Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 709652-82-4, 2-Amino-5-bromonicotinonitrile, 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, name: 2-Amino-5-bromonicotinonitrile, blongs to pyridine-derivatives compound. name: 2-Amino-5-bromonicotinonitrile

A suspension of 2-amino-5-bromo-3-pyridinecarbonitrile (0.59 g, 3 mmol), DMF-DMA (1 ml, 7.5 mmol), and MeCN (2 ml) was irradiated at 50 C (input power of: 200 W) for2 min. The resulting mixture was cooled to room temperature and poured onto ice cold water. The precipitate was filtered off, washed with water, and dried to afford (1E)-N?-(3-cyano-2-pyridinyl)-N,N-dimethylmethanimidamide (Lacbay et al. 2014). Light yellow solid; yield 95%; m.p. 116-117 C; 1H NMR (400 MHz, DMSO-d6) delta 8.65-8.60 (m, 1H, H-5), 8.46 (d, J = 2.6 Hz, 1H, H-3), 8.32 (d,J = 2.6 Hz, 1H, N=CH), 3.16 (s, 3H, CH3),3.07 (s, 3H,CH3); 13C NMR (100 MHz, DMSO-d6) delta 162.27 (C-2),157.00 (C=N), 153.23 (C-6), 144.32 (C-4), 116.77 (CN), 110.23 (C-5), 102.68 (C-3), 35.00 (C-N); IR (film): 3457(C-N), 3061, 2916, 2795, 2483, 2306, 2214 (CN), 1960, 1625 (C=N), 1562, 1395 cm-1; HRMS (ESI) m/z: calculatedfor C9H10BrN4+ [M + H]+: 253.0089; found: 253.0084.

The synthetic route of 709652-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Ya-Quan; Zong, Chao-Yang; Ji, Jin-Yu; Han, Qing; Chemical Papers; vol. 72; 12; (2018); p. 2965 – 2972;,
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.39903-01-0, name is 2-Amino-5-bromo-3-pyridinol, molecular formula is C5H5BrN2O, molecular weight is 189.01, as common compound, the synthetic route is as follows.COA of Formula: C5H5BrN2O

Preparation 56-Bromo-oxazolo[4,5-b]pyridine[00122] 2-Amino-5-bromo-3-hydroxypyridine (200 mg, 1.06 mmol) is dissolved in 3 ml of triethylortoformate and a catalytic amount of p-toluenesulfonic acid is added. The mixture is heated to reflux for 5 h, then cooled, diluted with DCM and washed with saturated sodium bicarbonate solution. The organic phase is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by flash column chromatography to afford 212 mg (60%) of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39903-01-0, 2-Amino-5-bromo-3-pyridinol, and friends who are interested can also refer to it.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; WEIL, Tanja; HECHENBERGER, Mirko; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; ERDMANE, Elina; SMITS, Gints; WO2011/15343; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 130473-27-7, 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. 130473-27-7, name is 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

Coupling: Example 24 is obtained as a white solid (40% yield) using acid C176 using Method C with non-critical changes. HRMS (FAB) calculated for C15H18N4O+H: 271.1559, found 271.1562 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,130473-27-7, 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (2003); 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. 66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine. A new synthetic method of this compound is introduced below., Quality Control of 6-Chloro-4-methylpyridin-3-amine

Compound 6-chloro-4-methylpyridin-3-amine la (568 mg, 4.0 mmol), tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.22 g, 4.0 mmol), cesium carbonate (3.8 g, 12 mmol), [1,1′-bis(diphenylphosphine)ferrocene]palladium dichloride dichloromethane adduct (146 mg, 0.2 mmol), 1,4-dioxane (30 mL), and water (7 mL) were mixed, degassed, and heated to reflux under nitrogen for 16 hrs. The mixture was cooled to room temperature and concentrated to remove solvent under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 20/1 to 2/1) to produce the target compound tert-butyl 5-amino-4-methyl-5′,6′-dihydro-[2,3′-dipyridyl]-1′(2’H)-carboxylate 1b (401 mg, yellow oil), yield: 34%. MS m/z (ESI):290[M+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, 66909-38-4, 6-Chloro-4-methylpyridin-3-amine.

Reference:
Patent; Beijing InnoCare Pharma Tech Co., Ltd.; CHEN, Xiangyang; PANG, Yucheng; (44 pag.)EP3409672; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58539-65-4, 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. 58539-65-4, name is 2-Methylnicotinamide. A new synthetic method of this compound is introduced below.

Step 2 Preparation of 3-cyano-2-methylpyridine: To a suspension of 2-methylnicotinamide from step 1 (11.1 g, 0.081 mol) in triethylamine (24.8 g, 0.243 mol) and 400 mL of methylene chloride was added trifluoroacetic anhydride (21.0 g, 0.100 mol) rapidly at 0 C. The reaction was complete after a few minutes at this temperature. Water was added and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with water, brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated and the residue was purified by chromatography on silica gel (ethyl acetate/hexane, 1:1) to give 7.2 g of 3-cyano-2methylpyridine as a pale yellow solid (75%): mp(DSC) 56-58 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58539-65-4, 2-Methylnicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; GD Searle & Co; US5616601; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 120739-77-7, 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. 120739-77-7, name is N-((6-Chloropyridin-3-yl)methyl)ethanamine, molecular formula is C8H11ClN2, 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.

352.0 g of n-butyl acetate and 102.9 g of a 35% potassium carbonate aqueous solution were charged in a 1-L separable flask. The solution was cooled to 4C, 48.8 g of 1,1-dichloro-2-nitroethene (net weight 40.6 g) was added dropwise while stirring over 30 minutes, and 44.8 g of 2-chloro-5-(ethylaminomethyl)pyridine (net weight 44.4 g) was subsequently added dropwise over 3 hours. The reaction mixture was stirred at -4C for 15 minutes, 60.6 g of a 40% methyl amine solution was added dropwise over 3 hours, and the stirring was further continued for 4 hours. The obtained reaction mixture was warmed to 15C and extracted four times with 51.5 g, 40.3 g, 30.0 g, and 30.0 g of water, and the obtained four extracted aqueous layers were combined. The combined aqueous layer was extracted four times with 75.0 g of 5-ethyl-2-methylpiridine at 15C, and the obtained four extracted 5-ethyl-2-methylpyridine layers were combined (amount of the recovered aqueous layer 1, 247.8 g). After washing the combined 5-ethyl-2-methylpyridine layer with 50.0 g of a saturated sodium sulfate solution (amount of the recovered aqueous layer 2, 66.0 g), 800 g of n-heptane was added thereto and concentrated at 4.5 kPa, 25 to 35C until the amount of the residual solution was 345 g. 20.0 g of 5-ethyl-2-methylpyridine was added to the concentrated mass, and the mixture was maintained at 40C for 1 hour followed by filtration to remove insoluble matters. The obtained filtrate was flushed down with 10.0 g of 5-ethyl-2-methylpyridine to a 500-ml separable flask, the temperature was adjusted to 35C. Then 0.01 g of seed crystals of (1E)-N-[(6-chloro-3-pyridinyl)methyl]-N-ethyl-N’-methyl-2-nitro-1,1-ethenediamine was added and the mixture was cooled to 15C over 5 hours, and subsequently cooled at -10C over 10 hours for crystallization. The crystalline mass was further stirred at -10C for 3 hours and filtered (recovered filtrate amount, 304.1 g). The obtained crystals were washed with 300.0 g of n-butyl acetate which had been cooled to -10C (recovered washing amount, 305.9 g). The washed crystals were dried at 2.7 kPa, 40C for 4 hours to obtain 45.3 g of (1E)-N-[(6-chloro-3-pyridinyl)methyl]-N-ethyl-N’-methyl-2-nitro-1,1-ethenediamine at a content of 98.9%

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 120739-77-7, N-((6-Chloropyridin-3-yl)methyl)ethanamine.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2186802; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 86521-05-3, 2-((Trimethylsilyl)ethynyl)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 2-((Trimethylsilyl)ethynyl)pyridine, blongs to pyridine-derivatives compound. Safety of 2-((Trimethylsilyl)ethynyl)pyridine

2-Ethynyl-pyridineA solution of 2-trimethylsilanylethynyl-pyridine (3.05 g, 14 mmol) in MeOH (8.5 mL) was added dropwise to potassium hydroxide solution (1 N, 14 mL) and the reaction mixture was stirred at room temperature for 1 h and then acidified with HC1 (3 N, 8.5 mL) and the mixture concentrated. The residue was then diluted with water and make alkaline with solid sodium carbonate, extracted with diethyl ether and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, diethylether) afforded the title compound (1.3 g, 75%) as a brown liquid. MS: m/e = 176.0[M+H]+.

The synthetic route of 86521-05-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERNANDEZ, Maria-Clemencia; LUCAS, Matthew C.; THOMAS, Andrew; WO2012/62687; (2012); 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. 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, the common compound, a new synthetic route is introduced below. Safety of 3-(Trifluoromethyl)pyridine-2-carboxaldehyde

N-((6- Azaspiro[2.5]octan-l-yi)methyl)-6-(2-chioro-5-fluorophenyi)pyridazm-3-aniine hydrochloride salt (11 mg, 0.028 mmol) was suspended in DCM (1 raL) and 3-(trifluoromethyl)pyridine-2- carbaldehyde (24 mg, 0.14 mmol) was added and allowed to stir at r.t. for 5 min, after which time sodium triacetoxyborohydride (30 mg, 0.14 mmol) was added. The resulting solution was stirred at r.t. overnight, after which time the reaction mixture was quenched with sat. NaHCO-j, and extracted with 3: 1 chloroform/IP A. Organic extracts were filtered through a phase separator, and concentrated. Crude residue was purified by RP-HPLC, and fractions containing product were basified with sat. NaHCQs, and extracted with 3: 1 chloroform/IP A. Organic extracts were filtered through a phase separator and concentrated to give the title compound as a colorless oil (6.2 mg, 44%). -WJR (400 MHz, CDCI3) delta 8.80 (dd, J= 4.6, 0.8 Hz, 1H), 7.95 (dd, J = 8.0, 1.2 Hz, 1H), 7,61 (d, ./ 9.3 Hz, I I I). 7,48 (dd, J = 9:2, 3, 1 Hz, 1H), 7,41 (dd, ,/ 8.8, 5,0 Hz, 1 1 1). 7.31 (dd, J= 7.8, 4.8 Hz, 1H), 7,07 – 7.02 (m, 1 1 1). 6.68 (d, J= 9.3 Hz, H i). 4.83 (t, ./ 4.6 Hz, 1H), 3,83 (s, 2H), 3,52 – 3.41 (m, 2H), 2,67 – 2.62 (m, 2H), 2.50 – 2,45 (m, 21 1). 1.83 – 1,78 (m, 1H), 1,69 – 1.65 (m, I I I). 1 ,49 – 1 ,46 (m, 1 1 1). 1.25 – 1 ,20 (m, H i). 1.05 – 0,97 (m, IH), 0.61 (dd, J= 8.4, 4.6 Hz, IH), 0,28 (t, ,/ 4,9 Hz, H i), ES-MS [M+H]+ = 506.2,

The synthetic route of 131747-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig, W.; BRIDGES, Thomas, M.; CONN, P., Jeffrey; BENDER, Aaron, M.; ENGERS, Darren, W.; (130 pag.)WO2019/14427; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 65873-72-5, 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. 65873-72-5, name is 6-Methoxynicotinaldehyde, molecular formula is C7H7NO2, 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.

EXAMPLE 25 : 1-(3,4-Difluorobenzyl)-5-(phenoxymethyl)pyridin-2(1H)-one (Final Compound 16-03) ;Step 1 : (6-Methoxypyridin-3-yl)methanol According to Scheme 16 Method A: A solution of 6-methoxynicotinaldehyde (leq, 2.19mmol, 0.30g) and LiAlH4 (0.5eq, 1.05mmol, 0.04g) in THF (10mL) was stirred for 30 min. at 0C and overnight at room temperature. After the addition of AcOEt, the reaction mixture was diluted with water. The organic layer was washed with saturated NH4Cl solution, dried over Na2SO4, filtered and evaporated. The resulting crude residue was purified by silica gel chromatography (AIT Flashsmart prepacked column 25g SiO2) using CH2Cl2/AcOEt 80/20 to afford (6-methoxypyridin-3-yl)methanol (1.80mmol, 0.26g, 90%) as a pale oil. LC (XTerra RP18, 3.5mum, 3.0x50mm Column): RT = 1.86min; MS m/z (CI) [MH]+= 140.

According to the analysis of related databases, 65873-72-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; ADDEX PHARMACEUTICALS S.A.; WO2006/30032; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1095823-39-4, 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 1095823-39-4, name is 5-Chloro-4-(trifluoromethyl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A 20 mL vial was charged with compound A.5 (191.8 mg, 0.0006561 mol), methylene chloride (3.0 mL), a 2.0 M solution of oxalyl chloride in methylene chloride (390 muL) and DMF (10.0 muL, 0.000129 mol). The reaction mixture was stirred for 15 minutes at rt, then concentrated in vacuo and the resultant residue was taken up in acetonitrile (3.0 mL). To this solution was added a solution of compound A.6 (129 mg, 0.000656 mol) and pyridine (0.5 mL, 0.006 mol) in acetonitrile (1.5 mL). The reaction mixture was stirred at RT overnight. The solvent was removed under reduced pressure, and the residue was purified by combiflash (0-30% EtOAc/CH2Cl2) to give compound A.7 in 49% yield. LCMS: m/z 471 [M+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 1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2009/36419; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem