Pyridine-derivatives

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.93-60-7, name is Methyl nicotinate, molecular formula is C7H7NO2, molecular weight is 137.136, as common compound, the synthetic route is as follows.Application In Synthesis of Methyl nicotinate

A 10 l Buechi stirred autoclave with gas inlet tube, stirrer, internal thermometer and pressure equalizer was initially charged with 1.72 kg of methyl nicotinate (12.5 mol). 3.68 kg of diethylamine (50 mol) and 100 g of potassium tert-butoxide as a catalyst were slowly added thereto, and the mixture was homogenized while stirring.The reaction mixture thus obtained was pumped through the reaction tube continuously at 4 l/h at a working pressure of 30 bar and exposed to a microwave power of 2.8 kW, 91% of which was absorbed by the reaction mixture. The residence time of the reaction mixture in the irradiation zone was approx. 42 seconds. At the end of the reaction tube, the reaction mixture had a temperature of 285 C. Immediately after leaving the reactor, the reaction mixture was cooled to room temperature with a jacketed coil heat exchanger.A conversion of 85% of theory was attained. The reaction product was pale yellowish in color; the iron content was <5 ppm. After distillative removal of the methanol formed and of the excess or unconverted reactants, 1.85 kg of N,N-diethylnicotinamide with a purity of 98% were obtained by means of vacuum distillation. At the same time, in my other blogs, there are other synthetic methods of this type of compound,93-60-7, Methyl nicotinate, and friends who are interested can also refer to it. Reference:
Patent; CLARIANT FINANCE (BVI) LIMITED; US2012/95238; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 929000-66-8, 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.929000-66-8, name is 3-Bromo-6-chloropyridine-2-carboxylic acid, molecular formula is C6H3BrClNO2, molecular weight is 236.4505, as common compound, the synthetic route is as follows.

A mixture of 3-bromo-6-chloropyridine-2-carboxylic acid (10.0 g, 42.2 mmol, CAS 929000-66-8) in MeOH (100.0 mL)/SOCl2 (10.0 mL) was stirred at 80 C for 3 hours. The reaction mixture was concentrated in vacuo to give methyl 3-bromo-6-chloropyridine-2- carboxylate (10.4 g, 99% yield) as a yellow solid.

Statistics shows that 929000-66-8 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-6-chloropyridine-2-carboxylic acid.

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

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.60832-72-6, name is Oxazolo[4,5-b]pyridin-2(3H)-one, molecular formula is C6H4N2O2, molecular weight is 136.1082, as common compound, the synthetic route is as follows.COA of Formula: C6H4N2O2

Preparation 7 6-BROMO-3H-OXAZOLO[4,5-b]-PYRIDIN-2-ONE 0.01 mol of oxazolo[4,5-b]pyridin-2-one is dissolved in 100 ml of dimethylformamide. 0.011 mol of bromine is added via a dropping funnel. Stirring is maintained for 1 hour 30 minutes at room temperature and an ice/water mixture is added. The product is filtered off. It is washed with water. The product is dried. Yield: 90%. Melting point: 234 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60832-72-6, Oxazolo[4,5-b]pyridin-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Science et Organisation; US5084456; (1992); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 171178-46-4 , The common heterocyclic compound, 171178-46-4, name is 5-((tert-Butoxycarbonyl)amino)-2-chloroisonicotinic acid, molecular formula is C11H13ClN2O4, 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.

5-((fe/f-butoxycarbonyl)amino)-2-chloroisonicotinic acid (Intermediate B) (4.27 g, 15 mmol, 1 equiv.) was added to a 500 mL two necked oven-dried round bottom flask equipped with a stirring bar and suspended in dichloromethane (187 mL, 0.08M) was added. 4-Dimethylamino pyridine (7.40 g, 60 mmol, 4 equiv.) was added at 22C resulting in an homogeneous solution. /V-(3-dimethylaminopropyl)-/V-ethylcarbodiimide (4.65 g, 30 mmol, 2 equiv.) was added at that temperature and the crude mixture was stirred for 3 h. Anhydrous MeOH (HPLC quality), (5.5 mL, 135 mmol, 9 equiv.) was added to the solution and the mixture was stirred for 1 h at 22C. The resulting mixture was heated to reflux using an aluminium heating block for 72 h. TLC (EtOAc:MeOH 90:10 %v/v) showed complete conversion of Intermediate B into Intermediate C. The reaction was permitted to reach to 22C and volatiles were removed under reduced pressure. Dichloromethane (150 mL) was added to the residue until complete solution was achieved and the mixture was transferred to a separating funnel, washed with H2O (1 x 70 mL), HCI 1 M (2 x 50 mL) and saturated NaCI solution (1 x 50 mL). The organic phase was dried with Na2S04 and filtered through a pad of Na2S04 on a filter plate. The solvent was removed under reduced pressure giving a brown solid, which was purified by automated flash chromatography (Heptane:EtOAc, product elution with EtOAc 100%v/v) giving methyl 5-((fe/f-butoxycarbonyl)amino)-2-chloroisonicotinate as a pale yellow solid (4.04 g, 79% yield). Purity: 99.4% (UPLC-A); mp: 90.0-95.8 C; 1H- NMR (CDCI3), 5(ppm): 9.68 (bs, NH), 9.49 (s, 1 H), 7.73(s, 1 H), 7.20 (s, 1 H), 3.91 (s, 3H), 1.47 (s, 9H); LR-MS (ESI+): m/z= 287.1 Da [M+H]+, calcd. for CI2HI5CIN204: 286.2

The synthetic route of 171178-46-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FAES FARMA, S.A.; HERNANDEZ HERRERO, Gonzalo; GARCIA DOMINGUEZ, Neftali; ZAZPE ARCE, Arturo; OLIVERA TIZNE, Roberto; NOVERGES PEDRO, Barbara; CORCOSTEGUI VIVAR, Reyes; TATO CERDEIRAS, Paloma; (124 pag.)WO2020/20939; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 144100-07-2, 2-Bromo-6-fluoropyridine, 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, Quality Control of 2-Bromo-6-fluoropyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Bromo-6-fluoropyridine

A solution of 2-bromo-6-fluoropyridine (2.4 g, 13.64 mmol), o-tolylboronic acid (2.039 g, 15.00 mmol) and Tetrakis (0.158 g, 0.136 mmol) in Dioxane was degassed by nitrogen bubble for 10 min. A solution of Phosphoric acid, potassium salt (8.68 g, 40.9 mmol) in H20 (2ml) was then added and the solution heated to reflux for 18 h. The crude material was purified via silica gel chromatography (90g SiOi column, hexane:EtOAc 100:0 -> 90: 10) to afford 2-fluoro-6-(o-tolyl)pyridine, 2.41 g (94percent). NuMuRhonu (400 MHz, CDCb) delta 7.87 (q, J=8.2 Hz, 1H), 7.46 – 7.41 (m, 1H), 7.37 – 7.26 (m, 4H), 6.92 (dd, J=8.2, 2.9 Hz, 1H), 2.43 (s, 3H).

The synthetic route of 144100-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BOWSHER, Michael S.; DESKUS, Jeffrey; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (220 pag.)WO2018/127801; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16063-69-7, Adding some certain compound to certain chemical reactions, such as: 16063-69-7, name is 2,4,6-Trichloropyridine,molecular formula is C5H2Cl3N, 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 16063-69-7.

To a mixture of 2,4,6-trichloropyridine (5 g, 27.5 mmol. 1 eq), morpholine (7.2 mL, 82.3mmol, 3 eq), sodium tert-butoxide (7.9 g, 82.3 mmol, 3 eq), (2-biphenyl)di-tert-butyl-phosphine (408 mg, 2.7 mmol, 0.05 eq) in tetrahydrofuran (80 mL) was added Pd(dppf)C12 (from Combi-blocks, product number: OT-0746), 1 g, 2.7 mmol, 0.05 eq). The mixture was stirred at 8000 for 4 h. The mixture was cooled down to room temperature and poured onto a saturated solution of NH4CI (100 mL). The phases were separated and theaqueous phase was extracted with ethyl acetate (2 x 100 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure using a rotary evaporator. Products Bi and B2 were isolated by flash chromatography on silica gel using first a 1:4.5 mixture of ethyl acetate and cyclohexane and then 1:1 mixture of ethyl acetate and cyclohexane as eluent. The product fractionswere pooled and evaporated to yield Bi as an off white powder (2.45 g, 8.6 mmol, 31%)and B2 as an off white powder (2.2 g, 7.8 mmol, 28% yield).

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. 16063-69-7, 2,4,6-Trichloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITAET BASEL; PIQUR THERAPEUTICS AG; HEBEISEN, Paul; BEAUFILS, Florent; LANGLOIS, Jean-Baptiste; WO2015/162084; (2015); 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.1970-81-6, name is [3,3′-Bipyridine]-5-carboxylic acid, molecular formula is C11H8N2O2, molecular weight is 200.19, as common compound, the synthetic route is as follows.Recommanded Product: 1970-81-6

Referring to Scheme 1, synthesis of compound 13, to a cooled (0C) suspension of compound 2 (0.6 g, 3.0 mmol) in dichloromethane (100 mL), was added N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.69 g, 3.6 mmol), 1-hydroxy-benzotriazole hydrate (0.49 g, 3.6 mmol), and triethylamine (0.5 mL, 3.6 mmol). After stirring for 30 min. at 0C (the reaction became almost clear), compound 9 (0.4 g, 1.2 mmol) and triethylamine (1.0 mL, 7.2 mmol) were added. The reaction was stirred for 16 h., then washed with saturated NaHCO3 (3 x 50 mL). The DCM layer was dried with MgSO4, reduced in volume in vacuo, and purified by flash column chromatography (2% – 25% methanol in DCM) to give compound 13 (90 mg, 12%). 1H NMR (CDCl3, 500 MHz) delta 1.70 (m, 2H), 1.75 (m, 2H), 1.87 (m, 2H), 1.89 (s, 3H), 1.98 (m, 1H), 2.14 (m, 1H), 3.28 (m, 1H), 3.35 (m, 1H), 3.40 (m, 2H), 3.64 (m, 1H), 3.70 (m, 1H), 4.85 (q, J = 4.9 Hz, 1H), 5.30 (s, 1H), 5.67 (s, 1H), 6.40 (t, J = 5.0 Hz, 1H), 7.36 (t, J = 5.0 Hz, 1H), 7.42 (dd, J = 3.9, 2.2 Hz, 1H), 7.43 (dd, J = 3.9, 2.2 Hz, 1H), 7.65 (t, J = 4.45 Hz, 1H), 7.72 (d, J = 6.1 Hz, 1H), 7.93 (d, J = 1.5 Hz, 1H), 7.95 (d, J = 1.5 Hz, 1H), 8.42 (m, 2H), 8.67 (dd, J = 4.1, 1.0 Hz, 1H), 8.68 (dd, J = 4.0, 1.2 Hz, 1H), 8.889 (s, 1H), 8.891 (s, 1H), 8.93 (d, J = 1.7 Hz, 1H), 8.96 (d, J = 1.8 Hz, 1H), 9.10 (d, J = 1.6 Hz, 1H), 9.13 (d, J = 1.7 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1970-81-6, [3,3′-Bipyridine]-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; MEDTRONIC MINIMED, INC.; GAMSEY, Soya; WESSLING, Ritchie, A.; EP2222686; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6271-78-9, 6-Chloropyridine-3-carboxamide, 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, Quality Control of 6-Chloropyridine-3-carboxamide, blongs to pyridine-derivatives compound. Quality Control of 6-Chloropyridine-3-carboxamide

A solution of 6-chloronicotinamide (15 g, 95.8 mmol) and hexamethyleneimine(11.4 g, 115 mmol) in DMSO (20 mL) was heated at 60 oC for 12 hours afterwhich TLC indicate complete consumption of the starting material. The mixturewas diluted with water which resulted in the formation of a thick precipitate andrequired further dilution to give a free-flowing mixture to filter (300 mL water).The solid was filtered off and washed with water (50 mL). The solid wasdissolved in DCM (500 mL) and EtOAc (500 mL), dried (Na2SO4), filtered, andconcentrated in vacuo. The resulting solid was suspended in EtOAc and filteredto give 13 as a beige crystalline solid (12 g, 57%).1H NMR (400 MHz, DMSO-d6): delta 1.4 – 1.5 (m, 4H), 1.6 – 1.7 (m, 4H), 3.5 – 3.7(m, 4H), 6.6 (d, J = 9.2 Hz, 1H), 7.0 (br s, 1H), 7.6 (br s, 1H), 7.9 (dd, J = 2.4 Hz,J = 9.2 Hz, 1H), 8.5 (d, J = 2.4 Hz, 1H). 13C NMR (100 MHz, DMSO-d6): delta 26.8,27.4, 47.6, 104.5, 117.2, 137.0, 149.0, 159.3, 167.5. MS (ESI) m/z: [M – H]+Calculated for C12H16N3O: 218.27; Found: 218.4. Purity: >99.0%.

The synthetic route of 6271-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jalily, Pouria H.; Eldstrom, Jodene; Miller, Scott C.; Kwan, Daniel C.; Tai, Sheldon S.-H.; Chou, Doug; Niikura, Masahiro; Tietjen, Ian; Fedida, David; Molecular Pharmacology; vol. 90; 2; (2016); p. 80 – 95;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 24484-93-3, name is Methyl 4-chloropicolinate. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H6ClNO2

Under nitrogen, tetrahydronfuran (10.86 kg) was added into a reactor (30 L). After the mixer was started, (N-(methyl-d3))amine hydrochloride (1.50 kg, 21.26 mol, 1.5 eq), methyl 4-chloropicolinate (2.43 kg, 14.16 mol, 1 eq) and anhydrous potassium carbonate (3.92 kg, 28.36 mol, 2 eq) were added in turn. The reaction was conducted at 33 C. for 15 h, and then pure water (12.20 kg) was added. The reaction mixture was extracted with methyl tert-butyl ether (3.70 kg×2). The organic phases were combined, dried over anhydrous sodium sulfate (0.50 kg) and stirred for 1 hour, and filtered. The solvents were removed under vacuum (?0.09 MPa) at 40±2C. with water bath to give the title compound («2.41 kg», purity 99.0%, yield «98%») as a light «yellow» oil.1H NMR(DMSO-d6, 400 MHz): delta7.64 (dd, J=2 Hz, 5.2 Hz, 1H), 7.97 (d, J=1.6 Hz, 1H), 8.54 (d, J=5.2 Hz, 1H), 8.74 (br, 1H). MS (ESL m/z) calcd. for C7H4D3ClN2O: 173, found:» 174 [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 24484-93-3.

Reference:
Patent; SUZHOU ZELGEN BIOPHARMACEUTICAL CO., LTD.; Feng, Weidong; Gao, Xiaoyong; Dai, Xiaojun; US2013/35492; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 144750-42-5, 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. 144750-42-5, name is (S)-2-(2-Chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetic acid hydrochloride, molecular formula is C15H15Cl2NO2S, 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 10: Preparation of methyl (S)-(+)-alpha -(2-chlorophenylV6,7- dihydrothieno[3,2-a]pyridine-5(4H)-acetate (formula (I): 41.8 g of (S)-(+)-alpha -(2-chlorophenyl)-6,7-dihydro-4Eta-thieno[3,2- c]pyridine-5(4H)-acetic acid hydrochloride obtained in Example 6 was suspended in 252 ml of dichloromethane, 0.94 ml of dimethylformamide was added thereto and cooled to -20 C . A mixture of 12.8 ml of oxalyl chloride and 84 ml of dichloromethane was slowly added thereto at below – 10 C over a period of 30 min, and then stirred at a temperature in the range of -10 to 0C for 2 hrs. A mixture of 24.6 ml of methanol and 84 ml of dichloromethane was added thereto over a period of 30 min, the resulting mixture was heated to room temperature and then stirred at the same temperature for 2 hrs. 170 ml of water was slowly added to the resulting solution, the pH was adjusted to 7.5 using saturated sodium bicarbonate to induce phase separation. The resulting organic layer was separated, washed with 150 ml of saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure, to obtain 37.1 g of the title compound as a yellow oil (yield: 95%), which was identical to that obtained in Example 7. optical purity : 98.5 % ee (HPLC)

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 144750-42-5, (S)-2-(2-Chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetic acid hydrochloride.

Reference:
Patent; HANMI PHARM. CO., LTD.; WO2006/137628; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem