Tag: M.W:100-200

Synthetic Route of 74976-31-1, Adding some certain compound to certain chemical reactions, such as: 74976-31-1, name is 6-Chloro-1H-pyrrolo[3,2-c]pyridine,molecular formula is C7H5ClN2, 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 74976-31-1.

To a solution of6-chloro-1H-pyrrolo[3,2-c]pyridine (5.00 g, 32.8 mmol) in DMF(20 mL) was added NaH (1.57 g, 39.3 mmol) at 0C. The reaction mixture was stirred for1 h, then SEM-Cl (6.56 g, 39.3 mmol) was added at 0C. The reaction mixture wasstirred at room temperature for 1 h, then quenched with HzO (100 mL) and extracted withDCM (3 x 100 mL). The organic layer was separated and washed with brine (3 x 10025 mL), then dried over anhydrous NazS04 and concentrated in vacuo. The crude materialwas purified by column chromatography (10-15% EtOAc in hexanes) to afford the titlecompound (7.00 g, 75%) as a yellow oil. DH (400 MHz, CD30D) -0.07 (s, 9H), 0.87 (t, J7.83 Hz, 2H), 3.52 (t, J7.83 Hz, 2H), 5.57 (s, 2H), 6.71 (d, J2.93 Hz, 1H), 7.50 (d, J3.42Hz, 1H), 7.64 (s, 1H), 8.61 (s, 1H). HPLC-MS (method 6): MH+ m/z 283.3, RT 2.1230 minutes.

According to the analysis of related databases, 74976-31-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHAPPELL, Rose Elizabeth; DEBOVES, Herve Jean Claude; FOLEY, Anne Marie; FOULKES, Gregory; JONES, Elizabeth Pearl; LECOMTE, Fabien Claude; QUINCEY, Joanna Rachel; SCHULZE, Monika-Sarah Elisabeth Dorothea; SELBY, Matthew Duncan; SMALLEY, Adam Peter; TAYLOR, Richard David; TOWNSEND, Robert James; ZHU, Zhaoning; (278 pag.)WO2018/229079; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13534-97-9, Adding some certain compound to certain chemical reactions, such as: 13534-97-9, name is 6-Bromopyridin-3-amine,molecular formula is C5H5BrN2, 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 13534-97-9.

Example 1; Preparation of intermediates N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(2-hydroxypropan-2-yl)benzamide (1D) and N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(trifluoromethyl)benzamide (1E); Step A: Commercially available 6-bromopyridin-3-amine (1A, 20 g, 1.0 equivalent) was added in portions to a solution of potassium thiocyanate (5.0 equivalents) in acetic acid (0.4 M) at -5° C. After addition, the mixture was cooled to -15° C., and a solution of Br2 (1.3 equivalent) in acetic acic (9.4 M) was added drop wise via an additional funnel. The mixture was then warmed to room temperature and stirred for 12 h. The resulting precipitate was filtered; 100 mL EtOAc and 200 mL H2O were added to the filtrate and then 200 mL of solvent was removed in vacuo. The residue was stirred in ice bath for 10 minutes, and then the resulting precipitate was collected by filtration and washed twice with cold 10percent MeOH in Et2O. The filtrate was concentrated and the product was crystallized in ice bath to obtain a second crop of product after washing twice with cold 10percent MeOH in Et2O. The product 1B (77percent) was obtained as a brown solid after drying under vacuum, and then used without further purification. 1H NMR (400 MHz, DMSO-d6) delta ppm 4.94 (br. s., 1H) 7.44 (d, J=8.34 Hz, 1H) 7.57 (d, J=8.34 Hz, 1H) 8.04 (br. s., 1H); ESI-MS: m/z 230.0 (M+H)+.

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. 13534-97-9, 6-Bromopyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/318425; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 75903-58-1, 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. 75903-58-1, name is 6-Aminopyridine-2-sulfonamide, molecular formula is C5H7N3O2S, 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.

[001308] 2-Chloro-6-(3-fluoro-5-isobutoxy-phenyl)pyridine-3-carboxylic acid (3.00 g, 9.27 mmol) was dissolved in N,N-dimethylformamide (30.00 mL), and 1,1?- carbonyldiimidazole (2.254 g, 13.90 mmol) was added to the solution. The solution was allowed to stir at 65 C for 1 hour. In a separate flask, sodium hydride (444.8 mg, 11.12 mmol) was added to a solution of 6-aminopyridine-2-sulfonamide (1.926 g, 11.12 mmol) in N,N-dimethylformamide (15.00 mL). This mixture was stirred for one hour before being added to the prior reaction mixture. The final reaction mixture was stirred at 65 C for 15 minutes. Volatiles were removed under reduced pressure. The remaining oil was taken up in ethyl acetate and washed with aqueous hydrochloric acid (1 N, 1 × 75 mL) and brine (3 × 75 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The remaining white solid (4.7 g) was fully dissolved in isopropanol (120 mL) in an 85 C water bath. The colorless solution was allowed to slowly cool to room temperature with slow stirring over 16 hours. The crystalline solids that had formed were collected by vacuum filtration, and then rinsed with cold isopropanol (50 mL). Upon drying, N-[(6-amino-2- pyridyl)sulfonyl]-2-chloro-6-(3-fluoro-5-isobutoxy-phenyl)pyridine-3-carboxamide (3.24 g, 6.76 mmol, 73%) was obtained as a white solid. 1H NMR (400 MHz, DMSO- d6) delta 12.78 (s, 1H), 8.15 (d, J = 8.0 Hz, 1H), 8.09 (d, J = 7.9 Hz, 1H), 7.73 – 7.63 (m, 1H), 7.49 (dd, J = 8.6, 1.9 Hz, 2H), 7.21 (d, J = 7.3 Hz, 1H), 6.99 (dt, J = 10.7, 2.2 Hz, 1H), 6.74 (d, J = 8.4 Hz, 1H), 6.64 (s, 2H), 3.86 (d, J = 6.5 Hz, 2H), 2.05 (dp, J = 13.3, 6.5 Hz, 1H), 1.02 (dd, J = 12.7, 6.4 Hz, 6H).

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 75903-58-1, 6-Aminopyridine-2-sulfonamide.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BEAR, Brian; CLEMENS, Jeremy; CLEVELAND, Thomas; COON, Timothy, Richard; GROOTENHUIS, Peter, Diederik Jan; FRIEMAN, Bryan, A.; HADIDA RUAH, Sara S.; KHATUYA, Haripada; KRENITSKY, Paul, J.; MILLER, Mark, Thomas; SILINA, Alina; UY, Johnny; ZHOU, Jinglan; (528 pag.)WO2017/173274; (2017); 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.24484-93-3, name is Methyl 4-chloropicolinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Computed Properties of C7H6ClNO2

(Production Example 22) 4-(4-Amino-2-fluorophenoxy)pyridine-2-carboxylic acid methyl ester dihydrochloride 4-Chloropyridine-2-carboxylic acid methyl ester (30 g) and 2-fluoro-4-nitrophenol (41.2 g) were dissolved in chlorobenzene (24 ml), followed by stirring under a nitrogen atmosphere at 120 C for 4 hr. The reaction mixture was allowed to cool down to room temperature, methanol (100 ml) was added, and stirred for 30 min. The solvent was removed under reduced pressure, then the resultant residue was partitioned between ethyl acetate (300 ml) and a 1N aqueous solution of sodium hydroxide (150 ml). The separated organic layer was washed with a 1N aqueous solution of sodium hydroxide (100 ml) and brine (150 ml) and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, ethanol (200 ml) was added to the resultant residue, followed by stirring for 30 min. The solid was collected by filtration and the filtrate was purified by silica gel column chromatography (YMC, SIL-60-400/230W, eluent; heptane:ethyl acetate = 1:1). Fractions containing the target compound were concentrated under reduced pressure, the resultant solid was combined to the solid above to provide 4-(2-fluoro-4-nitrophenoxy)pyridine-2-carboxylic acid methyl ester as a pale brown solid (20.0 g, 40.0 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24484-93-3, Methyl 4-chloropicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1889836; (2008); 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. 54221-95-3, name is 2-Acetylaminoisonicotinic acid. A new synthetic method of this compound is introduced below., Product Details of 54221-95-3

(C) Ethyl 2-aminoisonicotinate 2-(Acetylamino)isonicotinic acid (13 g, 73.60 mmol) synthesised by the method of Example 7, (A) was added with ethanol (50 ml) and toluene (150 ml) and heated to 100-110 C. The mixture was added dropwise with concentrated sulfuric acid (7 ml) and heated for 11 hour with stirring. The reaction solution was returned to room temperature and poured into saturated aqueous sodium hydrogencarbonate cooled with ice. The mixture was extracted with chloroform and the collected organic layer was dried over magnesium sulfate and concentrated under reduced pressure to obtain 7.6 g (23% for the two steps) of the title compound as pale yellow crystals without purification. 1H-NMR (CDCl3) delta: 1.39 (3H, t, J=7.07 Hz), 4.37 (2H, qu, J=7.07 Hz), 4.63 (2H, brd), 7.07 (1H, s), 7.17 (1H, dd, J=0.98, 5.12 Hz), 8.18 (1H, d, J=5.12 Hz) EI/MS; m/z: 165 (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, 54221-95-3, 2-Acetylaminoisonicotinic acid.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD; US2003/92720; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 7584-05-6, Adding some certain compound to certain chemical reactions, such as: 7584-05-6, name is 3-Methylisonicotinonitrile,molecular formula is C7H6N2, 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 7584-05-6.

To a stirred solution of 3-methylisonicotinonitrile (5.00 g, 42.30 mmol) in DCM(100 mL)was added 3chioroperoxybenzoic acid (14.61 g, 85.00 nimol) at 0 C and stirred at ambienttemperature for 16 h. The reaction mixture was diluted with water (50 mL), basified with 10 % NaHCO3 and extracted with ethyl acetate (2 x 75 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate and evaporated under reduced pressure to obtain Intermediate 24A (3.50 g, 61.30%) as a pale yellow solid. ?HNIVR (400 MHz, DMSOd6) oe ppm 2.38 (s, 3 H), 7.84 7.85 (d, .1= 6.8 Hz, 1 H), 8.21 8.23 (dd, J= 1.2 Hz, 6.8 Hz, IH),8.41 (s, 1H). LCMS MethodD): retention time 0.44 mm, [M+H1 135.2.

According to the analysis of related databases, 7584-05-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6980-08-1 , The common heterocyclic compound, 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine, molecular formula is C5H4ClN3O2, 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) Diethyl 2-(2-amino-3-nitropyridin-4-yl)malonate (A 132) NaH (60% dispersion in mineral oil, 0.830 g, 20.7 mmol) was added to a solution of diethyl malonate (3.16 ml_, 20.7 mmol) in NMP (50 ml_) and the resulting solution was stirred at room temperature for 10 minutes. 4-Chloro-3-nitropyridin-2-amine A14 (1.00 g, 5.76 mmol) was then added and the mixture heated at 50 C for 2 hours. The mixture was cooled to room temperature and diluted with EtOAc (250 ml_) and water (100 ml_). The organic layer was separated and washed with water (100 ml_) followed by brine (100 ml_). This process was repeated three times before the organic layer was dried (Na2S04), filtered and the filtrate concentrated under reduced pressure to give a yellow oil which was purified by silica gel column chromatography (40 g Si02 cartridge, 0-100% EtOAc in petroleum benzine 40-60 C) to give the title compound as a yellow solid (1.69 g, 99%). H NMR (400 MHz, ck-DMSO) delta 8.28 (d, J = 4.9 Hz, 1 H), 7.53 (s, 2H), 6.58 (d, J = 5.0 Hz, 1 H), 5.20 (s, 1 H), 4.18 (qd, J = 7.1 , 0.9 Hz, 4H), 1.18 (t, J = 7.1 Hz, 6H). LCMS-B: rt 3.20 min, m/z (positive ion) 298 [M+H]+.

The synthetic route of 6980-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; STUPPLE, Paul Anthony; WALKER, Scott Raymond; PINSON, Jo-Anne; LAGIAKOS, Helen Rachel; LUNNISS, Gillian Elizabeth; HOLMES, Ian Peter; STUPPLE, Alexandra Elizabeth; BERGMAN, Ylva Elisabet; FOITZIK, Richard Charles; KERSTEN, Wilhelmus Johannes Antonius; CAMERINO, Michelle Ang; WO2014/128465; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1824-81-3, 2-Amino-6-picoline, 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, HPLC of Formula: C6H8N2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H8N2

(1) 200 mL of acetic anhydride was added to 39.9 g of 2-amino-6-methylpyridine at room temperature, and the mixture was stirred at 70C for 2 hours. The obtained reaction solution was concentrated, neutralized with an aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic phase was washed with saturated brine. Subsequently, the organic phase was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated to obtain 60.6 g of an acetamide product [149-1] as follows. [Show Image] The spectral data of the compound represented by the above Formula [149-1] is presented below. 1H-NMR (CDCl3) delta: 8.10 (1H, brs), 7.97 (1H, d, J=8.0 Hz), 7.57 (1H, t, J=8.0 Hz), 6.88 (1H, d, J=8.0 Hz), 2.43 (3H, s), 2.17 (3H, s). mass: 151 (M+1)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1824-81-3, 2-Amino-6-picoline, and friends who are interested can also refer to it.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1754706; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19337-97-4, 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.19337-97-4, name is trans-3-(3-Pyridyl)acrylic acid, molecular formula is C8H7NO2, molecular weight is 149.15, as common compound, the synthetic route is as follows.

General procedure: Compound 1c-9c (1.0mmol) was dissolved in anhydrous tetrahydrofuran (20mL). To the solution, triethylamine (1.2mmol) was slowly added and the solution was cooled to-20C, pivaloyl chloride (1.2mmol) was then added, and the reaction mixture was stirred for about 45min. Next, the compound 13 or 15 and n-butyllithium were added to the reaction solution and stirred for 1h, checked for product formation via TLC. Then saturated aqueous solution of ammonium chloride (10mL) was added to quench the n-butyllithium in the reaction and extracted with ethyl acetate, the organic phase was washed with saturated brine (30mL×3), Dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (PE/EA=3: 1) to afford 1-9.

Statistics shows that 19337-97-4 is playing an increasingly important role. we look forward to future research findings about trans-3-(3-Pyridyl)acrylic acid.

Reference:
Article; Zou, Yu; Yan, Chang; Zhang, Huibin; Xu, Jinyi; Zhang, Dayong; Huang, Zhangjian; Zhang, Yihua; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 313 – 319;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 40381-90-6, 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 40381-90-6, name is 2,6-Dichloropyridine-3-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 2,6-dichioronicotinonitrile (050 g, 2.89 mmoi) in MeOH (10 mL)was added sodium methanolate (0.62 g, 2.89 mmol) at ambient temperature. The reactionmixture was stirred at 60 C for 12 h. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure, diluted with water (40 ml) and extracted with ethyl acetate (2 x 75 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by preparativeHPLC [Xbridge Phenyl (21.2 x 250 ID) 5 micron; Solvent A: 0.1% TFA, Solvent B:Acetonitrile, Gradient: 5-25% B over 25 mm, Flow: 20 mL/minj to 23A (0.48 g, 19%) as an off white solid. ?HNMR (400 MHz, CDCI3) ppm 4.08 (s, 3 H). 7.01 — 7.03 (d, J= 7.2 Hz, I H), 7.80 7.82 (s, J= 8.0 Hz, IH). LCMS MethodD): retention time 1.94 mm, [M+H] 169.2.

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 40381-90-6, 2,6-Dichloropyridine-3-carbonitrile.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem