Tag: M.W:100-200

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.802325-29-7, name is (5-Fluoropyridin-2-yl)methanol, molecular formula is C6H6FNO, molecular weight is 127.12, as common compound, the synthetic route is as follows.Quality Control of (5-Fluoropyridin-2-yl)methanol

To a stirred solution of (5-fluoropyridin-2-yl)methanol (500 mg, 3.937 mmol, commercial source: Combi-Blocks) and triethylamine (398 mg, 3.937 mmol) in /V,/V-dimethylformamide (10 ml_), mesyl chloride (451 mg, 3.937 mmol) was added at 27 C. The reaction mixture was stirred at 27 C for 2 h. Followed by the addition of sodium azide (384 mg, 5.905 mmol) at 27 C and the reaction mixture was stirred for 12 h at the same temperature. Upon completion, the reaction mixture was concentrated under reduced pressure. The crude compound was purified by column chromatography (silica gel 100-200 mesh) using 5% ethyl acetate in pet ether. The pure fractions were collected and concentrated under reduced pressure to afford 2-(azidomethyl)-5- fluoropyridine (150 mg, 25%) as a brown liquid. NMR (400 MHz, CDCI3) 5 8.46 (d, J = 2.6 Hz, 1 H), 7.47-7.40 (m, 1 H), 7.39-7.33 (m, 1 H), 4.48 (s, 2H). MS m/z [M+H]+= 153.12.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,802325-29-7, (5-Fluoropyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ALEMPARTE-GALLARDO, Carlos; ENCINAS, Lourdes; ESQUIVIAS PROVENCIO, Jorge; (206 pag.)WO2019/34729; (2019); 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. 1570-48-5, name is 1-(Pyridin-3-yl)propan-1-one. A new synthetic method of this compound is introduced below., Safety of 1-(Pyridin-3-yl)propan-1-one

A solution of the 3-propionylpyridine (5g, 37 mmol) , (S)-(-)-2-methylpropane-2- sulfinamide (4.7 g, 38.8 mmol) and titanium (IV) ethoxide (17.8g, 78 mmol) in THF (100 mL) was heated at 80C for 3 days. After cooling, brine (100 mL) and EA (100 mL) were added. The mixture was stirred at RT for 1 h. The mxture was filtered through Celite, and the pad was washed with EA. The organic phase was seperated, concentrated, and the residue was chromatographed (eluted with 2:1 hexane:EA) to give the product as a colorless oil (8.15g, 92%).

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

Reference:
Patent; EXITHERA PHARMACEUTICALS, INC.; CHENARD, Bertrand, L.; XU, Yuelian; STASSEN, Frans, L.; HAYWARD, Neil, J.; (225 pag.)WO2018/118705; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14150-94-8, 1-Methyl-3,5-dinitro-1H-pyridin-2-one, 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: C6H5N3O5, blongs to pyridine-derivatives compound. HPLC of Formula: C6H5N3O5

11.2 (3-Nitro-5,6,7,8-tetrahydro-quinolin-5 and 7-yl)-carbamic acid benzyl ester; A mixture of 1-methyl-3,5-dinitro-2-pyridone (3.66 g, 18.38 mmol) and (3-oxo- cyclohexyl)-carbamic acid benzyl ester (4.55 g, 18.39 mmol) in methanolic am¬ monia (1 M1 140 ml) was heated at 65C for 1.5 h. It was then concentrated and digested in CH2CI2. The organic layer was washed with H2O (x2), dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel (heptane:ethyl acetate, 3:1) to afford a mixture 1/2 of the 5 and 7 regioisomers (4.51 g, 75% for two steps) as a pale yellow gum. MS (ESI+) m/z = 328.1 [M+H]+ 1H NMR (400 MHz, CDCI3) : delta (ppm) 1.83 (m, 1.5H), 2.01 (m, 1H), 2.20 (m, 1.5H), 2.90 (dd, J = 18.1 , 8.7 Hz1 1H), 3.00 (t, J = 6.4 Hz1 2H), 3.05 (t, J = 6.4 Hz, 1 H)13.43 (dd, J = 18.1 , 5.2 Hz1 1H)1 4.16 (m, 1H)1 4.81 (bs, 1 H)1 5.03 (bs, 1H), 5.12 (s, 2H), 5.19 (s, 1 H), 7.36 (m, 7.5 H)1 8.19 (bs, 1H), 8.46 (bs, 0.5H)1 9.20 (d, J = 1.9 Hz, 1 H), 9.23 (d, J = 2.1 Hz1 0.5H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14150-94-8, 1-Methyl-3,5-dinitro-1H-pyridin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; ABBOTT GMBH & CO.KG; WO2006/40178; (2006); 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. 1990-90-5, name is 3-Methylpyridin-4-amine, the common compound, a new synthetic route is introduced below. COA of Formula: C6H8N2

To a solution of 2-(5-chloro-2-fluorophenyl)-4-iodo-5-methyl-6,7-dihydro-5H-cyclo- pentapyrimidine (275 mg, 0.71 mmol, 1 eq) in dioxane (5 ml) was added Pd(OAc)2 (8 mg, 0.04 mmol, 0.05 eq) followed by BINAP (33 mg, 0.05 mmol, 0.075 eq), 4-amino-3-picoline (84 mg, 0.78 mmol, 1.1 eq) and Cs2CO3 (347 mg, 1.06 mmol, 1.5 eq). The reaction mixture was heated to 80C for 15 h. The reaction mixture was cooled to r.t. and filtered through Celite and the crude material was purified by flash column chromatography (l:l/ethyl acetate:hexane-100% ethyl acetate) to afford [2-(5-chloro-2-fluorophenyl)-5-methyl-6,7-dihydro-5H-cyclopentapyrimidin-4-yl]- (3-methyl-pyridin-4-yl)-amine, compound of formula (43) (250 mg, 96%)

The synthetic route of 1990-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2006/35061; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 98549-88-3, 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.98549-88-3, name is 1H-Pyrrolo[2,3-b]pyridin-5-ol, molecular formula is C7H6N2O, molecular weight is 134.14, as common compound, the synthetic route is as follows.

Example 724-[4-(1H-Pyrrolo[2,3-b]pyridin-5-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester; A mixture of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 50 mg, 0.15 mmol), 1H-pyrrolo[2,3-B]pyridin-5-ol (Matrix Scientific, Columbia, S.C., USA; 26 mg, 0.19 mmol), and potassium carbonate (27 mg, 0.19 mmol) in dimethylformamide (2 mL) was heated in the microwave oven at 160 C. for 10 min. Ethyl acetate and water were added, and the aqueous layer was extracted twice with ethyl acetate. The ethyl acetate layers were combined, evaporated, and purified by preparative C18 HPLC, eluting with 10-100% acetonitrile/water. Samples containing the product were extracted twice with dichloromethane and the solvent was evaporated under high vacuum to give 4-[4-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (21 mg, 33%) as a white powder. 1H NMR (300 MHz, DMSO-d6) delta 1.43 (s, 9H), 1.80-2.15 (m, 4H), 3.02 (br s, 2H), 4.08 (d, 2H, J=12.4 Hz), 4.85-5.10 (m, 1H), 6.45-6.52 (m, 1H), 7.58 (d, 1H, J=2.9 Hz), 7.94 (d, 1H, J=2.5 Hz), 8.20 (d, 1H, J=2.5 Hz), 8.22 (s, 1H), 8.50 (s, 1H), 11.85 (br s, 1H). Mass spectrum (ES) MH+=436. HRMS Calcd. for C22H26N7O3 (MH+): 436.2092. Found: 436.2090.

The chemical industry reduces the impact on the environment during synthesis 98549-88-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Erickson, Shawn David; Gillespie, Paul; Guertin, Kevin Richard; Karnachi, Prabha Saba; Kim, Kyungjin; Ma, Chun; McComas, Warren William; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Tilley, Jefferson Wright; Zhang, Qiang; US2009/286812; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 771579-27-2, 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. 771579-27-2, name is 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one, molecular formula is C8H12N2O, 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.

Carboxylic acid (13.44g, 39.4mmol) was dissolved in 70mLDMSO, and added with stirring 4,6-dimethyl-3-aminomethyl-pyridinePyridine -2 (1H) – one (12.4g, 81.9mmol). Stirred at room temperature 15min, then add hexafluorophosphate, benzotriazol-1-yl – yloxy tripyrrolidinophosphonium phosphorus (PYBOP) (31.9g, 61.4mmol), stirred at room temperature overnight, until the reaction was complete (developing solvent: ethyl acetate / ethanol = 5: 1), the reaction mixture was poured into 700mL ice water, stirred for 30min, to obtain a solid by suction filtration, washed with a 500 mL of water, and dried under vacuum dryer, the resulting solid was added with stirring acetonitrile (75mL × 2), suction, vacuum dryer. The resulting solid was combined with 100mL stirring methanol / dichloromethane (5:95), filtration, and dried under reduced pressure to obtain a solid product was thoroughly 14g, Yield 74%

According to the analysis of related databases, 771579-27-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu University of Technology; Liang, Guoping; Wang, Yazhen; Zheng, Chunzhi; Zhao, Dejian; Zhang, Jizhen; (13 pag.)CN105440023; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 69627-02-7, 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.69627-02-7, name is Thieno[3,2-b]pyridin-7(4H)-one, molecular formula is C7H5NOS, molecular weight is 151.19, as common compound, the synthetic route is as follows.

5.00 g of [3,2-b]pyridin-7-ol (33 mmol) and 50 g of phosphorus oxybromide (174 mmol) are put in a flask and heated at 1100C for 3h. The hot reaction mixture is poured into mixture of ice and 5N NaOH and extracted with CHC12, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane :AcOEt=3:l) to give 4.19 g of the title compound . Yield 59%. mass spectrum (m/e):215(M+l); IH-NMR(CDCl3): 8.55(d, IH, J=4.3Hz), 7.86(d, IH, J=5.7Hz), 7.69(d, IH, J=5.7Hz), 7.49(d, IH, J=4.3Hz) ppm.

Statistics shows that 69627-02-7 is playing an increasingly important role. we look forward to future research findings about Thieno[3,2-b]pyridin-7(4H)-one.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/107784; (2006); A1;,
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. 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, 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. Application In Synthesis of 3-(Chloromethyl)pyridine hydrochloride

General procedure: DMF (5-10 mL/mmol). K2CO3 (10 equiv) was added and the suspensionstirred for 15 min. Then, 3-(chloromethyl) pyridiniumchloride (1.1 equiv) was added and the reaction mixture was stirredfor 48 h at room temperature. The suspension was diluted withH2O and extracted with EtOAc. The combined organic phases werewashed with H2O and brine, dried over magnesium sulfate and thesolvent was removed in vacuo. The crude products were purifiedby column chromatography [Cyclohexane/EtOAc, 3:1 4.2.2.3 tert-Butyl N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-amino-pent-4-enoate (S)-Enantiomer, ((S)-15): Yield: 750 mg (55%), white solid. Mp 176-177 C. 1H NMR (300 MHz, CDCl3): delta 1.31 (s, 9H), 2.27 (ddd, 2JH,H = 14.7 Hz, 3JH,H = 8.0 Hz, 3JH,H = 6.9 Hz, 1H), 2.49 (dt, 3JH,H = 13.8 Hz, 3JH,H = 6.9 Hz, 1H), 3.86 (s, 3H), 4.49 (d, 2JH,H = 16.1 Hz, 1H), 4.51 (t, 3JH,H = 7.5 Hz, 1H), 4.69 (d, 2JH,H = 16.6 Hz, 1H), 4.89 (dd, 3JH,H = 17.1 Hz, 2JH,H = 1.5 Hz, 1H), 4.99 (dd, 3JH,H = 10.2 Hz, 2JH,H = 1.5 Hz, 1H), 5.60 (ddt, 3JH,H = 17.0 Hz, 3JH,H = 10.3 Hz, 3JH,H = 6.7 Hz, 1H), 6.94 (dm, 3JH,H = 9.0 Hz, 2H), 7.25 (dd, 3JH,H = 7.9 Hz, 3JH,H = 4.9 Hz, 1H), 7.73 (dm, 3JH,H = 9.0 Hz, 2H), 7.86 (d, 3JH,H = 7.9 Hz, 1H), 8.50 (d, 3JH,H = 4.0 Hz, 1H), 8.54 (d, 4JH,H = 1.7 Hz, 1H) ppm. 13C NMR (75 MHz, CDCl3): delta 27.8 (q), 35.5 (t), 46.6 (t), 55.6 (q), 60.2 (d), 82.3 (s), 114.1 (d), 118.4 (t), 123.3 (d), 129.6 (d), 131.5 (s), 133.0 (d), 133.7 (s), 136.6 (d), 148.5 (d), 149.0 (d), 163.0 (s), 169.3 (s) ppm. HRMS (ESI+): C22H28N2O5S+H+, calcd 433.1797, found: 433.1812; C22H28N2O5S + Na+, calcd 455.1617, found: 455.1630, (C22H28N2O5S)2+H+, calcd 865.3516, found: 865.3532; (C22H28N2O5S)2 + Na+, calcd 887.3336, found: 887.3345. Optical rotation (c 1.001, CHCl3): [alpha]58920 = -26.4, [alpha]57820 = -27.3, [alpha]54620 = -31.2, [alpha]43620 = -56.6, [alpha]36520 = -97.7.

With the rapid development of chemical substances, we look forward to future research findings about 6959-48-4.

Reference:
Article; Behrends, Malte; Wagner, Stefan; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Kumbhar, Sadhana; Waller, Mark; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3809 – 3818;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6980-08-1, Adding some certain compound to certain chemical reactions, such as: 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine,molecular formula is C5H4ClN3O2, 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 6980-08-1.

4-Chloro-3-nitropyridin-2-amine (0.1 0 g, 0.58 mmol) was dissolved in dryacetonitrile (20 ml). To the stirred solution was then added N-bromosuccinimide (0.124g, 0.70 mmol), and the reaction mixture was heated at 80 C for 1 h. Volatiles wereremoved in vacuo and the residue purified by silica column chromatography (elution with25 dichloromethane) to provide the title compound as a pale brown powder (0.125 g, 85%).1 H-NMR (500 MHz, DMSO-d6) 7.35 (s, 2H, NH2), 8.41 (s, 1 H, 6-H).

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. 6980-08-1, 4-Chloro-3-nitropyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BLAGG, Julian; BAVETSIAS, Vassilios; MOORE, Andrew S.; LINARDOPOULOS, Spyridon; WO2013/190320; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 929022-76-4, 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 929022-76-4, name is 2-Chloro-4-fluoronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Step B: Ethyl (2-chloro-4-fluoropyridin-3-yl)acetate (64-3)Intermediate 64^2 (19.9g, 108 mmol) was dissolved in CH2C12 (100 ml), added lml DMF and then added oxalyl chloride (17.2 g, 135 mmol) dropwise over 10 minutes. When gas evolution subsided (about an hour), the reaction was concentrated and azeotroped with THF (3 x 50 ml) to give the crude acid chloride. TMS-diazomethane solution (97 ml, 2.0 M, 195 mmol) was added to 300 ml 1 : 1 THF/CH3CN and then cooled to 0C. NEt3 (27.2 ml, 195 mmol) was added and then the acid chloride was added dropwise over 20 minutes. Stirred for 1 hour at 0C and then stored in freezer (-4C) overnight. Diluted with EtOAc and then washed with ¾0; added 0.5 N HCl to organic portion, stirred 5 minutes, basified with 1 N NaOH. Organic portion separated, washed with brine, dried (MgS04) and concentrated. Dissolved residue in EtOH (300 ml), added NEt3 (18.1 ml, 130 mmol) followed by portionwise addition of silver benzoate (3.72 g, 16.24 mmol, gas evolution). Heated to 80C for 10 minutes and then allowed to cool to ambient. The mixture was concentrated. Diluted with CH2Ci2, filtered and concentrated. The residue was purified by column chromatography on silica gel, eluting with hexanes to EtOAc to give 64-3 (8.05 g. 34.2%) as a colorless oil MS (ESI): m/z = 218.0 (MH+).

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 929022-76-4, 2-Chloro-4-fluoronicotinic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BUNGARD, Christopher, James; PERKINS, James, J.; MANIKOWSKI, Jesse, J.; DE LEON, Pablo; MEISSNER, Robert, S.; WO2011/53574; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem