Tag: M.W:100-200

Application of 98027-36-2, 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 98027-36-2, name is 3-Amino-5-chloro-2-hydroxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

The substrate 3-amino-5-chloro-2-hydroxypyridine (464 mg, 3.21 mmol))And methyl 4-aldehyde-2-methoxybenzoate (623 mg, 3.21 mmol)Dissolved in 10mL of methanol,1 ml of acetic acid and sodium cyanoborohydride (403 mg, 6.42 mmol) were added to the reaction mixture.The reaction was refluxed overnight. Quenched with water, spun off methanol, extracted with ethyl acetate, and combined.Drying, purification by methylene chloride / methanol = 30/1 to afford compound 40A (398 g, 38% yield).

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 98027-36-2, 3-Amino-5-chloro-2-hydroxypyridine.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Chen Huanming; Liang Bo; Cao Wenjie; Zhang Guiping; Zhao Zhongqiang; Jiang Zhaojian; Zuo Gaolei; Xu Wanmei; Gong Hongju; Zhang Peng; Wang Jianghuai; Li Qingsong; Gao Chunhua; (79 pag.)CN104045552; (2019); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 71777-70-3, 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.71777-70-3, name is Ethyl 4-ethoxypicolinate, molecular formula is C10H13NO3, molecular weight is 195.22, as common compound, the synthetic route is as follows.

To a solution of ethyl 4-ethoxypicolinate 198 (1 .6 g, 8.2 mmol) in concentrated H2SO4 (80 mL) was added NBS (2.7 g, 14.8 mmol). The reaction was stirred at room temperature overnight then quenched by addition of saturated aqueous NaHCCb (150 mL). The aqueous layer was extracted with DCM (3 x 130 mL) and the combined organic layers dried ( a2S04) and concentrated to give the title compound as a yellow solid (2.0 g, 91 %). 1H NMR (400 MHz, CDCI3) delta 8.67 (s, 1 H), 7.63 (s, 1 H), 4.94-4.40 (m, 2H), 4.29-4.23 (m, 2H), 1 .54-1 .51 (0853) (m, 3H), 1 .46-1 .42 (m, 3H); LCMS-C: RT 2.59 min; m/z 274.0, 276.0 [M+H]+

Statistics shows that 71777-70-3 is playing an increasingly important role. we look forward to future research findings about Ethyl 4-ethoxypicolinate.

Reference:
Patent; CTXT PTY LTD; BERGMAN, Ylva Elisabet; FOITZIK, Richard Charles; MORROW, Benjamin Joseph; CAMERINO, Michelle Ang; WALKER, Scott Raymond; LAGIAKOS, H. Rachel; FEUTRILL, John; STEVENSON, Graeme Irvine; STUPPLE, Paul Anthony; (222 pag.)WO2016/34673; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59782-90-0, 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 59782-90-0 as follows.

Under the protection of nitrogen, into the three-necked flask, add 53g benzylamine. Then use ice-bath to cool to 3 C. Then continue to add dropwise n-propanal 28g. Control dropwise addition time to 1h. Then add dropwise in batches 13g mass concentration of 10% KOH. Add dropwise 3 time. Then allow the layers to separate. To the organic phase, add 5g mass concentration of 10% KOH. Allow to stand overnight to prepare N-propylidenebenzylamine; Into a 250 ml four-necked flask, add 68g of the above-mentioned prepared N-propylidenebenzylamine. Then add 105 ml dichloromethane and triethylamine 47g. Stir and cool to 0 C, Then continue adding dropwise chloroacetyl chloride 57g. Control the dropwise addition at 1h. Then elevate temperature to 20 C. Continue reacting for 10 min; After the reaction is finished, the deionized water washing and the mass fraction of 10% hydrochloric acid pickling and the mass concentration is 10% of sodium hydroxide caustic wash, finally by reduced pressure distillation to remove the solvent, the reaction liquid prepared, subsequently heating the reaction liquid to column chromatography separation, collection acyl compound; In a 250 ml three-necked flask, add 23g dimethylformamide and 100 ml of 1,2-dichloromethane. Then stir and cool to 0 C. Then take 5.8g triphosgene. Use 50 ml of 1,2-dichloroethane to dissolve. Then add dropwise to the three-necked flask. Control the dropwise addition at 1h. After the completion of the dropwise addition, continue adding dropwise 4.4g of above-mentioned prepared acyl compound. Heat to 55 C and stir reaction for 1h; After the completion of reaction, washing with a large amount of deionized water and collecting the organic phase, for mass fraction of 10% sodium hydroxide solution to adjust the pH to 8.0, subsequently to its hierarchical collection of the organic layer, the solvent is removed by reduced pressure distillation column chromatography separation thereof, to collect colorless transparent crystal 2,3-dichloro-5-methylpyridine; 123.1g of nicotinic acid and 10 ml of 2,3-dichloro-5-methylpyridine were stirred and mixed; Elevate temperature to 55 C. Then add 270g phosphorus trichloride. At 70 C, enter chlorine gas for 2h. Continue heating to 150 C. Then 600 ml ethyl acetate and 20g sodium carbonate were added to the above-mentioned solution. Then continue reaction for 2h. Dry and concentrate and then dissolve in 100 ml toluene. Heat to 80 C and slowly enter phosgene. After reacting for 2h, the sodium carbonate is used to adjust the pH to 7.0, and separating an organic layer to dry the same, subsequently prepared desolution of the 2,3-chloro-5-chloromethyl pyridine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59782-90-0, its application will become more common.

Reference:
Patent; Changzhou University; Chen, Xingquan; (6 pag.)(2016);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 51454-63-8, 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.51454-63-8, name is 2-(Hydroxymethyl)isonicotinonitrile, molecular formula is C7H6N2O, molecular weight is 134.14, as common compound, the synthetic route is as follows.

To a cooled solution of oxalyl chloride (13.2mL, 150mmol) in anhydrous DCM (86mL) under nitrogen atmosphere at -78C was added DMSO (21.2ml_ dropwise over 20 minutes. The mixture was stirred for 15 minutes at (-78C) before 2-hydroxymethyl-isonicotinonitrile (4.0g, 30 mmol) dissolved in anhydrous DCM (60mL) was added dropwise to the reaction mixture over 5 minutes. The reaction was stirred for 2 hrs at -78C maintaining a nitrogen atmosphere. A white solid precipitate formed and the temperature was raised to (-55C) and triethylamine (6.15mL, 450mmol) was added dropwise for over 15 minutes, cooling bath was removed allowing the mixture to warm to room temperature over 2 hrs. The mixture was diluted with DCM (400ml_) and washed with brine (2x 50mL). The aqueous phase was extracted with DCM (3x 50 ml_). The combined organic layers were combined and concentrated in vacuo. A buff white solid was isolated that was used without any further purification. Single peak in LC-MS analysis, (yield taken to be quantitative), m/z (LC-MS, ESP), RT=2.53mins, (M+H)=133.0.

Statistics shows that 51454-63-8 is playing an increasingly important role. we look forward to future research findings about 2-(Hydroxymethyl)isonicotinonitrile.

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2006/21801; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 135124-71-9, 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.135124-71-9, name is 5-(Hydroxymethyl)nicotinonitrile, molecular formula is C7H6N2O, molecular weight is 134.14, as common compound, the synthetic route is as follows.

To a stirred solution of 5-(hydroxymethyl)nicotinonitrile (3 g, 0.022 mol) in DCM (30 mL), 4M HC1 in l,4-dioxane (5 mL) was added and concentrated the mixture under vacuum. To the resulting residue, thionyl chloride (20 mL) was added and stirred the mixture at 60 C for 3h. After completion, the reaction was cooled to room temperature and diluted with toluene (150 mL) and filtered off the solid that precipitated out. The filtrate was diluted with DCM (200 mL) and washed with saturated sodium bicarbonate solution (200 mL). The organic layer was dried over sodium sulphate and concentrated to obtain 5-(chloromethyl)nicotinonitrile (Yield: 1.2 g, 35%) as yellow solid. 1H NMR (400 MHz, DMSO-d6, ppm): d 4.86 (s, 2H), 8.42 (s, 1H), 8.94 (d, / = 2.0 Hz, 1H), 8.99 (d, J = 2.0 Hz, 1H). Scheme -9: Synthesis of 3-(hydroxymethyl)-[l,l’-biphenyl]-2-carbonitrile

Statistics shows that 135124-71-9 is playing an increasingly important role. we look forward to future research findings about 5-(Hydroxymethyl)nicotinonitrile.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; D A, Jeyaraj; PENDYALA, Muralidhar; SIVANANDHAN, Dhanalakshmi; RAJAGOPAL, Sridharan; (233 pag.)WO2019/175897; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 98197-88-7, 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 98197-88-7 as follows.

A 50-mL round-bottom flask was charged with (4-nitropyridin~2-yl)mefhano (1.07 g, 6 94 mmol), propargyl alcohol (5 mL), and the sodium alkoxide of propargyi alcohol (2.22 g, 28.44 mmol, 4.1 equiv, prepared from propargyiic alcohol and NaH). A reflux condenser was attached, and after the reaction mixture was heated to reflux for 2 h, the reaction mixture was cooled to 23 C, quenched with saturated aqueous NF C (5 mL), and extracted with CH2G2 (3 x 10 mL) using a separatory funnel. The combine organic layers were dried over anhydrous Na2504, filtered, and concentrated in vacuo to deliver (4- (prop-2~yn-1~yoxy)pyridin-2~yl)methanol (830 mg, 73% yield). The crude materia was used directly in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98197-88-7, its application will become more common.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; KOIDE, Kazunori; BEIN, Kiflai; BRESSIN, Robert, Kruger; BURROWS, James, Proviano; GAMBINO, Adriana; LEIKAUF, George, D.; PHAM, Dianne; (80 pag.)WO2020/27905; (2020); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 51285-26-8 ,Some common heterocyclic compound, 51285-26-8, molecular formula is C6H8ClN3, 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.

A mixture of 157.8 g. (1.0 mol) of 2-pyridinecarboxamidine hydrochloride 23, 54.2 g (1.0 mol) of sodium methoxide in 400 ml of dry methanol was stirred for 30 minutes. The sodium chloride was filtered and the filtrate was concentrated to dryness. The residue and 83 g (1.0 mole) of 3-methoxyacrylonitrile 24 were heated (100-160°) together for 3 hours, at this point the evolution of ethanol had stopped and the melt had started to crystallize. The product 25 was cooled to room temperature, suspended in methanol, filtered and dried to obtain 25 125.6 g, (73percent yield).

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. 51285-26-8, Picolinimidamide hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHY THERAPEUTICS LLC; HADARI, Yaron R.; CARTA, Luca; SCHMERTZLER, Michael; WILLIAMS, Theresa M.; REYNOLDS, Charles H.; HUTCHESON, Rebecca; (1452 pag.)WO2018/237084; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 92992-85-3, 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 92992-85-3, name is 2-Bromo-3,5-dimethylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Compound 11b was prepared from 2-bromo-3,5-dimethylpyridine (9b) and 10 in a manner similar to that described for compound 11a, with a yield of 68% as a brown syrup. 1H NMR(DMSO-d6) d 2.29 (s, 3H), 2.30 (s, 3H), 4.55 (d, 2H, J = 5.7 Hz),5.21 (t, 1H, J = 5.7 Hz), 7.38 (d, 2H, J = 8.3 Hz), 7.47 (d, 2H,J = 8.3 Hz), 7.52 (br s, 1H), 8.30 (br s, 1H); MS (ESI) m/z 214 [M+H]+.

According to the analysis of related databases, 92992-85-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hamaguchi, Wataru; Masuda, Naoyuki; Miyamoto, Satoshi; Kikuchi, Shigetoshi; Narazaki, Fumie; Shiina, Yasuhiro; Seo, Ryushi; Amano, Yasushi; Mihara, Takuma; Moriguchi, Hiroyuki; Hattori, Kouji; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3351 – 3367;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 135450-23-6 ,Some common heterocyclic compound, 135450-23-6, molecular formula is C7H5ClN2, 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.

General procedure: 4-((5-(2-aminopyridin-3-yl)isoxazol-3-yl)methyl)phenol (Intermediate C, 80mg, 0.30mmol) was dissolved in DMF (lmL) and potassium 2-methylpropane-2-olate (1M in THF, 0.33mL, 0.33mmol) was added dropwise. The mixture was stirred for 5min and a solution of 3-(bromomethyl)-5-methylisoxazole (63.2mg, 0.36mmol) in DMF (0.5mL) was added. The resulting mixture was stirred for 30min and directly purified by column chromatography (Si02, hexane/ethyl acetate). Fraction containing the product were concentrated under reduced pressure and further purified by reversed phase flash chromatography (C18, acetonitrile/water) to yield 3-(3-(4-((lH-pyrazol-l-yl)methyl)benzyl)isoxazol-5-yl)pyridin-2-amine (7lmg, 0.20mmol, 66%) as a white solid. 400 MHz l NMR (CDCl3) d 8.13 (s, 1H), 7.70 (dd , J= 7.7, 1.8 Hz, 1H), 7.24 – 7.16 (m, 2H), 6.98 – 6.89 (m, 2H), 6.70 (dd, J= 7.7, 4.8 Hz, 1H), 6.23 (s, 1H), 6.10 (d, J= 1.1 Hz, 1H), 5.44 (s, 2H), 5.09 (s, 2H), 3.99 (s, 2H), 2.42 (d, .7= 0.9 Hz, 3H). MS: 363.3 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135450-23-6, its application will become more common.

Reference:
Patent; AMPLYX PHARMACEUTICALS, INC.; TRZOSS, Michael; COVEL, Jonathan; SHAW, Karen Joy; WEBB, Peter; (240 pag.)WO2019/113542; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 112110-07-3, 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

To degassed dioxane (10mL) were added sequentially 5- trifluoromethylpyridin-3-amine (2) (309mg, 1.9mmol), 2-chloropyrazine (1) (0.26mL, 2.86mmol), Pd2(dba)3 (52mg, 0.06mmol), XantPhos (66mg, 0.1 1 mmol) and Cs2C03 (1.24g, 3.8mmol) with continued degassing. The reaction mixture was heated up to 90C overnight. An additional portion of 2-chloropyrazine (0.17ml_, 1.91 mmol) was then added and the reaction mixture was heated up to (0304) 90C overnight. Once cooled down to rt, it was poured into H20 (20ml_) and extracted with EtOAc (3 x 20ml_). The combined organic extracts were dried over MgS04, filtered and concentrated in vacuo. Purification by silica gel column chromatography with hexane/EtOAc (1 :0-1 :2) gave a residue which was re- dissolved in CH2CI2/MeOH (4:1 , 50ml_) and swirled with MP-TMT resin (440mg, 1.3mmol/g) at rt overnight. The solution was filtered, the resin washed with CH2CI2/MeOH (4:1 , 100ml_) and the filtrate concentrated in vacuo to yield (3) as a yellow solid (202mg, 44%). (0305) LCMS (ES): Found 241.0 [M+Hf. (0306) 1H NMR (300 MHz, DMSO-cf6), d: 10.14 (s, 1 H), 9.00 (d, J=2.4 Hz, 1 H), 8.69 (t, J= 2.0 Hz, 1 H), 8.52 (d, J=0.9 Hz, 1 H), 8.32 (d, J=1.5 Hz, 1 H), 8.25 (dd, J= 2.8, 1.5 Hz, 1 H), 8.08 (d, J= 2.8 Hz, 1 H). (0307) 19F NMR (282 MHz, DMSO-cf6), d: -61.09 (s, 3F).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem