Day: September 29, 2021

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

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 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

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. 59786-31-1, name is Methyl 3-bromoisonicotinate. A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-bromoisonicotinate

Example 55 Synthesis of (S)-N-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)-3-(5-methylfuran-2-yl)isonicotinamide Compound 106a. To a stirred solution methyl 3-bromoisonicotinate (0.300 g, 1.4 mmol, 1.0 equiv) in Dioxan (5 mL) and water (5 mL), was added (5-methylfuran-2-yl)boronic acid (0.212 g, 1.68 mmol, 1.2 equiv), Na2CO3 (0.297 g, 2.8 mmol, 2.0 equiv) and aerated the reaction mixture with nitrogen for 15 min and added Dichlorobis(triphenylphosphine)palladium(II) (0.098 g, 0.14 mmol, 0.1 equiv). Aerated the reaction mixture again with nitrogen for 15 min. The mixture was allowed to stir at 100 C. for 2 h. Product formation was confirmed by LCMS. The reaction mixture was diluted with water (50 mL) and washed with ethyl acetate (20 mL*2). Aqueous layer was separated and freeze dried over lyophilizer to obtain 3-(5-methylfuran-2-yl)isonicotinic acid (0.250 g).

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, 59786-31-1, Methyl 3-bromoisonicotinate.

Reference:
Patent; Praxis Biotech LLC; ALFARO, Jennifer; BELMAR, Sebastian; BERNALES, Sebastian; PUJALA, Brahmam; PANPATIL, Dayanand; BHATT, Bhawana; US2019/185451; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 76006-08-1 , The common heterocyclic compound, 76006-08-1, name is 5-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, 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 5-chloro-lH-pyrazolo[3,4-c]pyridine (130 mg, 0.847 mmol) dissolved in N,N-dimethylformamide (5.00 ml) was added cesium carbonate (579 mg, 1.778 mmol) followed by tert-butyl 4-((methylsulfonyl)oxy)-2-oxopiperidine-l-carboxylate (273 mg, 0.931 mmol). The reaction mixture stirred at room temperature overnight. LC/MS analysis indicated that the desired product was not obtained. The reaction was heated to 65C and stirred overnight. The mixture was filtered through a 0.2 mm Millex syringe-driven filter unit, washed with methanol (2 x 6 mL) and concentrated to dryness under reduced pressure. The crude mixture was purified by reverse phase HPLC (10% to 90% AcetonitrileAVater + 0.1% TFA, over 10 minutes) to provide the desired product tert-butyl 4-(5-chloro-lH-pyrazolo[3,4-c]pyridin-l- yl)-2-oxopiperidine-l -carboxylate. LCMS (ESI) calc’d for C16H19CIN4O3 [M+H]+ = 351, found 351

The synthetic route of 76006-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SILIPHAIVANH, Phieng; METHOT, Joey; LIPFORD, Kathryn Ann; MOLINARI, Danielle; SLOMAN, David, L.; WITTER, David; ZHOU, Hua; BOYCE, Christopher; HUANG, Xianhai; LIM, Jongwon; GUERIN, David; KARUNAKARAN, Ganesh Babu; BAKSHI, Raman Kumar; LIU, Ziping; FU, Jianmin; WAN, Zhilong; LIU, Wei; (216 pag.)WO2016/100050; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53937-02-3, 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 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone. This compound has unique chemical properties. The synthetic route is as follows.

Example 2Preparation of 4-(Benzyloxy)-l-(l-(2-morpholinoethyl)-li/-indazol-5-yl)pyridin-2(liJ)- one hydrochloridea) 4-(Benzyloxy)- 1 -(3 -methyl-4-nitrophenyl)pyridin-2( Ii7)-one; Chemical Formula: C19H16N2O4Exact Mass: 336.11 Molecular Weight: 336.34[0083] To a solution of 5-fluoro-2-mtrotoluene (1.00 g, 6.44 mmol) in DMF (6.5 mL) was added 4-benzyloxy-pyridin-2(lH)-one (1 11 g, 5.55 mmol) and Na2CO3 (0.588 g, 5.55 mmol). After stirring at 12O0C for 56 hours, the reaction mixture was cooled, and the solids were collected by filtration and washed with EtOAc (100 ml) and H2O (100 mL). The solids were triturated with hot H2O (50 mL) and then washed with Et2O (50 mL) to yield the title compound (0.94 g, 50%) as a light yellow solid: 1H NMR (500 MHz, DMSO-^6) delta 8.08 (d, J= 8.5 Hz, IH), 7.64 (d, J= 8.5 Hz, IH), 7.58 (d, J= 2.0 Hz, IH), 7.50 (dd, J = 9.0, 2.5 Hz, IH), 7.47-7.37 (m, 5H), 6.16 (dd, J = 8.0, 3.0 Hz, IH), 6.01 (d, J= 2.5 Hz, IH), 5 15 (s, 2H), 2.55 (s, 3H); ESI MS m/z 337 [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 53937-02-3, 4-Benzyloxy-2-(1H)-pyridone.

Reference:
Patent; AMR TECHNOLOGY, INC.; WO2008/86404; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 890302-02-0, 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 890302-02-0, name is 2-amino-6-(Trifluoromethyl)nicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

difluorophenyl)propanoic acid (0.731 g, 2.426 mmol) in DCM (32 mL) was added N- methylmorpholine (0.670 mL, 6.06 mmol) followed by isobutyl chloroformate (0.640 mL, 4.85 mmol). The reaction was then cooled to -20 C (IPA/dry ice) and 2-amino-6- (trifluoromethyl)nicotinic acid (0.50 g, 2.43 mmol) was added. The reaction slurry was allowed to slowly warm to ambient temperature overnight as bath thawed for 18 h. The reaction was heated to reflux for 2 h. Upon cooling to ambient temperature, the reaction was filtered. The filtrate was diluted with EtOAc. The organic layer was washed with saturated sodium bicarbonate, brine, dried (Na2S04) and concentrated in vacuo. The crude product was triturated with hexanes and filtered to give the product which was a mixture due to some racemization as an orange solid (0.41 g, used as is). NMR (500 MHz, CDC ) delta 8.80 – 8.75 (m, 1H), 7.95 – 7.89 (m, 1H), 6.74 – 6.71 (m, 3H), 5.52 – 5.44 (m, 1H), 5.08 – 5.01 (m, 1H), 3.44 – 3.37 (m, 1H), 3.19 – 3.15 (m, 1H), 1.47 – 1.44 (m, 9H)

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 890302-02-0, 2-amino-6-(Trifluoromethyl)nicotinic acid.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BABU, Suresh; BELEMA, Makonen; BENDER, John A; IWUAGWU, Christiana; KADOW, John F.; KUMARAVEL, Selvakumar; NAGALAKSHMI, Pulicharla; NAIDU, B. Narasimhulu; PATEL, Manoj; PEESE, Kevin M; RAJAMANI, Ramkumar; SAULNIER, Mark; WANG, Alan Xiangdong; (536 pag.)WO2018/203235; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 102368-13-8 , The common heterocyclic compound, 102368-13-8, name is 1,1′-Thiocarbonylbis(pyridin-2(1H)-one), molecular formula is C11H8N2O2S, 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.

1,1”-Thiocarbonyldi-2(1H)-pyridone (0.802 g, 3.45 mmol) was added to a DCM (15.70 mL) solution containing (1r,2R,6S)-2,6-dimethoxycyclohexanamine (0.5 g, 3.14 mmol). The resulting mixture was stirred overnight at RT. The reaction was concentrated and purified on silica eluting with a hexanes/EtOAc gradient (0-100%). Desired fractions were then pooled and concentrated to yield the title compound (0.45g, 71%).

The synthetic route of 102368-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 7169-97-3 ,Some common heterocyclic compound, 7169-97-3, molecular formula is C7H7BrN2O, 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.

General procedure: General procedure 13: A mixture of the corresponding aryl halide or heteroaryl halide (1.0 equiv.), CuCI (0.10 equiv.), KOH (2.0 equiv.), and ethylenediamine or propane-1 ,3-diamine (4.5 equiv.) was stirred at 20 C (for aryl iodides) or 90 C (for aryl bromides) for 12 – 24 h in a sealed vial. The mixture was allowed to cool and was then extracted with hot EtOAc (*5). The combined organics were concentrated and the excess of diamine was removed by co-evaporation with toluene. The crude material was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7169-97-3, its application will become more common.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89856-44-0 ,Some common heterocyclic compound, 89856-44-0, molecular formula is C7H9BrN2, 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.

General procedure: A mixture of aromatic aldehyde (1mmol), amidine (1mmol) and isocyanide (1mmol) was taken in 2 mL acetonitrile. Then, the catalyst bromodimethylsulfonium bromide (0.022 g, 0.1mmol) was added into it and the reaction mixture was kept for stirring at room temperature till the completion of the reaction as indicated by TLC. The solid product came out slowly which was filtered through a Buchner funnel and the solid precipitate was washed with acetonitrile. Finally it was dried under reduced pressure.

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. 89856-44-0, 5-Bromo-4,6-dimethylpyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Khan, Abu T.; Sidick Basha; Lal, Mohan; Tetrahedron Letters; vol. 53; 17; (2012); p. 2211 – 2217;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem