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.100-55-0, name is 3-Pyridinemethanol, molecular formula is C6H7NO, molecular weight is 109.13, as common compound, the synthetic route is as follows.Computed Properties of C6H7NO

General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, PdCl2(CH3CN)2 (0.05mol, 5mol%), Bi(OTf)3 (0.05mol, 5mol%), K2CO3 (1mmol) were added. Substrates 1 (1mmol) and MeOH (2mL) were added subsequently. The reaction tube was vacuumed and backfilled with oxygen (3 times). Then the reaction mixture was stirred at 60C for 3h in the presence of an oxygen balloon. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. Subsequently, the combined organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography with hexane/ethyl acetate to afford the corresponding products 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100-55-0, 3-Pyridinemethanol, and friends who are interested can also refer to it.

Reference:
Article; Hu, Yongke; Li, Bindong; Tetrahedron; vol. 73; 52; (2017); p. 7301 – 7307;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 141-86-6, 2,6-Diaminopyridine, 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, Application In Synthesis of 2,6-Diaminopyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2,6-Diaminopyridine

In a 100 mL three-necked round bottom flask, acetic anhydride (2.1 ml, 27.5 mmol) in 20 mL THF was added dropwise to a stirred mixture of pyridine-2,6-diamine (3.00 g, 27.5 mmol) and triethylamine (2.78 g, 27.5 mmol) in THF (40 ml) at 0C. After the reaction mixture was stirred at room temperature overnight, it was diluted with water (10 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with brine (2 x 1 OmL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with ethyl acetate/petroleum ether (10/i) to give the title compound as a solid. LCMS (ESI) calc?d for C7H9N30 [M+i ]: 152 found: 152; ?H NMR (300 MHz, CD3OD): oe7.38-7.32(m, 1H),718(d, J= 7.8 Hz, 1H), 6.24 (d,J= 8.1 Hz, 1H),2.08(s,3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,141-86-6, 2,6-Diaminopyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BENNETT, Frank; JIANG, Jinlong; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; SCOTT, Jack D.; TANG, Haiqun; ZHAO, Zhiqiang; HUANG, Yuhua; HUNTER, David; YANG, Dexi; ZHANG, Zhibo; FU, Jianmin; BAI, Yunfeng; ZHENG, Zhixiang; ZHANG, Xu; YOUNG, Katherine; XIAO, Li; (580 pag.)WO2016/206101; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 60290-21-3, 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. 60290-21-3, name is 4-Chloro-1H-pyrrolo[3,2-c]pyridine, molecular formula is C7H5ClN2, 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.

4-Chloro-1H-pyrrolo[3,2-c]pyridine (247 mg) synthesized by the method disclosed in was dissolved in DMF (7.0 ml). After cooling to 0C, N-iodosuccinimide (382 mg) was added thereto. The resulting mixture was stirred at room temperature for 1 hour, and then chloroform and water were added thereto to separate the organic layer. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a darkbrown solid (455 mg). Physical properties: m/z[M+H]+ 279.1

According to the analysis of related databases, 60290-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; SAGARA, Takeshi; ITO, Satoru; OTSUKI, Sachie; SOOTOME, Hiroshi; EP2657233; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 136117-73-2, Adding some certain compound to certain chemical reactions, such as: 136117-73-2, name is Imidazo[1,2-a]pyridine-7-carbaldehyde,molecular formula is C8H6N2O, 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 136117-73-2.

1.2(2) Preparation of Intermediate To a solution of intermediate of example 1.2(1). (27.369 mmol) in THF dry (120 ml) was added at 0 C. cyclopropylmagnesium bromide in THF 0.5 M (41.053 mmol) under nitrogen atmosphere. The reaction was stirred at 0 C. for 2 hours. Then the reaction mixture was concentrated to dryness. The residue was diluted with ethyl acetate (80 ml) and a aqueous solution of ammonium chloride (40 ml). An extraction was performed with brine (40 ml). The water layer was again extracted with EtOAc (80 ml). The organic layers were collected, dried over Na2SO4, filtered and concentrated to dryness, yielding 5.5 g of intermediate shown, used crude in the next step.

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. 136117-73-2, Imidazo[1,2-a]pyridine-7-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2012/35171; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 133081-24-0, 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 133081-24-0, name is 6-Hydrazinylnicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Preparation 47 6-(4-(4-cyano-2-methoxyphenyl)-5-hydroxy-lH-pyrazol-l- yl)nicotinic acid [0229] Combined ethyl 2-(4-cyano-2-methoxyphenyl)-3-(dimethylamino)acrylate (1.427 g, 5.20 mmol), 6-hydrazinylnicotinic acid (0.664 g, 4.34 mmol), and HCl (4.34 mL, 4.34 mmol) in 2-propanol (21.7 mL) and stirred at room temperature for 8 hours to give a solid. The solid was collected by filtration and combined with Hunig’s base (1.50 mL, 8.61 mmol) in 2- propanol (10 mL) and water (1 mL) and stirred for 32 hours at 50C, then 10 mL of 1 N HCl was added and the reaction was filtered to give a solid. The solid was washed with 30 mL MeOH and 30 mL of ether and dried in vacuo to give the title compound (708 mg, 73.3%) as a beige solid. MS m/z [M+H]+ 337.3.

According to the analysis of related databases, 133081-24-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; DAVIS, Melinda; IVETAC, Anthony; JONES, Benjamin; KIRYANOV, Andre, A.; KUEHLER, Jon; LANIER, Marion; MIURA, Joanne; MURPHY, Sean; WANG, Xiaolun; WO2014/160810; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 694-85-9, 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. 694-85-9, name is 1-Methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

To a stirred mixture of 1-METHYL-LH-PYRIDIN-2-ONE (33.47 g, 0.306 mol) and concentrated H2S04 (300 ML) at 100 °C was added concentrated HNO3 (120 mL) in portions. The reaction mixture was heated at this temperature overnight, and then poured into ice (1400 mL). The precipitate was filtered off and washed with water to give the title compound (Yield: 18.66 g, 30percent). LH NMR (400 MHZ, CDCl3) : 8 9.05 (d, 1H), 8.90 (d, 1H), 3.80 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,694-85-9, its application will become more common.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/69832; (2004); A2;,
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.16665-38-6, name is (4-Methoxypyridin-2-yl)methanol, molecular formula is C7H9NO2, molecular weight is 139.15, as common compound, the synthetic route is as follows.Quality Control of (4-Methoxypyridin-2-yl)methanol

(4) 2-Chloromethyl-4-methoxypyridine hydrochloride This was prepared by the method of Baker et. al., J. Chem. Soc., Chem. Comm., 3598, 1958, but starting with 2-hydroxymethyl-4-methoxypyridine (as prepared in (3) above, 44.05 g, 0.317 mole) and thionyl chloride (500 ml) to give the title compound as a reddish solid, 46 g (75%) which was used directly in the following preparation without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16665-38-6, (4-Methoxypyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; US4562197; (1985); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 115473-15-9, 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.115473-15-9, name is 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride, molecular formula is C7H10ClNOS, molecular weight is 191.68, as common compound, the synthetic route is as follows.

Example 3 (2S)-Methyl 2-(2-oxo-7,7a-dihydrothieno[3,2-c]pyridin-5(2H,4H,6H)-yl)-2-(2-chlorophenyl)-acetate (IV-1) [Show Image] 58.1 g (0.15 mol) of (R)-methyl 2-(2-chlorophenyl)-2-(4-nitrophenylsulfonyloxy)-acetate (II-1), 32.3 g (0.17 mol) of 5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride (III-1), and 37.8g (0.38 mol) of potassium bicarbonate were added to 500 ml of acetonitrile. The reaction was stirred under a nitrogen atmosphere at room temperature for 26 hrs. The reaction solution was allowed to stand and the insoluble material was filtered off, to obtain a dark red mother liquor. The solvent was evaporated under reduced pressure, and 35.4 g of an oil product was obtained after purification by flash column chromatography (petroleum ether:ethyl acetate = 4:1). Yield 70%. Recrystalization from ethanol afforded 18.1 g of a pure product (IV-1) as a white solid. mp: 146-148C, ee = 97.5%, [alpha]D19 = +114.0 (c 0.5, MeOH); 1H-NMR (300 MHz, CDCl3) delta 1.79-1.93 (m, 1 H), 2.30-2.40 (m, 1 H), 2.56-2.70 (m, 1 H), 3.00-3.27 (m, 2 H), 3.72 (s, 3 H), 3.79-3.93 (m, 1 H), 4.12-4.19 (m, 1 H), 4.89 (d, 1 H, J= 5.6 Hz), 6.00 (d, 1 H, J = 5.2 Hz), 7.26-7.50 (m, 4 H); 13C-NMR (75 MHz, CDCl3) delta 33.9, 34.0, 49.0, 49.7, 51.1, 51.6, 52.2, 52.4, 67.3, 76.6, 77.0, 77.4, 126.6, 126.8, 127.2, 129.8, 130.1, 132.7, 134.8, 167.2, 167.4, 170.8, 198.6; ESI-MS m/z 338.1 [M+H]+; HRMS Calcd for C16H17NO3SCl [M+H]+ m/z 338.0618, found 338.0626.

The chemical industry reduces the impact on the environment during synthesis 115473-15-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Jiangsu Vcare Pharmatech Co., Ltd; EP2532668; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6443-85-2, 2-(Pyridin-3-yl)acetonitrile, 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, 6443-85-2, blongs to pyridine-derivatives compound. Quality Control of 2-(Pyridin-3-yl)acetonitrile

b) 2-(3-pyridyl)ethylamine dihydrochloride was prepared as follows. A mixture of 1.3 g 3-pyridylacetonitrile, approximately 3 g Raney nickel and 30 ml methanol containing 10% ammonia by volume was hydrogenated at 35 psi for 20 hr using a Parr hydrogenator. The catalyst was filtered off over celite and the filtrate was evaporated. The residue was dissolved in methylene chloride, dried with magnesium sulfate, filtered and evaporated. The product was converted to the dihydrochloride using hydrogen chloride in dioxane. Crystallization from methanol/ether gave 1.4 g colorless crystals having a mp 145-148 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6443-85-2, its application will become more common.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US6759384; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 74784-70-6 ,Some common heterocyclic compound, 74784-70-6, molecular formula is C6H5F3N2, 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.

To a solution of l-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-iH-pyrazole-3- carboxylic acid (1.00 g, 2.65 mmol) in DCM (20 ml) was added 5 drops of DMF followed by 5 ml oxalyl chloride. The reaction mixture was stirred for one hour at room temperature, concentrated and the crude acid chloride redissolved in DCM (20 ml). DMAP (0.98 g, 8.03 mmol) was added followed by 5-(trifluoromethyl)pyridine-2-amine (0.49 g, 3 mmol). The reaction mixture was stirred at room temperature overnight then water was added and the product extracted with DCM (x2). The combined organic extracts were dried (Na2SO4), filtered and concentrated. Flash chromatography (heptane – heptane : EtOAc 90 : 10) gave 0.67 g (49%) of the title compound as a colorless solid.

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. 74784-70-6, 5-(Trifluoromethyl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/67443; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem