Tag: M.W:100-200

Application of 80194-69-0, 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 80194-69-0, name is 5-(Trifluoromethyl)picolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of (1S, 4S)-2-{(15)-1-[4-(allyloxy)-2,3-dimethylphenyl]ethyl}-2,5-diazabicyclo-[2.2.1]heptane (7.3 g, 25.5 mmol), 5-(trifluoromethyl)pyridine-2-carboxylic acid (4.97 g, 26.0 mmol), BOP (16.9 g, 38.3 mmol) and NEt3 (8.89 mL, 63.8 mmol) in N,N-dimethylacetamide (50 mL) is heated at 40 C. under N2 overnight. The reaction mixture is cooled to room temperature, diluted with 1N NaOH (100 mL), and extracted with EtOAc. The organic layer is isolated, washed with 1N NaOH, water and brine, dried over Na2SO4, and concentrated under reduced pressure. The residue is purified by silica gel chromatography with EtOAc as the eluent to afford the title compound as a brown oil. 1HNMR (400 MHz, CDCl3) delta: 8.86 (s, 0.67H), 8.83 (s, 0.33H), 8.02-8.13 (m, 2H), 7.28 (m, 1H), 6.72 (m, 1H), 6.07 (m, 1H), 5.43 (m, 1H), 5.26 (m, 1H), 4.97 (s, 1H), 4.49-4.53 (m, 2H), 3.72-4.00 (m, 2H), 3.52 (m, 1H), 3.35 (m, 1H), 3.22 (m, 1H), 2.83 (d, 0.67H), 2.78 (d, 0.33H), 2.33 (s, 2H), 2.25 (s, 1H), 2.21 (s, 2H), 2.19 (s, 1H), 1.95 (m, 1H), 1.72 (m, 1H), 1.25-1.31 (m, 31). LC-MS m/z (M+H): 460.

According to the analysis of related databases, 80194-69-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hutchinson, Alan J.; Chenard, Bertrand L.; Li, Guiying; Ghosh, Manuka; Tarrant, James G.; Yoon, Taeyoung; Luke, George P.; Lee, Kyungae; O’Donnell, Mary-Margaret E.; Pringle, Wallace C.; Peterson, John M.; Hodgetts, Kevin J.; Steenstra, Cheryl K.; Doller, Dario; US2006/9456; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 63071-10-3, 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. 63071-10-3, name is (4-Chloropyridin-2-yl)methanol, molecular formula is C6H6ClNO, 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 61 1-(4-(4-(2-(hydroxymethyl)pyridin-4-yl)benzyl)phenyl)-5-methyl-1H-pyrazole-3-carboxamide A microwave vial was charged with Intermediate III (60 mg, 0.144 mmol), (4-chloro-2-pyridinyl)methanol (24.77 mg, 0.173 mmol), K3PO4 (92 mg, 0.431 mmol), second generation Xphos Precatalyst (11.31 mg, 0.014 mmol), water (0.5 mL), THF (2 mL), and was evacuated and degassed with N2 for 5 min. The mixture was heated in the microwave at 100 C. for 2 hr, cooled to RT, and concentrated in vacuo. The resulting crude product was purified by FCC (gradient 2%-10% MeOH in DCM) then by preparative HPLC to afford 1-(4-(4-(2-(hydroxymethyl)pyridin-4-yl)benzyl)phenyl)-5-methyl-1H-pyrazole-3-carboxamide (2 mg, 3%): LCMS Rt=1.23 min (condition A), MS (M+1)=399.4. 1H NMR (400 MHz, Methanol-d4) delta 8.48 (dd, J=5.3, 0.8 Hz, 1H), 7.82 (dd, J=1.8, 0.9 Hz, 1H), 7.78-7.66 (m, 2H), 7.57 (dd, J=5.3, 1.9 Hz, 1H), 7.51-7.30 (m, 6H), 6.68 (d, J=0.9 Hz, 1H), 4.75 (s, 2H), 4.14 (s, 2H), 2.33 (d, J=0.7 Hz, 3H).

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 63071-10-3, (4-Chloropyridin-2-yl)methanol.

Reference:
Patent; NOVARTIS AG; DALES, Natalie; GORMISKY, Paul; KERRIGAN, John Ryan; SHU, Lei; (159 pag.)US2019/77773; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 10386-27-3, 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. 10386-27-3, name is 2-Bromoisonicotinonitrile, molecular formula is C6H3BrN2, 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.

StepD: (4S)-tert-Butyl 4-((l-(2-chlorophenyl)-2-(3,3-difluorocyclobutylamino) -2-oxoethyl){3- fluorophenyl)carbamoyl)-3-(4-cyanopyridin-2-yl)-2-oxoimidazolidine-l-carboxylate. To a 25 mL flask charged with 1,4-dioxane (4.5 mL) were added(4S)-tert-butyl4-((l-(2-chlorophenyI)- 2-(33-difluoro cyclo butylamino)-2-oxoethyl)(3-fiuoro -phenyl)carbamoyl)-2-oxoimidazolidine- 1- carboxylate (250 mg, 0.43 mmol), 2-bromoisonicotinonitrile (122 mg 0.65 mmol), CS2CO3 (281 mg, 0.862 mmol), Xant-Phos (25 mg 0.043 mmol) and Pd2(dba)3 (40 mg, 0.043 mmol). The mixture was degassed and refilled with nitrogen, and then heated to 100 °C for 3 hr. The resulting mixture was cooled and filtered. The filtrate was concentrated in vacuo and the residue was purified by a standard method to give both epimers. The epimers were further separated by a standard method to give the desired product. ‘HNMR (400 MHz, CDC13): delta 8.58 (s, 1H), 8.48 (t, J= 5.9 Hz, 1H), 7.71 (d, J= 8.4 Hz, 1H),7.37 – 7.16 (m, 4H), 7.15 – 6.76 (m, 4H), 6.56 – 6.31 (m, 2H), 4.95 – 4.75 (m, 1H), 4.31 (s, 1H), 3.86 (dd,J= 10.8, 5.1 Hz, 1H), 3.66 (m, 1H), 2.99 (m, 2H),2.61 -2.27 (m, 2H), 1.56 (s,9H).MS : 683(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 10386-27-3, 2-Bromoisonicotinonitrile.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10297; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 791644-48-9 ,Some common heterocyclic compound, 791644-48-9, molecular formula is C6H2ClFN2, 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 compound 4 (50 g, 321.7 mmol) in 1- butanol (1 L) was added hydrazine monohydrate (150 mL, 3.2 mol) , and the mixture was refluxed for 4 h. The mixture was cooled to room temperature and concentrated. The precipitate was successively washed on filter with water (2x) and Et2<0 (2x) and dried in vacuo overnight to give compound 5 (44 g, 88%) as a yellow solid. 1H NMR (DMSO-d6, 300 MHz): delta 5.53 (s, 2H); 7.94 (dd, IH); 8.35 (dd, IH); 12.02 (s, IH). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,791644-48-9, its application will become more common. Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/18415; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65753-47-1, Adding some certain compound to certain chemical reactions, such as: 65753-47-1, name is 2-Chloro-3-(trifluoromethyl)pyridine,molecular formula is C6H3ClF3N, 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 65753-47-1.

2-Chloro-3-trifluoromethyl-pyridine (3 g, 16.53 mmol) was dissolved in 30ml of a solution of sodium methoxide (5.4M) in methanol. The mixture was stirred at ambient temperature for 2 days. After this period of time, the reaction was taken into ice and extracted with DCM three times. The combined extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give 2-methoxy-3-trifluoromethyl-pyridine as a light liquid (2.7 g, 89% yield). 1 H-NMR (400 MHz, DMSO-d6, 298 K): ? ppm 3.98 (s, 3H) 7.2 (dd, 1 H) 8.1 1 (d, 1 1-1) 8.45 (d, 1 H). MS: 178.1 [M+1 ]+, Rt(1) =1 .29 min.

According to the analysis of related databases, 65753-47-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; LEWIS, Ian; SMITH, Alexander, Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; WOLF, Romain; ZECRI, Frederic; WO2013/57711; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 97483-77-7 ,Some common heterocyclic compound, 97483-77-7, molecular formula is C6H3BrN2, 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.

Pyridine (40.0 mL, 4.0 v/w) was placed in a reactor, and zinc chloride (11.2 g, 81.9 mmol) was added dropwise at 40C or less. Thereafter, sodium azide (8.90 g, 137 mmol) and 5-bromo-2-cyanopyridine (10.0 g, 54.6 mmol) were added into the reactor, and the reaction mixture was stirred to reflux at 120C for 2 hr. After the termination of the reaction, the reaction product was cooled to room temperature, added with purified water (200 mL, 20.0 v/w), stirred at room temperature for 1 hr, filtered, and washed with purified water (200 mL, 20.0 v/w). The filtered solid was added with a 6 N hydrochloric acid aqueous solution (200 mL, 20.0 v/w) and then stirred at room tem[43jperature for 2 hr. The reaction product was filtered, washed with purified water (200mL, 20.0 v/w), and concentrated under reduced pressure, thus yielding a desired whitecompound. Yield (11.34 g, 91.8%), Purity 99.4%5-bromo-2-(2H-tetrazol-5-yl)pyridine:1H NMRoe (DMSO-d6, ppm) 8.95 (d,1H), 8.35 (dd,1H), 8.17 (d,1H)

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. 97483-77-7, 5-Bromopicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ST PHARM CO., LTD.; WOO, Seok Hun; CHOI, YunHee; KIM, Hong Jun; CHANG, Sun Ki; LIM, Geun Jho; (14 pag.)WO2017/99530; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1796-83-4, 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 1796-83-4, name is Dimethyl pyridine-3,4-dicarboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Step A. Dimethyl pyridine-3,4-dicarboxylate 1 -oxideTo a stirred mixture of dimethyl pyridine-3,4-dicarboxylate (10.13 g, 51.9 mmol) and urea hydrogen peroxide (9.80 g, 104 mmol) in CH3CN (100 mL) at 0 0C was added dropwise trifluoroacetic anhydride (22.31 g, 106 mmol). The reaction mixture was stirred at 0 10 0C for 2 h, and then saturated aqueous sodium bisulfite (80 mL) was added slowly and the quenched mixture was diluted with 0.5 N HCl (300 mL) and extracted with CH2Cl2 (3 x 400 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: mlz = 212 (M + 1).

According to the analysis of related databases, 1796-83-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2009/120652; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 54664-55-0, 4-Chloro-6,7-dihydro-5H-cyclopenta[b]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, HPLC of Formula: C8H8ClN, blongs to pyridine-derivatives compound. HPLC of Formula: C8H8ClN

Step 3 : 4-chloro-6,7-dihydro-5H-cvclopentarb1pyridine-l-oxide To a solution of 4-chloro-6,7- dihydro-5H-cyclopenta[b]pyridine (38 g, 247 mmol) and methyl trioxorhenium(VII) (400 mg, 1.61 mmol) in DCM (250 mL) was added hydrogen peroxide (76 mL, 742 mmol, 30%wt). After addition, the mixture was stirred at 20C for 48h. TLC showed SM was consumed. The mixture was diluted with DCM (300 mL) and water (150 mL), quenched with solid powder sodium sulfite portionwise until potassium iodide-starch test paper (the paper wetted by lmol/L aqueous HC1) did not turn blue. The organic phase was separated and the aqueous phase was extracted with CHCI3 (500 mL chi 3). The combined organic phases were dried over Na2S04, filtered and concentrated to give the title compound, which was used for the next step without further purification.

The synthetic route of 54664-55-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERTZ, Eric; EDMONDSON, Scott, D.; SO, Sung-Sau; SUN, Wanying; LIU, Weiguo; NEELAMKAVIL, Santhosh, F.; GAO, Ying-Duo; HRUZA, Alan; ZANG, Yi; ALI, Amjad; MAL, Rudrajit; HE, Jiafang; KUANG, Rongze; WU, Heping; OGAWA, Anthony, K.; NOLTING, Andrew, F.; (152 pag.)WO2016/168098; (2016); 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. 82257-09-8, name is 3-Bromo-4-methoxypyridine, the common compound, a new synthetic route is introduced below. SDS of cas: 82257-09-8

To a stirred solution of tert-butyl 4-[(2-{[6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 Hbenzimidazol-2-yl]amino}pyridin-4-yl)methyl]piperazine-1 -carboxylate (400 mg, 748 pmol) and 3-bromo-4-methoxypyridine (169 mg, 898 pmol) in dioxane (4 mL) and water (0.7 mL) wasadded sodium carbonate (238 mg, 2.25 mmol) and Pd(dppf)Cl2. CH2CI2 (91.7 mg, 112 pmol). The mixture was heated to reflux for 24 h. Further 3-bromo-4-methoxypyridine (70 mg) was added and the mixture was heated to reflux for 24 h. Dichioromethane was added, the mixture was dried (magnesium sulfate), filtered and the solvent was removed in vacuum. Silicagel chromatography gave 16.0 mg (4% yield) of the title compound as a crude product that wasused without further purification.LC-MS (Method 2): R = 1.20 mm; MS (ESIpos): m/z = 516 [M+H]1H-NMR (400 MHz, CHLOROFORM-d) oe [ppm]: 1.261 (0.74), 1.468 (16.00), 2.330 (1.89),3.394 (1.99), 3.444 (1.92), 3.927 (1.16), 6.927 (0.58), 6.941 (0.64), 6.953 (0.79), 6.965 (0.70),7.081 (1.09), 8.283 (0.78), 8.296 (0.74), 8.483 (0.57), 8.497 (0.56), 8.540 (1.04).

The synthetic route of 82257-09-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 913090-41-2, 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.913090-41-2, name is 6-(Difluoromethyl)pyridin-3-amine, molecular formula is C6H6F2N2, molecular weight is 144.1221, as common compound, the synthetic route is as follows.

A solution of the compound obtained in Step D (2.1 g) and JV-bromo- succinimide (2.56 g) in acetonitrile (50 ml) was stirred at 00C for 10 minutes. The reaction mixture was poured into water and extracted several times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and then concentrated in vacuo. Chromatography on silica gel (eluent: hexane / ethyl acetate 1 : 1) afforded 2-bromo-6- difluoromethyl-pyridin-3-yl-amine (2.5 g) as a solid. MS (ES+) 223 / 225 (MH+); IH NMR (400 MHz, CDCl3) 4.38 (br s, 2H), 6.52 (t, IH), 7.08 (d, IH), 7.41 (d, IH).

The chemical industry reduces the impact on the environment during synthesis 913090-41-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; PITTERNA, Thomas; CASSAYRE, Jerome Yves; CORSI, Camilla; MAIENFISCH, Peter; WO2010/9968; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem