41-4, 2-(Difluoromethoxy)-5-nitropyridine, 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: 1192813-41-4, blongs to pyridine-derivatives compound. SDS of cas: 1192813-41-4

Step B: 6-(difluoromethoxy)pyridin-3-amine To 2-(difluoromethoxy)-5-nitropyridine (4.7 g, 24.7 mmol) in degassed methanol (100 mL) was added 10% palladium on carbon (500 mg, 0.47 mmol) and the reaction was hydrogenated at atmospheric pressure for 1 hour. To this was added acetic acid (2.83 mL, 49.4 mmol) and the reaction was filtered through Celite and concentrated in vacuo to afford 6-(difluoromethoxy)pyridin-3-amine (6.33 g, 25.9 mmol, 105 % yield) as an olive green liquid. XH NMR (400 MHz, MeOD-d4) delta ppm 7.60 (d, J=2.76 Hz, 1 H), 7.37 (s, 0.5 H), 7.15 (dd, J=8.66, 2.89 Hz, 1 H), 7.00 (s, 0.5 H), 6.71 (d, J=8.78 Hz, 1 H).

The synthetic route of 1192813-41-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, James H.; MCDONALD, Ivar, M.; KING, Dalton; OLSON, Richard, E.; WANG, Nenghui; IWUAGWU, Christiana, I.; ZUSI, Christopher, F.; MACOR, John, E.; WO2011/53292; (2011); 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. 57963-08-3, name is 5,6-Dimethylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. name: 5,6-Dimethylpyridin-2-amine

(A) 5,6-dimethylimidazo[1,2-a]pyridine (0313) A mixture of 5,6-dimethylpyridin-2-amine (2.0 g, 16 mmol), 40% chloroacetaldehyde aqueous solution (3.2 mL, 20 mmol) and ethanol (40 mL) was heated under reflux overnight. The solvent was evaporated under reduced pressure, and the reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the residue was purified by NH silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.5 g). 1H NMR (300 MHz, CDCl3) delta2.35 (3H, s), 2.53 (3H, s), 7.05 (1H, d, J = 9.4 Hz), 7.46 (2H, t, J = 4.5 Hz), 7.65 (1H, d, J = 1.1 Hz).

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, 57963-08-3, 5,6-Dimethylpyridin-2-amine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52311-50-9 ,Some common heterocyclic compound, 52311-50-9, molecular formula is C7H8ClNO, 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 degassed mixture of 4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2- yl)benzamide ( 9.4g, 38 mmol) and 2-chloro-4-ethoxypyridine ( 5g, 31.7 mmol) in dioxane was added Brettphos-prePd (catalytic amount) and CS2CO3 (12.3 g, 37.8 mmol) under N2atmosphere. The mixture was heated to 100 C and stirred for 3.5 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated, and the residue was purified on silic-gel (PE: EA = 100% ~ 30%) to give N-(4-ethoxypyridin-2-yl)-4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzamide (8.8 g, yield 75%). 1HNMR (400MHz, CDC13): 5=8.74 (s, 1 H), 8.05~8.02(m, 1 H), 8.01 (s, 1 H), 7.94-7.89 (m, 4 H), 6.60-6.59 (m, 1 H), 4.20-4.14 (m, 2 H), 1.47-1.43 (m, 3 H), 1.36 (s,12 H), MS (ESI):M/Z (M+l)=369.19.

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. 52311-50-9, 2-Chloro-4-ethoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile. A new synthetic method of this compound is introduced below.

Triethylamine (5.51 g, 4 mL, 54.6 mmol, 2.7 eq) is added to a solution of 6-chloro- nicotinonitrile (2.76 g, 20 mmol, 1 eq), (i?)-2-methyl- piperazine (2.0Og, 20 mmol, 1 eq) in DMF (15 mL), and the resulting solution is stirred at rt for 36 h. A white precipitate of triethylamine hydrochloride forms in the course of the reaction. Water (15 mL) and EtOAc (100 mL) are added, the organic layer is separated, dried over sodium sulfate and concentrated under reduced pressure to a white residue. The solid is further dried under high vacuum to yield the desired product as a white solid (2.3 g, 59%). IH NMR (400 MHz, CHLOROFORM-*/) delta ppm 8.32 (d, J=2.40 Hz, 1 H), 7.52 (dd, J=9.09, 2.27 Hz, 1 H), 6.52 (d, J=8.97 Hz, 1 H), 4.14 – 4.24 (m, 2 H), 3.01 – 3.07 (m, 1 H), 2.72 – 2.94 (m, 3 H), 2.52 (dd, J=12.76, 10.36 Hz, 1 H), 1.07 (d, J=6.32 Hz, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33252-28-7, 6-Chloronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); 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.72141-44-7, name is 4-Chloro-2-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.5709, as common compound, the synthetic route is as follows.SDS of cas: 72141-44-7

(a); 5.76 g (40.1 mmol) of 4-chloro-2-methoxypyridine was dissolved in 20 ml of dimethylformamide, and a dimethylformamide (20 ml) solution of 8.01 g of N-bromosuccinimide (98%, 44.1 mmol) was dropwise added over a period of 30 minutes. After stirring at room temperature for 2 days, an unreacted material was confirmed, and thus 2.85 g of N-bromosuccinimide (98%, 16 mmol) was further added, followed by stirring at room temperature further for 3 days. The reaction mixture was poured into 250 ml of water, followed by extraction with ethyl ether (100 ml each) three times. The organic layer was washed with water (100 ml), a sodium thiosulfate aqueous solution (100 ml) and then a saturated sodium chloride solution (100 ml), dried over magnesium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel chromatography to obtain 7.10 g (yield: 80%) of 5-bromo-4-chloro-2-methoxypyridine. 1H-NMR(CDCl3, 400MHz): delta (ppm) =3.91 (s, 3H), 6. 89 (s,1H), 8.28(s,1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72141-44-7, 4-Chloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1679003; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 98121-41-6, Adding some certain compound to certain chemical reactions, such as: 98121-41-6, name is 3-Amino-5,6-dichloropyridine,molecular formula is C5H4Cl2N2, 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 98121-41-6.

Precursor alpha: 2,3-Dichloro-5-isopropylthiopyridine 13.1 g (0.08 mol) of 3-amino-5,6-dichloropyridine in 120 ml of methylene chloride were reacted with 25 g (0.16 mol) of diisopropyl disulfide and 12.4 g (0.12 mol) of tert-butyl nitrite in 70 ml of methylene chloride by a method similar to Example 1, Precursor alpha. This gave 30 g of the dark oil (approximately 40% of product of value) which was further reacted without further purification. 1H-NMR (in d6 dimethyl sulfoxide): delta [ppm]=1.25 (d, 2*CH3); 3.7 (m, CH); 8.2 and 8.3 (2*d, pyr H).

According to the analysis of related databases, 98121-41-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF Aktiengesellschaft; US6448205; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem