Tag: M.W:100-200

Reference of 18699-87-1, 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 18699-87-1 as follows.

3-Nitro-2-pyridinecarbaldehyde; 2-Methyl-3-nitropyridine (24 g, 173.91 mmol) was dissolved in 1,4-dioxane (500 mL) and to the mixture was added selenium dioxide (23 g, 208.7 mmol) and the mixture was heated under reflux for 16 h. After completion of reaction, the mixture was cooled to rt and filtered through Celite and the filtrate was concentrated under reduced pressure to give thick oily mass. The oily mass was purified by silical gel column chromatography using 20% of ethyl acetate and hexane as eluent to give 3-nitro-2-pyridinecarbaldehyde as an off white solid: 1H-NMR (CDCl3) delta: 7.7 (m, 1H), 8.3 (d, 1H), 9.0 (d, 1H), 10.3 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18699-87-1, its application will become more common.

Reference:
Patent; AMGEN INC.; US2011/152296; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 52378-63-9, 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.52378-63-9, name is (3-Aminopyridin-2-yl)methanol, molecular formula is C6H8N2O, molecular weight is 124.14, as common compound, the synthetic route is as follows.

Neat (3-aminopyridin-2-yl)methanol (may be prepared as described in Description 80; 68 mg, 0.55 mmol) was added in one charge to a stirred suspension of 2- [(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79;120 mg, 0.393 mmol), EDC (151 mg, 0.786 mmoi), HOBT (120 mg, 0.79 mmol) and triethylamine (0.11 ml, 0.79 mmol) in N,N-dimethylformamide (1.5 ml) in air at 15 C. The reaction mixture was stirred at 15 C overnight. Water (30 ml) was added and the reaction mixture extracted with ethyl acetate (30 ml x 3). The organic phases were dried with Na2S04 and concentrated. The residue was purified by pre-HPLC(instrument: Gilson-281 , Column: WATERS XBRIDGE 30-100MM SUM, Mobile Phase : A: 0.04%NH3H2O B:CH3CN, Flow rate: 30.0ml/L, Gradient: 0-10min, B = 30-38% RT= P1 : 7.0min; P2: 9.5min) to yield the title compound as a white solid. 20 mg,HNMR (400MHz, D SO-d6); 10.82 (s, 1 H), 8.57-8.63 (m, 3H), 8.35-8.36 (m, H), 8.27- 8.29 (m, 1 H), 7.95-7.97 (m, 1 H), 7.70-7.71 (m, 2H), 7.53-7.55 (m, 2H), 7.32-7.41 (m, 5H), 5,54 (s, 2H), 4.65 (s, 2H).MS (electrospray): m/z [M+H]+ = 412

Statistics shows that 52378-63-9 is playing an increasingly important role. we look forward to future research findings about (3-Aminopyridin-2-yl)methanol.

Reference:
Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 100202-78-6 ,Some common heterocyclic compound, 100202-78-6, molecular formula is C6H5BrFN, 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 solution of 3-methylpyrazole-4-boronic acid pinacol ester (1.51 g, 7.26 mmol) in DMF (40 mL) was added 2-Methyl) -6-fluoropyridine (2.1 g, 11 mmol), Cs2CO3 (8.3 g, 25 mmol) and KI (0.6 g, 4 mmol) were added and then reacted at 70 C overnight. The reaction solution was concentrated under reduced pressure to remove DMF, water (40 mL) was added thereto and extracted with methylene chloride (50 mL × 3). The organic phase was washed with anhydrousNa2SO4 and the concentrated crude product was purified by silica gel column chromatography (eluent: PE / EtOAc (v / v) = 4/1) to give1.5 g of a yellow oil, yield: 65%.

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. 100202-78-6, 2-(Bromomethyl)-6-fluoropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Bing; Bai Shun; Zhou Youbo; Yang Tiping; He Wei; Zhang Yingjun; Zheng Changchun; (103 pag.)CN106749268; (2017); A;,
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.70593-61-2, name is 6-Chloropicolinamide, molecular formula is C6H5ClN2O, molecular weight is 156.5697, as common compound, the synthetic route is as follows.Recommanded Product: 70593-61-2

a 6-(3,4-Dihydro-1H-isoquinolin-2-yl)-pyridine-2-carboxylic acid amide Following the general method described in example 1, the title compound was obtained as a light yellow crystalline material by reaction of 6-chloro-pyridine-2-carboxylic acid amide with 1,2,3,4-tetrahydro-isoquinoline and crystallization of the free base. Mp. 145-150 C. (AcOEt/hexane), MS: m/e=253 (M+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,70593-61-2, 6-Chloropicolinamide, and friends who are interested can also refer to it.

Reference:
Patent; Alanine, Alexander; Buettelmann, Bernd; Heitz Neidhart, Marie-Paule; Pinard, Emmanuel; Wyler, Rene; US2003/119870; (2003); 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.52311-50-9, name is 2-Chloro-4-ethoxypyridine, molecular formula is C7H8ClNO, molecular weight is 157.6, as common compound, the synthetic route is as follows.Safety of 2-Chloro-4-ethoxypyridine

A mixture of 2-chloro-4-ethoxypyridine (200 mg, 1.3 mmol), cyclohexanamine (152 mg, 1.47 mmol), Pd2(dba)3 (12 mg, 0.013 mmol), BINAP (40 mg, 0.064 mmol), NaOt-Bu (244 mg, 2.53 mmol) and toluene (5 mL) in a 50 mL round bottom flask fitted with a reflux condenser was heated at 100 C. for 4 h under a N2 atmosphere. The crude reaction mixture was concentrated to dryness to give the title compound as a red oil that was used in subsequent reactions without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52311-50-9, 2-Chloro-4-ethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; McClure, Kelly; Tanis, Virginia M.; Fennema, Elizabeth G.; Lebsack, Alec D.; Martin, Connor L.; Venkatesan, Hariharan; Xue, Xiaohua; Woods, Craig R.; (531 pag.)US2017/313691; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 20970-75-6, 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. 20970-75-6, name is 2-Cyano-3-methylpyridine. A new synthetic method of this compound is introduced below.

A mixture of 3-methylpicolinonitrile (2 g, 16.9 mmol, 1.0 eq), NBS (3 g, 16.9 mmol, 1.0 eq) and BPO (41 1 mg, 1.7 mmol, 0.1 eq) in CCU (30 mL) was refluxed and stirred overnight. Then the mixture was cooled to rt and concentrated. The residue was diluted with water (50 mL), extracted with DCM (50 mLx3). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2S04 and concentrated. The residue was purified on silica gel column (PE/EtOAc = 5/1) to afford 3-(bromomethyl)picolinonitrile as a brown solid (2.1 g, 63%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,20970-75-6, its application will become more common.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; WO2015/103317; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 52334-51-7, 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. 52334-51-7, name is 3-Amino-5-methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

Step 1. 6-methyl[1,3]oxazolo[5,4-b]pyridine-2(1H)-thione3-Amino-5-methylpyridin-2-ol (0.21 g, 1.7 mmol) was dissolved in THF (5 mL), and 1,1′-thiocarbonyldiimidazole (0.48 g, 2.7 mmol) was added. The mixture was stirred at RT for 20 min. The reaction was diluted with water, treated with 1N HCl to adjust the pH to the range of 4-5. The product was then extracted with ethyl acetate, the extracts were washed with brine, and dried over sodium sulfate, filtered and concentrated to afford the product, used without further purification in the following step. LCMS (M+H)+: m/z=167.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52334-51-7, 3-Amino-5-methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Rodgers, James D.; Shepard, Stacey; Arvanitis, Argyrios G.; Wang, Haisheng; Storace, Louis; Folmer, Beverly; Shao, Lixin; Zhu, Wenyu; Glenn, Joseph; US2010/298334; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1083197-78-7, 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. 1083197-78-7, name is 4-(Trifluoromethyl)nicotinaldehyde, molecular formula is C7H4F3NO, 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.

A 50-mL round-bottom flask was charged with 5-cyanopyridin-3-yl (R)-2-methylpiperazine-1-carboxylate (179 mg, 0.727 mmol, 1.20 equiv), 4-(trifluoromethyl)pyridine-3-carbaldehyde (106 mg, 0.606 mmol, 1.00 equiv), triethylamine (184 mg, 1.82 mmol, 3.00 equiv), and 1,2-dichloroethane (10 mL). The mixture was stirred for 1 hour at room temperature prior to addition of sodium triacetoxyborohydride (386 mg, 1.82 mmol, 3.00 equiv). The reaction was stirred overnight at room temperature and quenched with water (30 mL). The resulting solution was extracted with dichloromethane (2*50 mL) and the organic layers were combined, washed with brine (2*30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product (300 mg) was purified by preparative HPLC to afford 94.9 mg (39% yield) of 5-cyanopyridin-3-yl (R)-2-methyl-4-((4-(trifluoromethyl)pyridin-3-yl)methyl)piperazine-1-carboxylate as a yellow oil. 1H NMR (300 MHz, Chloroform-d) delta 9.02 (s, 1H), 8.71-8.73 (m, 2H), 8.64 (s, 1H), 7.84 (s, 1H), 7.54 (d, J=5.1 Hz, 1H), 4.41 (br, 1H), 3.99-4.03 (m, 1H), 3.73 (s, 2H), 3.48 (br, 1H), 2.84-2.87 (m, 1H), 2.69-2.73 (m, 1H), 2.42-2.47 (m, 1H), 2.01-2.31 (m, 1H), 1.41-1.42 (m, 3H). LCMS (ESI, m/z): 406 [M+H]+.

According to the analysis of related databases, 1083197-78-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; CISAR, Justin S.; DUNCAN, Katharine K.; FENG, Yu; WIENER, John J.M.; WEBER, Olivia D.; (79 pag.)US2018/256566; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63237-88-7, 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 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Example 97N-((ls,4s)-4-(2-(4′-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)-3′-hydroxybiphenyl-3- yloxyJ-S-fluoronicotinamidoJcyclohexylJpyrazolo [ 1 ,5-a] pyridine-2-carboxamide To a solution of pyrazolo[l,5-a]pyridine-2-carboxylic acid (30.8 mg, 0.19 mmol) in acetonitrile (3 mL) was added DIPEA (0.066 mL, 0.38 mmol). To this mixture was then added HATU (72.3 mg, 0.19 mmol). The mixture was stirred at RT for 10 min before it was added to a solution of N-((ls,4s)-4-aminocyclohexyl)-2-(4′-(((3S,5R)-3,5-dimethylpiperazin- l-yl)methyl)-3′-hydroxybiphenyl-3-yloxy)-5-fluoronicotinamide, hydrochloride (125 mg, 0.19 mmol) and DIPEA (0.066 mL, 0.38 mmol) in acetonitrile (3 mL). The mixture was stirred at RT overnight. 1 mL water and 1 mL acetic acid was then added to the mixture before being purified using reverse phase preparative HPLC (eluent = TFA(aq)/MeCN). The appropriate fractions were combined and evaporated to give a residue. This was triturated with ether to give the title compound as a solid which was isolated by filtration and dried overnight under vacuum at 400C. Yield: 96 mg 1H NMR (400 MHz, CD3OD) delta 8.48 (d, J = 7.4 Hz, IH), 8.43 (d, J = 7.2 Hz, IH), 8.12 (d, J = 3.1 Hz, IH), 8.06 (dd, J = 7.9, 3.1 Hz, IH), 7.66 (d, J = 9.0 Hz, IH), 7.51 – 7.43 (m, 2H), 7.40 – 7.37 (m, IH), 7.25 – 7.17 (m, 3H), 7.10 – 7.07 (m, 2H), 6.97 – 6.93 (m, 2H), 4.17 – 4.11 (m, IH), 4.07 (s, IH), 4.04 – 3.99 (m, IH), 3.58 – 3.51 (m, 2H), 3.45 – 3.40 (m, 2H), 2.64 (t, J = 12.6 Hz, 2H), 1.92 – 1.70 (m, 8H), 1.31 (d, J = 6.4 Hz, 6H). MS: [M+H]+=692.2 (calc=692.336) (MultiMode+)

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, 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.

N-[4-(5-Cyano-2-methoxy-pyridin-3-yl)-benzyl]-2-trifluoromethoxy-benzenesulfonamide To a solution of 4-aminomethylphenylboronic acid hydrochloride (2.0 g, 13.2 mmol) in methanol (20 ml) was added di-tert-butyl dicarbonate (3.16 g, 15.5 mmol) and sodium bicarbonate (3.32 g, 19.8 mmol). The mixture was sonicated for 4 h then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and the solvent evaporated to give (4-bromo-benzyl)-carbamic acid tert-butyl ester (1.8 g, 13.2 mmol, 100%) as a white solid. To 6-chloro-nicotinonitrile (15 g, 0.11 mol) under argon atmosphere was added 25% sodium methoxide in methanol (11.7 g, 0.22 mol) and the mixture heated under reflux for 20 h. The methanol was evaporated and the residue partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with water, brine, dried over anhydrous magnesium sulfate and the solvent evaporated to give 6-methoxy-nicotinonitrile (17.0 g, 0.13 mol, 117%) as a white solid. To 6-methoxy-nicotinonitrile (13.2 g, 99 mmol) in acetic acid (32 ml) was added sodium acetate (8.1 g, 99 mmol). The mixture was stirred and a solution of bromine (31.5 g, 197 mmol) in acetic acid (32 ml) added. The mixture was heated to 80 C. for 48 h. The reaction mixture was poured into water and extracted with diethyl ether. The organic phase was washed with 4M aqueous sodium hydroxide solution, 5% sodium thiosulfate solution, dried over anhydrous potassium carbonate and the solvent was evaporated to give 5-bromo-6-methoxy-nicotinonitrile (11.9 g, 56 mmol, 57%). To a solution of 2-methoxy-5-cyanopyridine-3-boronic acid (1.0 g, 4.0 mmol) in 1,2-dimethoxyethane (10 ml) was added (4-bromo-benzyl)-carbamic acid tert-butyl ester (0.42 g, 2.0 mmol), tetrakis(triphenylphosphine)palladium (0) (114 mg, 0.1 mmol) and 2M aqueous sodium carbonate (1 ml, 2.0 mmol). The reaction was heated to 150 C. for 10 min in a microwave over. The mixture was concentrated under reduced pressure and partitioned between ethyl acetate and water. The organic phase was washed with water, then brine, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was purified on silica gel eluting with 5:1 heptane/ethyl acetate to give [4-(5-cyano-2-methoxy-pyridin-3-yl)-benzyl]-carbamic acid tert-butyl ester as a white solid (0.5 g, 1.47 mmol, 37%). To a solution of [4-(5-cyano-2-methoxy-pyridin-3-yl)-benzyl]-carbamic acid tert-butyl ester (0.5 g, 1.5 mmol) in dichloromethane (5 ml) at 0 C. was added trifluoroacetic acid (5 ml, 28 mmol). The reaction mixture was stirred for 30 min at 0 C. before the solvent was evaporated and the residue purified on a SCX column (eluted with 2M ammonia in methanol) to give 5-(4-aminomethyl-phenyl)-6-methoxy-nicotinonitrile as a clear glass (0.39 g, 1.6 mmol, 107%). To a solution of 5-(4-aminomethyl-phenyl)-6-methoxy-nicotinonitrile (57.3 mg, 0.24 mmol) in dichloromethane (2 ml) was added triethylamine (73.0 mg, 0.72 mmol) and 2-(trifluoromethoxy)benzenesulfonyl chloride. The reaction mixture was agitated for 20 hours and the solvent evaporated under reduced pressure. The crude product was taken up in dimethyl sulfoxide (1 ml) and purified by preparatory LCMS. The solvent was evaporated under reduced pressure to give the title compound (19.1 mg, 0.04 mmol, 17%). 1H NMR (400 MHz, DMSO-d6): delta 8.68 (d, 1H), 8.47 (t, 1H), 8.15 (d, 1H), 7.90 (m, 1H), 7.73 (m, 1H), 7.45-7.55 (m, 4H), 7.31 (d, 2H), 4.19 (d, 2H), 3.96 (s, 3H) ppm; MS (ESI) m/z: 464.3 [M+H]+.

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 33252-28-7, 6-Chloronicotinonitrile.

Reference:
Patent; N.V. Organon; Pharmacopeia Drug Discovery Inc.; US2007/149577; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem