Category: pyridine-derivatives

Electric Literature of 1824-81-3, Adding some certain compound to certain chemical reactions, such as: 1824-81-3, name is 2-Amino-6-picoline,molecular formula is C6H8N2, 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 1824-81-3.

(A) 5-iodo-6-methylpyridin-2-amine (0307) To a solution of 6-methylpyridin-2-amine (10 g, 0.092 mol) in DMF (50 mL) was added N-iodosuccinimide (15 g, 0.13 mol), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with water (200 mL), and the precipitated solid was collected by filtration and washed with ethyl acetate to give the title compound (7.5 g). MS: [M+H]+ 235.0

According to the analysis of related databases, 1824-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1173081-96-3, 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.1173081-96-3, name is 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one hydrochloride, molecular formula is C8H13ClN2O, molecular weight is 188.6546, as common compound, the synthetic route is as follows.

Ozone was bubbled through a cooled (-78 C.) solution of methyl 3-(propan-2-yloxy)-2-(prop-2-en-1-yloxy)benzoate (123d, 438.1 mg, 1.75 mmol) in dichloromethane (17.5 mL) until a persistent violet-blue color was obtained (about 5 minutes). Nitrogen was bubbled into the solution for 3 minutes, causing the color to fade, then dimethyl sulfide (1.0 mL, 13.5 mmol) was added and the mixture allowed to warm to room temperature for one hour. The solvents were evaporated and the residue partitioned between sodium carbonate solution (sat., aq., 10 mL) and ethyl acetate (2*20 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under vacuum to give the crude residue. This crude aldehyde was dissolved in methanol (10.0 mL) and treated with 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one hydrochloride (Cpd V, 334 mg, 1.87 mmol) at room temperature for five minutes, then sodium cyanoborohydride (332 mg, 4.50 mmol) was added and the mixture stirred at room temperature for 14.5 hours. The solvents were evaporated under vacuum and the residue partitioned between deionized water (10 mL) and ethyl acetate (2*20 mL). The combined organic extracts were dried over magnesium sulfate, filtered, concentrated under vacuum, and purified by column chromatography (EtOH+5% NH4OH in ethyl acetate) to give methyl 2-(2-{[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]amino}ethoxy)-3-(propan-2-yloxy)benzoate (123e, 76 mg, 11% yield) as a colorless glass.

Statistics shows that 1173081-96-3 is playing an increasingly important role. we look forward to future research findings about 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one hydrochloride.

Reference:
Patent; PFIZER INC.; EDWARDS, Martin Paul; KUMPF, Robert Arnold; KUNG, Pei-Pei; MCAPLINE, Indrawan James; NINKOVIC, Sacha; RUI, Eugene Yuanjin; SUTTON, Scott Channing; TATLOCK, John Howard; WYTHES, Martin James; Zehnder, Luke Raymond; US2014/179667; (2014); 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. 193537-14-3, name is Ethyl 6-Boc-2-amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3-carboxylate. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

Phenylacetyl chloride (81 muL, 0.614 mmol) was added dropwise to a solution containing 9g (100 mg, 0.307 mmol) and DIPEA (59 muL, 0.34 mmol) in CH2Cl2 (2 mL), and the reaction was stirred for 2 days. The reaction solution was washed with 0.1M HCl and 1M NaOH. The organic layer was concentrated under reduced pressure and the residue was chromatographed on silica gel (hexane/Et2O 4:1) and then recrystallised from hexane (6.1 mg, 5%). 1H NMR (300 MHz, CDCl3) delta 7.45 (m, 5H, C6H5), 4.54 (s, 2H, 7-CH2), 4.29 (q, J = 7.1 Hz, 2H, CH2CH3), 3.87 (s, 2H, CH2Ph), 3.68 (m, 2H, 5-CH2), 2.90 (m, 2H, 4-CH2), 1.53 (s, 9H, Boc), 1.37 (t, J = 7.2 Hz, 3H, CH2CH3). ESI-MS m/z 445.3 [M + H]+.

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, 193537-14-3, Ethyl 6-Boc-2-amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3-carboxylate.

Reference:
Article; Nankervis, Jacob L.; Feil, Susanne C.; Hancock, Nancy C.; Zheng, Zhaohua; Ng, Hooi-Ling; Morton, Craig J.; Holien, Jessica K.; Ho, Patricia W.M.; Frazzetto, Mark M.; Jennings, Ian G.; Manallack, David T.; John Martin; Thompson, Philip E.; Parker, Michael W.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 23; (2011); p. 7089 – 7093;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6293-56-7 ,Some common heterocyclic compound, 6293-56-7, molecular formula is C7H9NO, 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.

o) 4-(2,3-Dimethylindol-5-ylamino)-7-hydroxy-6-methoxyquinazoline (68 mg, 0.2 mmol) was reacted with 3-(2-hydroxyethyl)pyridine (35 mg) to give 4-(2,3-dimethylindol-5-ylamino)-6-methoxy-7-(2-(3-pyridyl)ethoxy)quinazoline. 1H NMR Spectrum: (DMSOd6) 2.15 (s, 3H), 2.32 (s, 3H), 3.15 (t, 2H), 3.95 (s, 3H), 4.4 (t, 2H), 7.2 (s, 1H), 7.22 (d, 1H), 7.3 (dd, 1H), 7.35 (dd, 1H), 7.55 (s, 1H), 7.8 (d, 1H), 7.85 (s, 1H), 8.32 (s, 1H), 8.45 (dd, 1H), 8.6 (s, 1H), 9.4 (s, 1H), 10.68 (s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6293-56-7, its application will become more common.

Reference:
Patent; AstraZeneca AB; EP1154774; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 76041-72-0 ,Some common heterocyclic compound, 76041-72-0, molecular formula is C6H4F3NS, 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.

Intermediates 4: a) 5-Trifluoromethyl-pyridine-2-sulfonyl chloride (4a); 0.8 g (4.47 mmol) of 5-trifluoromethyl-pyridine-2-thiol is placed at -8C in 16 m L of H2S04. 16.96 mL (35.7 mmol) of a 13% sodium hypochlorite solution is poured gently such that the temperature of the reaction medium does not exceed 5C. This mixture is then stirred for 45 min, taken up by water and then extracted using AcOEt. After drying followed by reduction to dryness of the organic phases, an oil is isolated (yield: 79%) and used as such for the next reactions.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76041-72-0, its application will become more common.

Reference:
Patent; PIERRE FABRE MEDICAMENT; DUPONT-PASSELAIGUE, Elisabeth; LE ROY, Isabelle; PIGNIER, Christophe; WO2012/69503; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19798-80-2 , The common heterocyclic compound, 19798-80-2, name is 4-Chloropyridin-2-amine, molecular formula is C5H5ClN2, 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.

N-Iodosuccinimide (9.10 g, 40.4 mmol) was added to a solution of 2-amino-4-chloropyridine 29 (4.00 g, 31.1 mmol) in DMF (40 mL). The reaction mixture was stirred at room temperature for 18 h and partitioned between EtOAc (150 mL) and aqueous sodium thiosulfate solution (1M, 100 mL). The organic fraction was separated, washed successively with water (2 ¡Á 100 mL) and brine (50 mL), dried (MgSO4) and reduced in vacuo to give the crude product as a light orange solid. Column chromatography (SiO2), eluting with 5:1 Petrol-EtOAc to 2:1 Petrol-EtOAc, afforded the title compound16 (4.65 g, 18.4 mmol, 60%) as colourless needles, m.p. 117-120 C (from EtOH-water); Rf 0.57 (1:1 Petrol-EtOAc); (Found: C, 24.1; H, 1.50; N, 11.4; C5H4ClIN2 requires C, 23.6; H, 1.55; N, 11.0%); deltaH (300 MHz, DMSO-d6); 8.21 (1H, s, 6-H), 6.69 (1H, s, 3-H), 6.43 (2H, br s, 2-NH2); deltaC (75 MHz, DMSO-d6); 160.8 (2-C), 156.2 (6-C), 146.3 (4-C), 108.7 (5-C), 79.4 (3-C); numax/cm-1 (solid); 3436, 3284, 3121, 1629 and 1576; m/z (ES) 254.8 (100%, MH+); (Found MH+, 254.9182. C5H4ClIN2 requires MH 254.9180); LC-MS; RT= 1.37min, m/z (ES+) found MH+, 254.8.

The synthetic route of 19798-80-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yule, Ian A.; Czaplewski, Lloyd G.; Pommier, Stephanie; Davies, David T.; Narramore, Sarah K.; Fishwick, Colin W.G.; European Journal of Medicinal Chemistry; vol. 86; (2014); p. 31 – 38;,
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. 136117-74-3, name is Imidazo[1,2-a]pyridine-8-carbaldehyde. A new synthetic method of this compound is introduced below., Recommanded Product: 136117-74-3

Intermediate 5 : ci&3-( Imidazol” 1.2-al pyridin-8-ylmethyl)amino”|cyclobuta nolTo an emulsion of s-3-aminocyclobutanol hydrochloride (1.254g, 10.15mmol) in DCM (15mL) was added MeOH (60mL), imidazo[l,2-a]pyridine-8-carbaldehyde (1.5g, 10.26mmol) and DIPEA (2mL, 11.45mmol) and the reaction mixture stirred at room temperature under nitrogen for 10 minutes. Sodium triacetoxyborohydride (5.4g, 25.5mmol) was then added and the reaction mixture stirred under nitrogen for 18 hours and then concentrated in vacuo. The residue was dissolved in DCM (200mL), aqueous sodium hydroxide (2M, 200mL) was added and the mixture was stirred at room temperature for 1 hour. The layers were separated and to the aqueous phase was added sodium hydroxide pellets (ca. 5g) which was then extracted with 3:1chloroform sopropanol (2 x 500mL). The combined organic extracts were dried using a hydrophobic frit, evaporated in vacuo and the residue was dissolved in DCM and purified on a silica cartridge (lOOg) using a 0-25% methanol-DCM gradient over 60 min. The product containing fractions were combined and evaporated in vacuoto give the title compound as an orange oil (2.3g).LCMS (System B): tier = 1.33 min; MH+ 218

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Reference:
Patent; GLAXO GROUP LIMITED; BIGGADIKE, Keith; BRAVI, Gianpaolo; CHAMPIGNY, Aurelie Cecile; COE, Diane Mary; NEEDHAM, Deborah; TAPE, Daniel Terence; WO2012/139963; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 99368-67-9, Adding some certain compound to certain chemical reactions, such as: 99368-67-9, name is 2-Chloro-5-nitro-3-(trifluoromethyl)pyridine,molecular formula is C6H2ClF3N2O2, 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 99368-67-9.

5. 6-Chloro-5-trifluorom.eihyl-pyridin-3-ylam.ine Heat a mixture of 2-chloro-5-nitro-3-trifluoromethyl-pyridine (2.27 g, 10 mmol), calcium chloride (1.1 g, 10 mmol) and iron powder (4.5 g) in ethanol (30 mL) and water (5 mL) at reflux for 1 hour. Cool the mixture and filter through Celite. Evaporate the filtrate, dissolve the residue in EtOAc (200 mL) and wash with saturated NaHCO3(aq) (100 mL) and brine (100 mL). Dry the organic extract over MgSO4 and remove the solvent under reduced pressure to yield the title compound.

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. 99368-67-9, 2-Chloro-5-nitro-3-(trifluoromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROGEN CORPORATION; WO2006/42289; (2006); A2;,
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. 1061357-87-6, name is 6-Bromo-4-iodonicotinonitrile. A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Bromo-4-iodonicotinonitrile

To a solution of Intermediate 10A (0.60 g, 1.94 mmol) in a mixture of toluene (10 mL) and water (2 mL) was added cyclopropylboronic acid (0.20 g, 2.33 mmol) followed by K3PO4 (0.82 g, 3.88 mmol) and the resulting mixture was degassed for 15 minutes. Palladium(II) acetate (0.05 g, 0.19 mmol) and tricyclohexylphosphine (0.11 g, 0.39 mmol) ware added. The resulting mixture was degassed again for 10 minutes and heated at 140 C for 1 h in the microwave. The reaction mixture was cooled to ambient temperature and filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep12 g, 1520% EtOAc/nHexanes) to obtain Intermediate 10 (0.10 g, 23.08 %) as a yellow solid. 1H NMR (400 MHz, DMSOd6) G^ppm 0.93 1.02 (m, 1 H), 1.04 1.13 (m, 1 H), 1.19 1.35 (m, 2 H), 2.05 2.21 (m, 1 H), 8.51 (s, 1 H), 8.75 (s, 1 H). LCMS (MethodD): retention time 2.25 min, [M+2H] 223.0.

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, 1061357-87-6, 6-Bromo-4-iodonicotinonitrile.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1570-48-5, 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. 1570-48-5, name is 1-(Pyridin-3-yl)propan-1-one, molecular formula is C8H9NO, 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.

Preparation of 2-methylcyclopropanecarboxylic acid [1-(3-pyridinyl)propylidene]hydrazide, Compound 313 A mixture of 8.0 gm (0.07 mole) of 2-methylcyclopropanecarboxylic acid hydrazide, 9.46 gm (0.07 mole) of ethyl-3-pyridyl ketone, 10 drops of glacial acetic acid and 100 ml of EtOH was refluxed 20 hr. Tlc (9:1 Skellysolve B/Ethyl acetate on silica gel) shows no remaining starting material. The reaction mixture was cooled to room temperature and evaporated in vacuo to give a liquid. The liquid solidified on standing. The solid was slurried in ether, collected and dried to give 4.77 gm (29%) of the title compound having a melting point of 137.3 C. Analysis Calcd: C, 67.51; H, 7.41; N, 18.86. Found: C, 66.99; H, 7.48; N, 18.08.

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 1570-48-5, 1-(Pyridin-3-yl)propan-1-one.

Reference:
Patent; Upjohn Company; US5011932; (1991); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem