Tag: M.W:100-200

Reference of 94170-15-7 ,Some common heterocyclic compound, 94170-15-7, molecular formula is C7H7NO2, 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.

7-(1,1-Dioxythiomorpholinyl)-2-((3S,4S)-4-isobutylpyrrol-3-yl)pyrrolo[2,1-f][1,2,4-triazine-4(3H)-one (309.1 mg) was dissolved in DCM (6 mL).4-Aldehyde-1-methylpyridine-2(1H)-one (128.9 mg, 0.94 mmol) and sodium triacetoxyborohydride (416.5 mg, 1.965 mmol),Stir at room temperature overnight,TLC monitors the reaction completely,Add saturated aqueous sodium bicarbonate (5 mL),Extracted with DCM (3 x 10 mL),Organic phase merger,Washed (2 × 5mL),Dry over anhydrous sodium sulfate,filter,concentrate,The crude product was purified by silica gel column chromatography (DCM: MeOH=100:1-20:1)Yellow solid 7-(1,1-dioxythiomorpholinyl)-2-((3S,4S)-4-isobutyl-1-((1-methyl-2-oxo-1,2-di) Hydropyridin-4-yl)methyl)pyrrolidin-3-yl)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (80.0 mg, yield:19.8%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,94170-15-7, its application will become more common.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Wang Lin; Yang Xiaoju; Tian Yuwei; (46 pag.)CN108341819; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 197376-47-9, 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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate, molecular formula is C9H10ClNO2, 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 solution of ethyl (6-chloropyridin-3-yl)acetate (2.4 g) in N,N-dimethylformamide (18 mL) was added sodium hydride (60% in mineral oil, 1.2 g) under ice-cooling, and the mixture was stirred for 40 min. To the reaction mixture was added 1,4-diiodobutane (4.3 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.75 g). (1576) MS(ESI+): [M+H]+ 253.8

According to the analysis of related databases, 197376-47-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Saitoh, Morihisa; Yogo, Takatoshi; Kamei, Taku; Tokunaga, Norihito; Ohba, Yusuke; Yukawa, Takafumi; (191 pag.)US2016/159773; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 33252-29-8, 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 33252-29-8 as follows.

Weigh 2.38 g of 2-chloro-6-cyanopyridine and 0.05 g of ETS-10 in a reaction tube.Add 50mL of water, heat up to 110 C reaction, TLC tracking detection,The reaction was completed in 22 hours, and after cooling, it was centrifuged.The resulting solution is distilled off to obtain a product2-chloro-6-pyridinecarboxamide 1.46 g, yield 94%,The purity is 99.75% (gas chromatography detection). Centrifuged solidRepeat the reaction, the reaction conditions, the amount of raw materials are the same as above, when repeated 4 times,The yield is above 90%, and the yield is 84% in the fifth reaction.The purity is 97% or more.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33252-29-8, its application will become more common.

Reference:
Patent; Wenzhou University; Xiong Jing; Hu Rongrong; Liu Wuqiang; Tao Yangyang; Feng Xiaogang; Zhou Zheng; (6 pag.)CN104072409; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 107867-51-6, Adding some certain compound to certain chemical reactions, such as: 107867-51-6, name is 5-(Trifluoromethyl)pyridine-2,3-diamine,molecular formula is C6H6F3N3, 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 107867-51-6.

To the solution of I-B (499 mg, 1.51 mmol) in DMA (2.5 mL) at -5 C was added thionyl chloride (0.14 mL, 1.9 mmol). After stirring for 40 min at -5 C, a solution of 5- (trifluoromethyl)pyridine-2,3-diamine (295 mg, 1.66 mmol) in DMA (3 mL) was added to this reaction mixture. The reaction mixture was stirred at RT for 18 h. The reaction was quenched with water and extracted with DCM. Solid precipitated out from the organic phase, which was collected via filtration to afford N-(4-(l-((2-amino-5-(trifluoromethyl)pyridin-3- yl)carbamoyl)cyclobutyl)phenyl)-3-chlorobenzamide. MS (EI) m/z 489 [M+H]+.

According to the analysis of related databases, 107867-51-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; SLOMAN, David, L.; YU, Wensheng; (98 pag.)WO2019/27855; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 25194-01-8, 2,6-Dichloro-4-nitropyridine, 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: C5H2Cl2N2O2, blongs to pyridine-derivatives compound. HPLC of Formula: C5H2Cl2N2O2

(1) Synthesis of an Intermediate, 2,6-dichloro-4-methoxypyridine To a tetrahydrofuran solution containing methanol (0.37 g, 0.0104*1.1 mol), sodium hydride (0.44 g (ca. 60% in mineral oil), 0.0104*1.05 mol) was added, then 2,6-dichloro-4-nitropyridine (2.00. g, 0.0104 mol) was added thereto and the resultant solution was stirred for about 2 hours at room temperature. After it was confirmed that there was no bubbling with the addition of methanol (1.0 g, 0.0355*0.9 mol), the resultant solution was stirred for about another 1 hour. After the reaction solution was partitioned between ethyl acetate and water, the obtained organic layer was washed successively with aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and thereafter concentrated to obtain the substantially pure end product. Yield: 1.63 g (88%). Solid. Melting point: 94 to 96 C. 1 H-NMR (60 MHz, CDCl3, delta): 3.79(3H, s), 6.70(2H, s).

The synthetic route of 25194-01-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kureha Kagaku Kogyo Kabushiki Kaisha; US5691277; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 87674-21-3, 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.87674-21-3, name is 1-(3-Fluoropyridin-4-yl)ethanone, molecular formula is C7H6FNO, molecular weight is 139.13, as common compound, the synthetic route is as follows.

To a stirred solution of 3-FLUORO-4-ACETYLPYRIDINE (5.3 g, 38.1 MMOL) in glacial acetic acid (14 mL) and 48% HYDROBROMIC acid (5.3 mL), bromine (2 mL, 38 MMOL) in glacial acetic acid (5.3 mL) was added slowly and dropwise. After addition, the solution was stirred at 60C for 2.5 h then it was cooled down and ethylacetate (70 mL) was added. After 30’stirring the mixture was filtered and the solid was washed thoroughly with ethylacetate and dried. The title compound was obtaind in 82% yield (9.4 g). ‘H NMR (DMSO-D6/300 MHz) 5 ppm 4.88 (s, 2 H) 7.83 (dd, 1 H) 8.62 (DD, 1 H) 8.81 (d, 1 H).

The chemical industry reduces the impact on the environment during synthesis 87674-21-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PHARMACIA ITALIA S.P.A.; WO2005/13986; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58481-17-7, 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 58481-17-7 as follows.

A. methyl 2-formylpyridine-4-carboxylate To a solution of methyl 2-(hydroxymethyl)pyridine-4-carboxylate (30 g, 179.64 mmol) in DCM (1 L) was added MnO2 (93.77 g. 1.0778 mol) at r.t. and stirred overnight. The reaction mixture was then filtered and concentrated to afford the title compound (21.3 g, 72%). [M+H] Calc’d for C8H7NO3, 166. Found, 166.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58481-17-7, its application will become more common.

Reference:
Patent; Quanticel Pharmaceuticals, Inc.; Kanouni, Toufike; Nie, Zhe; Stafford, Jeffrey Alan; Veal, James Marvin; US2014/275084; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58602-02-1, Adding some certain compound to certain chemical reactions, such as: 58602-02-1, name is 2,6-Difluoro-3-nitropyridine,molecular formula is C5H2F2N2O2, 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 58602-02-1.

Synthesis of 2,6-difluoro-3-aminopyridine 2,6-Difluoro-3-nitropyridine (3.84 g) was dissolved in ethanol (42 ml). A solution of iron powder (4.03 g) and ammonium chloride (2.57 g) in water (14 ml) was added, and the reaction solution was heated and stirred at 80C for one hour. After leaving to cool, the reaction solution was filtered through celite. Ethyl acetate and water were added and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (2.06 g). The property values of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 3.66 (brs, 2H), 6.65 (dd, J=8.2, 3.0Hz, 1H), 7.22 (ddd, 10.4, 8.2, 6.8Hz, 1H).

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. 58602-02-1, 2,6-Difluoro-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2181992; (2010); 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. 23628-31-1, name is 6-Aminopicolinic acid, the common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Aminopicolinic acid

To a solution of 2-amino-6-pyridinecarboxylic acid (90; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 0 0C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate 91 (5.5 g, 76%).

The synthetic route of 23628-31-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; VU, Chi, B.; DISCH, Jeremy, S.; NG, Pui, Yee; BLUM, Charles, A.; PERNI, Robert, B.; WO2010/3048; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 36178-05-9, 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. 36178-05-9, name is 3-Bromo-2-fluoropyridine, molecular formula is C5H3BrFN, 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.

A 60% dispersion of sodium hydride in mineral oil (7.4 g, 184.6 mmol) was suspended in anhydrous tetrahydrofuran (300 mL) under nitrogen. Absolute ethanol (10.0 mL, 170.4 mmol) was added dropwise at room temperature and the reaction mixture was stirred for 40 minutes at room temperature. 2-Fluoro-3-bromopyridine (25.0 g, 142.0 mmol) was added and the reaction mixture was stirred for 3 hours at room temperature. Water (250 mL) was added and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (2 x 200 mL). The organic layers were combined, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a light yellow oil (31 .5 g, 84%). 1H NMR (400MHz, CDCl3): delta ppm 1.43 (m, 3H), 4.43 (m, 2H), 6.74 (m, 1 H), 7.79 (m, 1 H), 8.07 (m, 1 H). LCMS Rt = 2.45 minutes MS m/z 203 [MH]+

According to the analysis of related databases, 36178-05-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; STORER, Robert, Ian; SWAIN, Nigel, Alan; WO2013/93688; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem