Tag: M.W:100-200

Electric Literature 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.

To a solution of 1 (50 mg, 0.071 mmol) in 354 ml of pyridine at room temperature was added nicotinoyl chloride hydrochloride (15 mg, 0.085 mmol) followed by triethylamine (23 ml, 0.170 mmol). After stirring for 1.5 h, 4-dimethylamino pyridine (8.6 mg, 0.071 mmol) was added. After stirring 5 h, additional triethylamine (23 ml, 0.170 mmol), 4-dimethylamino pyridine (8.6 mg, 0.071 mmol), and nicotinoyl chloride hydrochloride (15 mg, 0.085 mmol) was added along with a 50 ml pyridine rinse. After stirring 18 h the reaction was treated with 0.5 ml of saturated aqueous sodium bicarbonate and washed with methylene chloride (4×1 ml). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to a light brown oil. Chromatography (14 g of flash silica gel), eluting with ethyl acetate-hexanes (10:1) provided 49 mg (85%) of the free base as a white foam. The nicotinoate was dissolved in 1 ml of methylene chloride and treated with a 1.0 M solution of hydrogen chloride in diethyl ether (90 ml, 0.090 mmol). The clear, colorless solution was allowed to stand at room temperature for 5 min. Removal of the solvent in vacuo produced 51 mg of the title compound as a white foam: 500 MHz 1H NMR (CDCl3) d 8.94 (s, 1H), 8.78 (br s, 1H), 8.29 (d, 1H, J=7.0 Hz), 7.57 (br s, 1H), 7.38 (d, 2H, J=7.1 Hz), 7.30-7.16 (m, 5H), 7.10 (dd, 1H, J=8.4, 1.7 Hz), 6.88 (d, 1H, J=8.4 Hz), 6.71 (m, 1H), 5.80 (d, 1H, J=15 Hz), 5.74 (d, 1H, J=9.6 Hz), 5.56 (br s, 1H), 5.00 (d, 1H, J=9.6 Hz), 4.95 (t, 1H, J=8.9 Hz), 4.84 (d, 1H, J=9.8 Hz), 4.77-4.72 (m, 1H), 3.91 (s, 3H), 3.39 (dd, 1H, J=13, 8.2 Hz), 3.23-3.14 (m, 2H), 3.06 (dd, 1H, J=14, 7.6 Hz), 2.81-2.74 (m, 1H), 2.62-2.45 (m, 2H), 1.93 (ddd, 1H, J=14, 12, 4.8 Hz), 1.78-1.70 (m, 1H), 1.66-1.59 (m, 1H), 1.25 (s, 3H), 1.20 (d, 3H, J=7.0 Hz), 1.19 (s, 3H), 0.98 (d, 3H, J=6.7 Hz), 0.84 (d, 3H, J=6.5 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20260-53-1, Nicotinoyl chloride hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; Wayne State University; University of Hawaii; US6680311; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 67367-26-4 ,Some common heterocyclic compound, 67367-26-4, molecular formula is C8H9NO3, 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.

In a 250 mL dry round bottom flask with a reflux condenser and magnetic stirrer was placed with 2-chloro-3-ethyl nicotinate (12.0 g, 64.7 mmol) in dry methanol (200 mL), and CH3ONa (21 mL, 97.0 mmol, 25% in methanol) were added slowly and the reaction mixture was refluxed for 16 hour. The reaction mixture was cooled to room temperature and quenched by addition of a saturated aqueous NH4CI solution and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give 2-methoxy-3-methyl nicotinate (10.0 g, 93%). In a dry 500 mL round bottom flask NaH (549 mg, 13.7 mmol, 60% in mineral oil) was added in DMF (10 mL). Acetophenone (1.5 g, 12.5 mmol) in dry DMF (10 mL) was added drop-wise at O0C in 30 min. The reaction mixture was stirred for 1 h at room temperature. 2- Methoxy-3-m ethyl nicotinate (2.08 g, 12.5 mmol) dissolved into dry DMF (10 mL) was added slowly on cooling. After addition the mixture was stirred for 16 h at EPO room temperature. The reaction mixture was quenched by addition of a saturated aqueous NH4CI solution and diluted with water. The solid was filtered off, washed with water and dried to give the diketo product (2.94 g, 92%). Poly phosphoric acid (15.0 g) was heated at 9O0C and the diketo compound (1.5 g, 3.50 mmol) was added slowly and heated at 9O0C for 1 hours. The reaction mixture was cooled to room temperature and diluted with water. The solid was separated by filtration, washed with water and dried to give pure 2-phenyl-4H-pyrano[2,3- b]pyridin-4-one (655 mg, 50%); MS (ES) m/z: 224.94 (M+1 ), 223.95 (M); MP 103- 1050C

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67367-26-4, its application will become more common.

Reference:
Patent; RESVERLOGIX CORP.; JOHANSSON, Jan, O.; HANSEN, Henrik, C.; CHIACCHIA, Fabrizio, S.; WONG, Norman, C.W.; WO2007/16525; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13362-78-2, (E)-1,2-Di(pyridin-4-yl)ethene, 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, Formula: C12H10N2, blongs to pyridine-derivatives compound. Formula: C12H10N2

A mixture of Zn(NO3)26H2O (0.3 g, 1 mmol), H3tris (0.24 g,2 mmol), and bis(4-pyridyl)ethylene (0.18 g, 1 mmol) inmethanol (20 mL) was sealed in a Teflon-lined stainless steelcontainer and heated at 110 C for 30 hours, then slowlycooled to room temperature. The resulted yellow crystals werewashed with methanol and dried in air. Yield: 68percent.

The synthetic route of 13362-78-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cucos, Andrei; Paraschiv, Carmen; Shova, Sergiu; Madalan, Augustin; Sbarcea, Gabriela; Marinescu, Virgil; Andruh, Marius; Revue Roumaine de Chimie; vol. 60; 10; (2015); p. 1005 – 1013;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1101120-05-1, 3-Formylpyrazolo[1,5-a]pyridine-5-carbonitrile, 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, Formula: C9H5N3O, blongs to pyridine-derivatives compound. Formula: C9H5N3O

General procedure: A solution of the aldehyde or ketone (1 equiv) and 2-methyl-5-nitrobenzenesulfonohydrazide (1.1 equiv) in MeOH (5 mL) was refluxed for 18 h unless otherwise stated. After cooling to room temperature, the precipitated solid was filtered off, washed with a little MeOH and dried.

The synthetic route of 1101120-05-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 69 – 85;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59782-85-3, 2,5-Dichloronicotinic 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, Formula: C6H3Cl2NO2, blongs to pyridine-derivatives compound. Formula: C6H3Cl2NO2

Description 97: methyl 4-(1-(2,5-dichloronicotinamido)cyclopropyl)benzoate (D97)To a solution of 2,5-dichloronicotinic acid (1 .84g, 7.06 mmol) in dry dimethylformamide (15ml) 1 -Hydroxybenzotriazole hydrate (1 .08 g, 7.06 mmol) and 1 -ethyl-3-(3-dimethylaminopropyl) carbodiimide (2.03g, 10.58 mmol), a solution of methyl 4-(1 -aminocyclopropyl)benzoate hydrochloride (D7) (1 .67g, 7.06 mmol) and triethylamine (0.98ml, 7.06 mmol) in dry dimethylformamide (15ml) was added and the resulting mixture was stirred 1 h at room temperature. NH4CI saturated solution (50ml) was added the mixture was extracted with ethylacetate (3x50ml). Collected organics, after solvent evaporation, was purified by Biotage column SNAP-Si (50g) eluting with a mixture dichloromethane/ ethylacetate from 100/0 to 95:5. Collected organics after solvent evaporation afforded the title compound (D97) (1 .03 mg)MS: (ES/+) m/z: 365.1 [MH+] C17H14CI2N203 requires 364.41 H NMR (400MHz ,CHLOROFORM-d) delta = 8.46 (d, J = 2.4 Hz, 1 H), 8.14 (d, J = 2.4 Hz, 1 H), 8.05 – 7.99 (m, 2 H), 7.41 – 7.35 (m, 2 H), 7.17 (s, 1 H), 3.93 (s, 3 H), 1 .50 (s, 4 H).

The synthetic route of 59782-85-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); 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.13143-47-0, name is 1-(4-Aminophenyl)-1H-pyridin-2-one, molecular formula is C11H10N2O, molecular weight is 186.21, as common compound, the synthetic route is as follows.Quality Control of 1-(4-Aminophenyl)-1H-pyridin-2-one

Step 2: To a solution of compound 12.2 (7.44 g, 40 mmol) in 100 mL DMF was added NBS(14.2 g, 80 mmol) in small portions. The mixture was stirred at RT overnight. It was diluted with 1000 mL ethyl acetate, washed with brine three times, dried, concentrated and subjected to flash column chromatography using 5 % methanol in DCM to isolate compound 12.3 (7.20 g, 68 %). MS found for C11H9BrN2O (M+H)+ 265.0, 267.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13143-47-0, 1-(4-Aminophenyl)-1H-pyridin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; SCARBOROUGH, Carroll; WO2008/86226; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884495-22-1, 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.884495-22-1, name is 5-Bromo-2-fluoropyridin-3-amine, molecular formula is C5H4BrFN2, molecular weight is 191.0011, as common compound, the synthetic route is as follows.

General procedure: To a solution of 76 (120 mg, 0.37 mmol) in dry pyridine (12 mL) under N2 at RT, was added 2,4-difluorobenzenesulphonyl chloride (159 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) dropwise over 5 min. The mixture was stirred at 45 C under N2 for 16 , and the solvent then removed under reduced pressure. The reaction was quenched with a little water and the resulting solid collected by filtration and washed with water and Et2O. Purification was carried out by trituration with hot CH2Cl2/MeOH solution to give 4 as a pale brown solid (65%).

The chemical industry reduces the impact on the environment during synthesis 884495-22-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 139 – 155;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 5398-44-7, 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.5398-44-7, name is 2,6-Dichloroisonicotinic acid, molecular formula is C6H3Cl2NO2, molecular weight is 192, as common compound, the synthetic route is as follows.

a) A suspension of 2,6-dichloroisonicotinic acid (5.23 g, 27.24 mmol) in toluene (100 ml.) is heated to 800C and then slowly treated with N,N-dimethylformamide di-tert. butylacetal (19.94 g, 98.0 mmol). The mixture becomes slightly yellow and clear. Heating and stirring is continued for 3 h before the solution is cooled to rt, diluted with ether and washed with sat. aq. Na2CO3-solution. The org. extract is dried over MgSO4, filtered and the solvent is evaporated to give 2,6-isonicotinic acid tert.-butyl ester (6.97 g) which solidifies as beige fine needles. 1 H NMR (CDCI3): delta 1.60 (s, 6 H), 7.73 (s, 1 H).

Statistics shows that 5398-44-7 is playing an increasingly important role. we look forward to future research findings about 2,6-Dichloroisonicotinic acid.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2008/29371; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 99163-12-9, 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 99163-12-9, name is 4-Pyridin-4-yl-benzaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

25 g (110 mmol) of N-(4-chlorophenyl)-1 ,2-phenylene diamine and 20 g (110 mmol) of biphenyl-4-carboxaldehydewere agitated with 300 mE of 2-methoxy ethanol in a 2000 mE round flask, the temperature of the reaction vessel was increased up to a reflux temperature, and the resultant was agitated for 24 hours. The reaction solution was treated with methylene chloride and water to obtain an organic layer, andanhydrous magnesium sulfate was used to remove moisturefrom the organic layet 12 g of a compound (D) (28% yield)was obtained by colunmizing the resultant after removing asolvent therefrom.Atomic analysis of the compound (D) was performed, andthe results are provided as follows.calcd. C24H16C1N3: C, 75.49; H, 4.22; N, 11. found: C, 75.79; H, 4.11; N, 11.8.

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 99163-12-9, 4-Pyridin-4-yl-benzaldehyde.

Reference:
Patent; CHEIL INDUSTRIES, INC.; Park, Moo-Jin; Yu, Eun-Sun; Chae, Mi-Young; (64 pag.)US9444054; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 932-35-4, 3-Hydroxypicolinonitrile, 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, Recommanded Product: 932-35-4, blongs to pyridine-derivatives compound. Recommanded Product: 932-35-4

[00181] To a solution of isopropyl 4-(4-chloro-leta-pyrazolo[3,4-d]pyrimidin-l- yl)piperidine- 1 -carboxylate from Example 19C (63 mg, 0.195 mmol) in 2 mL of DMF was added 3-hydroxypicolinonitrile (23.37 mg, 0.195 mmol) and potassium carbonate (53.8 mg, 0.389 mmol). The reaction was allowed to stir at room temperature for 18 h. The reaction was diluted with ethyl acetate, washed with sat’d aq sodium bicarbonate and brine, dried over MgSO4, filtered through a pad of silica gel and concentrated in vacuo to an oil. The residue was purified by silica gel chromatography (12 g ISCO cartridge, 0-90% ethyl acetate/hexane, 15 min gradient) to afford Example 19 (24 mg, 29%) as an off-white solid. 1H NMR (500 MHz, CDCl3) delta ppm 1.29 (d, J=6.05 Hz, 6 H) 2.02 – 2.08 (m, 2 H) 2.25 – 2.35 (m, 2 H) 2.98 – 3.08 (m, 2 H) 4.38 (s, 2 H) 4.94 – 5.05 (m, 2 H) 7.68 (dd, J=8.52, 4.67 Hz, 1 H) 7.88 (d, J=8.80 Hz, 1 H) 8.27 (s, 1 H) 8.49 (s, 1 H) 8.69 (d, J=4.40 Hz, 1 H). LRMS (ESI): 408.3 (M+H)+.

The synthetic route of 932-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/137436; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem