Tag: M.W:100-200

Application of 120739-77-7 ,Some common heterocyclic compound, 120739-77-7, molecular formula is C8H11ClN2, 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.

In a 100 mL three neck round bottom flask, 17.0 g (0.1 mol) of N-(6-chloropyridine-3-methylene)ethylamine, 15.0 g (0.09 mol) of 1,1-dimethylthio-2-nitroethylene, and 50 mL of absolute ethanol were added. Heated to reflux. Reflux for 8h. Stop reflow, cooled to room temperature. Concentrated to viscous liquid. Silica gel column chromatography (dichloromethane: acetone = 5: 1 (v / v)) gave the product 6.5 g (compound IV-1) in a yield of 23%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,120739-77-7, its application will become more common.

Reference:
Patent; East China University of Science and Technology; Li, Zhong; Xu, Xiaoyong; Yuan, Zihao; Lu, Siyuan; Shao, Xusheng; Xu, Zhiping; (66 pag.)CN105669660; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 131747-62-1, 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 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Sodium triacetoxyborohydride (40 mg, 0.19 mmol) was added to a solution of (3-((1- amino-2,3-dihydro-1 H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol (30 mg, 0.093) and 3-trifluoromethyl-2-formylpyridine (15 mg, 0.086 mmol) in DCM (1 ml_). The reaction was stirred at rt for 24 h before aq. sat. NaHCO3 (2 ml.) was added to the mixture was filtered over a phase separator. The organic filtrate was evaporated to dryness in a Genevac. The crude material was purified by prep. LCMS to afford the title compound (18.9 mg, 42.1 %). MS (ESI) : m/z [M + H]+ 481.2

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 131747-62-1, 3-(Trifluoromethyl)pyridine-2-carboxaldehyde.

Reference:
Patent; N.V. Organon; GILLEN, Kevin James; GILLESPIE, Jonathan; JAMIESON, Craig; MACLEAN, John Kinnaird Ferguson; MOIR, Elizabeth Margaret; RANKOVIC, Zoran; WO2010/115952; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 113209-90-8 ,Some common heterocyclic compound, 113209-90-8, molecular formula is C6H5ClFNO, 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.

A mixture of 6′-[3-(dimethylamino)-1-pyrrolidinyl]-4-hydroxy-2/-/-1 ,3′-bipyridin-2-one (150 mg, 0.499 mmol) and triphenylphosphine (327 mg, 1.249 mmol) was treated with (4-chloro-5-fluoro-2-pyridinyl)methanol (81 mg, 0.499 mmol) dissolved in dichloromethane (5 ml). Bis(1 ,1-dimethylethyl) (E)-1 ,2-diazenedicarboxylate (287 mg, 1.249 mmol) was added in two portions, and the reaction mixture was stirred at 250C for 2 h then concentrated under a stream of nitrogen gas. Purification by reverse phase HPLC (1 to 50% gradient) and concentration of the fractions containing product provided a residue. The residue was treated with aqueous NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to provide the title compound as a white solid (1 14 mg, 51 %): 1H NMR (400 MHz, CDCI3) delta ppm 8.46 (s, 1 H), 8.06 (d, J = 2.7 Hz, 1 H), 7.56-7.48 (m, 2 H), 7.21 (d, J = 7.6 Hz, 1 H), 6.43 (d, J = 9.0 Hz, 1 H), 6.09 (dd, J = 7.4, 2.5 Hz, 1 H), 5.98 (d, J = 2.7 Hz, 1 H), 5.10 (s, 2 H), 3.95-3.84 (m, 1 H), 3.77-3.65 (br m, 2H), 3.55-3.22 (br m, 2 H), 2.60 (br s, 6 H), 2.47-2.29 (br m, 2 H); ES-LCMS m/z 444 {M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113209-90-8, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/76387; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 61494-55-1, 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid, molecular formula is C7H6ClNO2, 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.

To a stirred solution of diisopropyl amine (0.82 mL, 5.8 mmol) in anhydrous THF (5 mL) cooled to -15C was added n-butyl lithium (2.5 M in hexanes, 2.3 mL, 5.8 mmol) slowly, maintaining the temperature of the flask between -10C and 0C. The resultant mixture was stirred at room temperature for 15 minutes before being cooling to 0C. The LDA thus formed was added to a rapidly stirred suspension of 2-(2-chloropyridin-3-yl)acetic acid (500 mg, 2.9 mmol) in anhydrous THF (10 mL) at 0C. The resultant bright yellow suspension was stirred at 0C for 15 min. A solution of 2-fluoro-4-iodo-l -isothiocyanatobenzene (814 mg, 2.9 mmol) in anhydrous THF (10 mL) was then added to the reaction mixture (brown suspension) and heated to 65C for 18 hours. The reaction mixture was cooled and the volatiles removed in vacuo. The resultant crude product was redissolved in THF, cooled to 0C and 10% aqueous acetic acid in water (10 mL) was added slowly. Acetonitrile (5 mL) was added slowly until a brown solid developed, the solid was isolated by filtration and washed with ether and acetonitrile to give the title compound. LC/MS: [M+l]+ 415; NMR (300 MHz, DMSO-d6): d 10.74 (s, 1H), 9.21 (s, 1H), 8.36-8.25 (m, 2H), 7.79 (d, J = 1.8 Hz, 1H), 7.68-7.61 (m, 1H), 7.51 (t, J=8.5 Hz, 1H), 7.42- 7.31 (m, 1H).

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 61494-55-1, 2-(2-Chloropyridin-3-yl)acetic acid.

Reference:
Patent; NFLECTION THERAPEUTICS, INC.; KINCAID, John; NEWSAM, John; KISAK, Edward; WOOTTON, Michael; KUSHWAHA, Avadhesh; (364 pag.)WO2020/106304; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 19346-44-2, name is 2-Fluoro-3-nitro-5-methylpyridine, molecular formula is C6H5FN2O2, 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. Quality Control of 2-Fluoro-3-nitro-5-methylpyridine

General procedure: The dimethyl derivatives (4,4?, 5,5? or 6,6?) of 3,3?-dinitro-2,2?-azobipyridine were synthesized from the respective hydrazo-derivatives obtained previously from 3-nitro-4(or 5 or 6)-methyl-2-hydrazine-pyridine, respectively. Syntheses of these hydrazo derivatives were very similar to the synthesis of 3,3?-dinitro-2,2?-hydrazobipyridine. Instead of ethanol n-propanol was used and its mixtures were heated at boiling temperature for 30 min in the water bath. 2.52 g (0.015 mol) of 3-nitro-4(or 5 or 6)-methyl-2-hydrazine-pyridine were used to synthesis. The synthesized red-brown needle-like crystals of 4,4?-dimethyl-3,3?-dinitro-2,2?-hydrazobipyridine melt with decomposition at 255C. The yield was 53.1%. The synthesized brown needle-like crystals of 5,5?-dimethyl-3,3?-dinitro-2,2?-hydrazobipyridine melt with decomposition at 285C. The yield was 54.0%. The synthesized dark-brown needle-like crystals of 6,6?-dimethyl-3,3?-dinitro-2,2?-hydrazobipyridine melt with decomposition at 275C. The yield was 51.0%. 1 g of the obtained in this way 4,4?(or 5,5? or 6,6?)-3,3?-dinitro-2,2?-hydrazobipyridine was used to obtain respective azo derivatives in the same way as 3NAP. The synthesized orange needle-like crystals of 4,4?-dimethyl-3,3?-dinitro-2,2?-azobipyridine (4M3NAP) melt with decomposition at 260C. The yield was 74.2%. The synthesized orange needle-like crystals of 5,5?-dimethyl-3,3?-dinitro-2,2?-azobipyridine (5M3NAP) melt with decomposition at 256C. The yield was 77.1%. The synthesized orange powder of 6,6?-dimethyl-3,3?-dinitro-2,2?-azobipyridine (6M3NAP) melt with decomposition at 206C. The yield was 80.3% [51,52,54].

With the rapid development of chemical substances, we look forward to future research findings about 19346-44-2.

Reference:
Article; Kucharska; Hanuza; Lorenc; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 127; (2014); p. 370 – 380;,
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. 19235-89-3, name is 4-Chloropyridine-2-carbonitrile, the common compound, a new synthetic route is introduced below. Formula: C6H3ClN2

[Referential Example 114]; 4-Methylthiopyridine-2-carbonitrile; Sodium thiomethoxide (1.01 g) was added to 4-chloropyridine-2-carbonitrile (2.00 g) obtained from Referential Example 113 in N,N-dimethylformamide (20 mL) at 0C, followed by stirring for 2 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (hexane – ethyl acetate), to thereby give the title compound as a solid (1.96 g, 90%).1H-NMR(400MHz,CDCl3)delta: 2.53(3H,s), 7.26-7.27(1H,m), 7.45-7.46(1H,m), 8.45-8.46(1H,m). MS(EI)m/z: 150(M+) .

The synthetic route of 19235-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1591443; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14916-65-5, 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. 14916-65-5, name is 6-Nitropyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 6-nitro-pyridin-3-ylamine (50 mg, 0.33 mmol) in DMF (3 mL) was added NaH (60% in mineral oil, 25 mg, 0.66 mmol), and the mixture was stirred at r.t for 30 min. Then 5-bromo-2-methoxy-benzenesulfonyl chloride (86 mg, 0.3 mmol) was added and the mixture was stirred at 50 C overnight. TLC showed that the reaction was complete. The resultant was concentrated in vacuum to remove DMF. The residue was diluted with DCM (30 mL) and the mixture was washed with IN HC1 (30 mL x3) .The organic layer dried over Na2S04 and concentrated to dryness in vacuum. The residue was purified by silica gel column (PE/EtOAc, 1/1) to give 30 mg (yield: 26%) of 5-bromo-2-methoxy-N-(6-nitro-pyridin-3-yl)- benzenesulfonamide as a brown solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14916-65-5, 6-Nitropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; DAHL, Russell; COSFORD, Nicholas, D.P.; MILLAN, Jose, Luis; WO2013/126608; (2013); 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.184416-83-9, name is 2,3-Dichloropyridin-4-amine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.HPLC of Formula: C5H4Cl2N2

A mixture of tert-butyl ((l S)-l’-(3-iodo-l-(tetrahydro-2H-pyran-2-yl)-lH- pyrazolo[3,4-b]pyrazin-6-yl)-l,3-dihydrospiro[indene-2,4′-piperidin]-l-yl)carbamate (350.0 mg, 555.0 pmol, from Intermediate J), 2,3-dichloropyridin-4-amine (135.0 mg, 832.0 pmol, CAS 184416-83-9), XantPhos-Pd-G4 (47.6 mg, 55.4 pmol) and Cs2C03 (270.0 mg, 832.0 pmol) in PhMe (10 mL) was stirred at 100 C for 12 hours. The reaction mixture was concentrated and purified by silica gel column (EtOAc in petroleum ether = 0-30%) to give tert-butyl N-[(3S)-l’-{3-[(2,3-dichloropyridin-4-yl)amino]-l-(oxan-2-yl)-lH-pyrazolo[3,4- b]pyrazin-6-yl}-l,3-dihydrospiro[indene-2,4′-piperidin]-3-yl]carbamate (200.0 mg, 54% yield) as a yellow solid. LCMS m/z [M+H]+ = 665.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,184416-83-9, 2,3-Dichloropyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 75279-39-9, N-(4-Aminopyridin-2-yl)acetamide, 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, Product Details of 75279-39-9, blongs to pyridine-derivatives compound. Product Details of 75279-39-9

Immediately add 45% HBF4 water to solid compound d obtained by rotary evaporation of the above solutionSolution (600mL, 10.8mo1),After stirring, the solid was completely dissolved and ethanol (200 mL) was added.Ice salt bath cooled to below -5C,Isoamyl nitrite (150 mL, 1.12 mol) was added dropwise.Control temperature does not exceed 0 C,And stir the reaction below 0C for 3h.After the reaction was completed, tetrahydrofuran (200 mL) was added.Cool to below 0C,Suction filtrationThe solid was washed twice with tetrahydrofuran (20 mL) and dried in a vacuum desiccator to obtain a solid compound e (213.25 g, 85.3%) with a purity of 96%.The diazonium fluoborate (250g, 1mo1) was put into a dry 1L triple reaction flask.Heat to 120C,Solid decomposition,White smoke emerged from the reaction flask.Continue heating to exhaust white smoke.Solid decomposition is complete.Prepare a 40% NaOH solution (300 mL)The solids on the condenser tube are washed into the reaction flask.Heat reflux,As the product is sublimated,The continuous condensation of solids on the condenserCollect the solids,Repeat the above operation,2-amino-4-fluoropyridine (70 g, 62.5%) was obtained,98% purity.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75279-39-9, N-(4-Aminopyridin-2-yl)acetamide, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Lingkai Pharmaceutical Technology Co., Ltd.; Lu Qian; (7 pag.)CN107759515; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 902837-42-7, 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.902837-42-7, name is 7-Bromo-1H-pyrrolo[3,2-c]pyridine, molecular formula is C7H5BrN2, molecular weight is 197.032, as common compound, the synthetic route is as follows.

Sodium hydride (0.25 g, 6.2 mmol) is added under ice bath cooling to a mixture of 7-bromo-1H-pyrrolo[3,2-c]pyridine (0.8 g, 4.1 mmol) in DMF (10 ml). The mixture is stirred for 30 minutes before methyl iodide (0.25 ml, 4.1 mmol) is added. The mixture is warmed to RT and stirred for 17 h. The mixture is diluted with DCM and extracted with a saturated aqueous sodium hydrogencarbonate solution. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 0.61 g (71%). HPLC-MS: tR=0.88 min (METHOD-1).

Statistics shows that 902837-42-7 is playing an increasingly important role. we look forward to future research findings about 7-Bromo-1H-pyrrolo[3,2-c]pyridine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; US2015/57286; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem