Category: pyridine-derivatives

Electric Literature of 16179-97-8, Adding some certain compound to certain chemical reactions, such as: 16179-97-8, name is 2-(Pyridin-2-yl)acetic acid hydrochloride,molecular formula is C7H8ClNO2, 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 16179-97-8.

Pyridine (60 mL, 730 mmol) was added to a mixture of 5-(((1 R,3SJ-3-(5-amino- 1 ,3,4-thiadiazol-2-yl)cyclopentyl)methyl)-1 ,3,4-thiadiazol-2-amine (12.25 g, 43.4 mmol) and 2-pyridylacetic acid hydrochloride (18.8 g, 108 mmol). After stirring for 5 min, T3P (72.3 mL, 50% in DMF, 121 mmol) was added. Upon addition, a minor exotherm was observed, accompanied by effervesence. The reaction was stirred for 15 min and then checked by LCMS. The mono-acylated product was still observed, and as such additional 2-pyridylacetic acid hydrochloride (5 g, 28.7 mmol), T3P (10 mL, 50% in DMF, 16.7 mmol) and pyridine (20 mL, 243 mmol) were added and the reaction stirred overnight. The reaction was concentrated to remove excess pyridine, and then the residue was added dropwise to water with stirring. After addition was complete, the mixture was brought to pH ~7.5 and the solids filtered off, and rinsed with water. The solids were triturated with acetone and filtered to give 2-(pyridin-2-yl)-/V-(5-{[(1 R,3S)-3- {5-[(pyridin-2-ylacetyl)amino]-1 ,3,4-thiadiazol-2-yl}cyclopentyl]methyl}-1 ,3,4-thiadiazol-2- yl)acetamide (14.6 g, 65 %) as a yellow solid. 1 H NMR (400 MHz, DMSO-cf6) delta ppm 12.65 (br s, 2 H), 8.49 (d, J = 4.77 Hz, 2 H), 7.77 (td, J = 7.6, 1 .9 Hz, 2 H), 7.39 (d, J = 7.8 Hz, 2 H), 7.28 (ddd, J = 7.6, 4.9, 1.2 Hz, 2 H), 4.00 (s, 4 H), 3.50 (dt, J = 10.3, 7.7 Hz, 1 H), 3.07 (d, J = 7.3 Hz, 2 H), 2.35 – 2.47 (m, 1 H), 2.29 (dt, J = 13.5, 7.1 Hz, 1 H), 2.12 (dtd, J = 15.9, 8.9, 7.7, 3.8 Hz, 1 H), 1 .76 – 1 .96 (m, 2 H), 1 .44 – 1 .61 (m, 2 H). m/z (ESI+) for C24H24N802S2 521 .1 (M+H)+.

According to the analysis of related databases, 16179-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; BURNS, Aaron Craig; COLLINS, Michael Raymond; GREASLEY, Samantha Elizabeth; HOFFMAN, Robert Louis; HUANG, Qinhua; KANIA, Robert Steven; KUNG, Pei-Pei; LINTON, Maria Angelica; NARASIMHAN, Lakshmi Sourirajan; RICHARDSON, Paul Francis; RICHTER, Daniel Tyler; SMITH, Graham; WO2015/166373; (2015); 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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Recommanded Product: 5-Methylpyridin-2(1H)-one

To a 25 mL round bottom flask was added 0.10 g (1 mmol, 1 quiv.) Of compound 3, 0.17 g (1 mmol, 1 quiv.) Of p-bromobenzaldehyde, 1.4 g (10 mmol, 10 equiv.) Of K2CO3,0.05 g (0.26 mmol, 0.26 equiv.) CuI,5 mL of DMF as solvent,Reflux stirring reaction 1h,TLC, the reaction was completed, the mixture was cooled, the mixture was extracted with 30 mL of water and extracted with 3 x 20 mL of ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, spin dried and separated by 300 mesh silica gel column chromatography. Eluent petroleum ether: ethyl acetate = : 3 (v / v) to give pale yellow solid: Compound 4.

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, 1003-68-5, 5-Methylpyridin-2(1H)-one.

Reference:
Patent; Sichuan Univeristy; Yi, Shufan; Li, Yong; Cao, Tingting; Yang, Ziyao; (17 pag.)CN106083702; (2016); A;,
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. 139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid, molecular formula is C8H6N2O2, 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 Imidazo[1,2-a]pyridine-6-carboxylic acid

To a solution of imidazo[1,2-a]pyridine-6-carboxylic acid (87mg, 0.54mmol) and C-(5-(3-fluorophenoxy)thiophen-2-yl)methylamine (120mg, 0.54mmol) in N,N-dimethylformamide (5mL) were added benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (240mg, 0.54mmol) and triethylamine(0.15mL, 1.08mmol), and the solution was stirred for 40 minutes at 80C. Water and ethyl acetate were added to the reaction mixture for extraction, and the organic layer was washed twice with water. Silica gel was added to the organic layer, solvent was evaporated in vacuo for adsorption, purification was carried out by silica gel column chromatography (hexane : ethyl acetate = 1 : 1, then ethyl acetate), and the title compound (90mg, 0.25mmol, 45.4%) was obtained as a light brown oil. 1H-NMR Spectrum (DMSO-d6) delta(ppm): 4.55 (2H, d, J=5.6Hz), 6.58 (1H, d, J=4.0Hz), 6.83 (1H, d, J=4.0Hz), 6.90-7.00 (3H, m), 7.40 (1H, ddd, J=8.0, 8.0, 8.0Hz), 7.57-7.66 (3H, m), 8.04 (1 H, s), 9.12 (1 H, d, J=0.8Hz), 9.20 (1 H, t, J=5.6Hz).

With the rapid development of chemical substances, we look forward to future research findings about 139022-25-6.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 106047-17-0, 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.106047-17-0, name is Methyl 4-(pyridin-4-yl)benzoate, molecular formula is C13H11NO2, molecular weight is 213.23, as common compound, the synthetic route is as follows.

Reference Example 18 Methyl 4-[pyridine-N-oxide-4-yl]-benzoate. To a cooled (0 C.) solution of methyl 4-[pyridin-4-yl]-benzoate (2.1 g, 10 mmol) (reference example 19a) in CH2Cl2 (41 mL) is added m-CPBA (3.4 g, 50-60% technical grade, 10 mmol). The resulting solution is stirred for 1 hour then a further portion of m-CPBA added (1.7 g, 5 mmol). This solution is stirred for 1 hour (temperature held between 5-10 C.) then the reaction mixture poured directly onto a silica gel column. Elution with 10% MeOH/40% EtOAc/50% CH2Cl2 gave 2.0 g of the title compound as a tan solid. 1H NMR (CDC3OD) d 3.94 (s, 3H), 7.90 (m, 4H), 8.14 (d, J=8.5 Hz, 2H), 8.39 (d, J=7 Hz, 2H). MS (EI) m/z 230 (M)+.

Statistics shows that 106047-17-0 is playing an increasingly important role. we look forward to future research findings about Methyl 4-(pyridin-4-yl)benzoate.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US6541505; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 20260-53-1, 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. 20260-53-1, name is Nicotinoyl chloride hydrochloride. A new synthetic method of this compound is introduced below.

jOZllj To a stirred solution of 4-aminobeuzene-1,3-diol hydrochloride (0.50 g, 3.09 mmol) in pyridine (6 mL) with ice cooling, was added ilicotinoyl chloride hydrochloride (0.55 g, 3.09 mmol) portion-wise. The mixture was stirred at room temperature for 16 hours. The mixiure was concentratci1 in vucuo and the residue was diluted with water (50 mL) and extracted with ethyl aceffite (2 x 60 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Purification by FCC (silica, 30-100% ethyl acetate in heptane) gave the title compound 148 mg (21% yield) as a light brown solid. 6H NMR (250 MHz, DMSO) 9.47 (d, J= 88.0 Hz, 3H), 9.10 (d, J = 1.7 Hz, 1R), 8.73 (dd, J = 4.8, 1.5 Hz, 1H), 8.28 (dt, J = 7.9, 1.9 Hz, 1H), 7.53 (dd, J = 7.7, 5.1 Hz, 1H), 7.20 (d, J = 8.6 Hz, 1H),6.36 (d, I = 2.6 Hz, 1H), 6.24 (dd, J = 8.6, 2.6 Hz, 1H). Tr(METCRI27S) = 0.79 mm, (ESt) (MtH)t 23 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,20260-53-1, its application will become more common.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; KISELYOV, Alex; BROWN, Christopher, John; GALAN, Sebastien, Rene Gabriel; PRIME, Michael, Edward; GILES, Paul, Richard; GADOULEAU, Elise, Luciennen Paulette; KRUeLLE, Thomas, Martin; CLARK-FREW, Daniel; JOHNSON, Peter, David; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; COE, Samuel; HAYES, Sarah; (271 pag.)WO2016/33445; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17368-12-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 17368-12-6 as follows.

A solution of 2-chioropyridin-4-ol (1.0 g, 7.72 mmoi) in DMF (20 rnL) was treated wtih i,i-difluoro-2-iodoethane (1.14 mL, 1.92 mmol) and K2C03 (1.6 g, 11.58 mmol)and heated at 60 C overnight, The reaction was diluted with EtOAc and washed with saturated, aqu. NaHCO3, then with brine. The organics were dried over Na2SO4, filtered,and concentrated, The crude material was purified by chromatography on silica (0-30% EtOAc in hexanes) to give the title compound as an oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17368-12-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; SKUDLAREK, Jason; (79 pag.)WO2016/95204; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52334-90-4, 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.52334-90-4, name is 3-Methoxypyridin-4-amine, molecular formula is C6H8N2O, molecular weight is 124.1405, as common compound, the synthetic route is as follows.

Under an atmosphere of argon, 60.0 mg (0.16 mmol) of 5-{[6-(2-fluorophenyl)pyridin-3- yl]carbamoyl}-2-methoxybenzoic acid (intermediate 23) and 24.4 mg (0.20 mmol) of 3-methoxypyridin-4-amine were dissolved in 3.94 mL of anh DMF. 86 ilL (0.49 mmol) of N-ethyl-Nisopropylpropan-2-amine and 102.3 mg (0.20 mmol) of PYBOP were added and it was stirred at rt over night. The reaction mixture was concentrated on a rotavap and the residue was purified py HPLC (Waters XBrigde C18 5j1 lOOx3Omm; water + 0.2% vol. ammonia (32%) / acetonitril gradient; temperature: room temperature; injection: 250 ilL; DAD scan: 210-400 nm) affording 24.2 mgmaterial which was impure and was purified further by HPLC (method 5) giving 2 mg (2% of theory) of the title compound.?H-NMR (300 MHz, DMSO-d6) 6 [ppm]: 2.270 (2.86), 2.725 (2.86), 3.884 (1.56), 4.085 (16.00), 4.196 (15.35), 7.297 (1.82), 7.336 (5.07), 7.365 (4.03), 7.437 (1.69), 7.460 (2.86), 7.488 (4.68), 7.518 (3.90),7.820 (2.73), 7.848 (2.86), 7.943 (1.69), 7.970 (2.73), 7.996 (1.56), 8.216 (2.60), 8.236 (3.12), 8.273 (2.60), 8.310 (3.77), 8.346 (2.60), 8.392 (4.68), 8.407 (7.15), 8.783 (4.42), 9.093 (4.29), 10.709 (4.29), 10.758 (4.68).LC-MS (Method 3): R = 1.19 mm; MS (ESIpos): m/z = 473 [M+H].

Statistics shows that 52334-90-4 is playing an increasingly important role. we look forward to future research findings about 3-Methoxypyridin-4-amine.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; BENDER, Eckhard; SCOTT, William; RICHTER, Anja; ZORN, Ludwig; LIU, Ningshu; MOeNNING, Ursula; SIEGEL, Franziska; GOLZ, Stefan; HAeGEBARTH, Andrea; LIENAU, Philip; PUEHLER, Florian; BASTING, Daniel; SCHNEIDER, Dirk; MOeWES, Manfred; (130 pag.)WO2016/131794; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52833-94-0, 2-Amino-5-bromonicotinic acid, 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, name: 2-Amino-5-bromonicotinic acid, blongs to pyridine-derivatives compound. name: 2-Amino-5-bromonicotinic acid

Step 2: 5-Bromo-3-(3-(2,2,2-trifluoroethyl)-1 ,2,4-oxadiazol-5-vl)pyridin-2-amine To a stirring suspension of 2-amino-5-bromonicotinic acid (2.3 g, 10.60 mmol) in DCM (53.0 ml), 1-chloro-N,N,2-trimethyl-1-propenylamine (Ghosez’s reagent) (1.683 ml, 12.72 mmol) was added. The reaction mixture was left stirring for 1.5 hours. 3,3,3-trifluoro-N’- hydroxypropanimidamide (step 1) (1.656 g, 11.66 mmol) was then added followed by DIPEA (3.70 ml, 21.20 mmol). The reaction mixture was stirred overnight. T3P (18.56 ml, 31.8 mmol) was added to the mixture and this was microwaved for 3 hours at 100C. The mixture was added to water (100ml) and product extracted into EtOAc (2 x 90ml). The organic extracts were washed with brine, dried over MgS04 and the filtrate was concentrated under reduced pressure. The crude product was purified by adding MeOH (~10ml). The mixture was sonicated and the resulting solid collected by filtration, washed with MeOH and dried to afford the title compound; LCMS: Rt = 1.17 mins; MS m/z 325.0 [M+H]+; Method 2minLowpHv01 1H NMR (400 MHz, DMSO-d6) delta 8.40 (1 H, d), 8.35 (1 H, d), 7.59 (2H, br s), 4.21 (2H, q).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52833-94-0, 2-Amino-5-bromonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; WO2015/162456; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13362-26-0, 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. 13362-26-0, name is Ethyl 2-aminonicotinate, molecular formula is C8H10N2O2, 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 ethyl 2-aminopyridine-3-carboxylate (1) (4.28 g, 25.8 mmol, Zhou, Z. L and al. Bioorg. Med. Chem. 2001, 9, 2061-2071) in 1,2-dimethoxyethane (DME) (100 mL) was added dropwise a solution of 1,1,3-trichloracetone (8.32 g, 51.5 mmol) in DME (15 mL). The mixture was stirred at room temperature for 76 h. The resulting precipitate was collected by filtration and washed with DME (2×15 mL). The solid was poured into dry ethanol (100 mL) and heated under reflux for 18 h. The cooled solution was evaporated and an aqueous saturated NaHCO3 solution (40 mL) was added. The mixture was extracted with CH2Cl2 and the organic layers were dried (MgSO4), filtered and evaporated to dryness. The residue was purified by chromatography using CH2Cl2 as eluent to give in order of elution: dichloro compound 2h (4.95 g, 70%); mp 108-110 C.; IR (KBr) 1719, 1279 cm-1; 1H NMR (200 MHz, CDCl3) delta 1.44 (t, 3H, J=7 Hz), 4.51 (q, 2H, J=7 Hz), 6.99 (t, 1H, J=7 Hz), 7.12 (s, 1H), 8.03 (m, 2H), 8.39 (d, 1H, J=7 Hz); 13C NMR (100 MHz, CDCl3) delta 14.3, 62.0, 65.3, 112.0, 112.7, 120.3, 130.3, 130.7, 141.6, 146.3, 163.5. MS m/z 276 (M++4, 2), 274 (M++2, 13), 272 (M+, 17), 237 (29), 202 (63), 200 (100), 166 (27), 129 (47).

According to the analysis of related databases, 13362-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Universite D’Auvergne Clermont 1; Universite Francois Rabelais Tours; Katholieke Universiteit Leuven; US2010/93781; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 101083-92-5, 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. 101083-92-5, name is 5-Nitro-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below.

2.675 g 5-Nitro-lH-pyrrolo[2,3-b]pyridine in 200 ml THF were hydrogenated over 1.0 g Platinum on carbon at atmospheric pressure for 3 hrs at RT (with thin layer chromatography (TLC) control). The catalyst was removed by filtration, the filtrate was evaporated and the residue purified by chromatography on silica in ethyl acetate /heptane mixtures. Yield 1.84 g

At the same time, in my other blogs, there are other synthetic methods of this type of compound,101083-92-5, 5-Nitro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/28617; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem