Tag: M.W:100-200

Reference of 490-11-9, 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. 490-11-9, name is Pyridine-3,4-dicarboxylicacid, molecular formula is C7H5NO4, 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.

10265] WXO18-1 (40.00 g, 239.35 mmol, 1.00 eq) was dissolved in anhydrous methanol (1.00 L), then concentrated sulfuric acid (11.98 g, 119.67 mmol, 6.51 mE, 98% purity, 0.50 eq) was added at 85 C. The mixture was stirred under nitrogen condition for 40 h. After reaction, the reaction liquid was concentrated under vacuum, then the concentrated solution was slowly added to saturated sodium bicarbonate solution (1,500 mE). The resulting mixture was stirred until there was no bubble generated, and extracted with ethyl acetate (1,000 mLx3). The organic phase was washed with saturated sodium chloride solution (800 mLx3), dried with anhydrous sodium sulfate and filtered. The filtrate was dried by rotary evaporation to obtain the brown oily compound WXO18-2. ?H NMR (400 MHz, CDC13) oe ppm: 9.06 (s, 1H), 8.82 (d, J4.90 Hz, 1H), 7.49 (d, J5.02 Hz, 1H), 3.94 (m, 6H).

According to the analysis of related databases, 490-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHENZHEN SALUBRIS PHARM CO LTD.; Wu, Chengde; Yan, Jie; Xu, Wenjie; Yu, Tao; Li, Ning; Chen, Shuhui; US2018/305346; (2018); 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.83766-88-5, name is 2-(tert-Butoxy)pyridine, molecular formula is C9H13NO, molecular weight is 151.21, as common compound, the synthetic route is as follows.Product Details of 83766-88-5

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83766-88-5, 2-(tert-Butoxy)pyridine, and friends who are interested can also refer to it.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 98139-15-2, Adding some certain compound to certain chemical reactions, such as: 98139-15-2, name is 4-Aminopicolinonitrile,molecular formula is C6H5N3, 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 98139-15-2.

Into a 30-mL sealed tube, was placed 2-bromo-5-methoxy-4-[3-(pyrrolidin-l- yl)propoxy]pyridine (314 mg, 1.00 mmol, 1.00 equiv.), 4-aminopyridine-2-carbonitrile (240 mg, 2.01 mmol, 2.00 equiv.), Pd2(dba)3-chloroform (0.1 g, 0.10 equiv.), t-BuXPhos (0.085 g, 0.20 equiv.), Cs2C03 (970 mg, 2.97 mmol, 3.00 equiv.), dioxane (10 mL). The resulting solution was stirred for 16 h at 110 C in an oil bath. The reaction was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×30 mL of ethyl acetate and the organic layers combined. The organic layer was washed with 1×50 mL of brine, dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The crude product (3 mL) was purified by Flash- Prep-HPLC with the following conditions (CombiFlash-1): Column, C18 silica gel; mobile phase, MeCN_Water=l :5 increasing to MeCN_Water=10: l within 120 min; Detector, UV 254 nm. 70 mg product was obtained. This resulted in 70 mg (20%) of 4-([5-methoxy-4-[3- (pyrrolidin-l-yl)propoxy]pyridin-2-yl]amino)pyridine-2-carbonitrile as an off-white solid.

According to the analysis of related databases, 98139-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 6960-22-1, name is 6-Methylnicotinamide. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-Methylnicotinamide

Example 4: Synthesis of 106Step 1 :3.00 g (22.0 mmol) 6-methylnicotinamide is dissolved in 10 ml THF under argon-atmosphere and 34 ml (34 mmol; 1.5 eq.) 1 M lithium aluminum hydride in THF are added. After 45 min additional lithium aluminum hydride (1.22 g; 1.5 eq.) in 40 ml THF is added. The reaction mixture is heated to 60C for 24 h under stirring. The reaction mixture is carefully quenched under stirring with isopropyl alcohol, methanol and finally water at 0C. The solvent is removed under vacuum. After addition of 100 ml 2N NaOH solution and 100 ml DCM the white precipitate is centrifuged off and the aqueous layer is extracted 4 times with 60 ml DCM. The combined organic layers are dried over magnesium sulphate and the solvent is removed under reduced pressure yielding 1.57 g (12.9 mmol; 58%) of the amine 2 which is used without further purification for subsequent reaction steps.

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, 6960-22-1, 6-Methylnicotinamide.

Reference:
Patent; JERINI AG; WO2006/128670; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1132-37-2 , The common heterocyclic compound, 1132-37-2, name is Dipyridin-2-ylmethane, molecular formula is C11H10N2, 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.

[0158] Benzyl potassium 4.0 g (30.5 mmol) was added into a solution of dipyridin-2-ylmethane 5.2 g (30.5 mmol) in 100 mL THF at -70 C. over 10 minutes. The mixture was stirred at ambient temperature for 16 hours after which the bright yellow mixture was filtrated and washed with THF. Solvents were evaporated and the product washed with pentane and evaporated to yield a bright yellow solid which on the basis of the 1H-NMR spectrum in DMSO-d6 was [DPM-K+] [THF]0.5. Yield 5.44 g (73.0%) based the THF complex (Mw=244.35 g mol-1). The product decomposed during ETMS analysis. Elemental analysis calculated for [DPM-K+] [THF]0.5: C 64.6%, H 4.8%, N 12.0%, K 21.9%. Found: C 63.9%, H 5.36%, N 11.46%, K 16.0%. NMR spectra were recorded at +22.7 C., +50 C. and at +70 C. in DMSO-d6. The complex shows fluxional behaviour in NMR with increasing temperature which is caused by the transition between the two resonance structures A and B. The peaks coalescence at +70 C. The singlet bridgehead proton is exchanged slowly with the methyl deuterium of DMSO-d6 which is seen as an appearing triplet in 13C-NMR. 1H-NMR in DMSO-d6 at +70 C. delta: 8.20 and 6.25 (broad coalesence peaks, 2H, from HaHa’), 7.65 (d, 2H, from HdHd’), 6.78 (broad, 2H, from HbHb’), 5.76 (broad, 2H, from HcHc’), 4.62 (S, 1H, exchangeable proton He). 13C-NMR in DMSO-d6 at delta: 160.2, 147.9, 147.8, 132.3, 131.2, 116.9, 114,3, 105.3, 103.3, triplet 87.2 from exchanged CHeDMSO-d6. 13C-CPMAS delta: 163, 150, 138, 119, 109, 82.

The synthetic route of 1132-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Andell, Ove; Maaranen, Janne; Hoikka, Jouni; Vanne, Tiina; Rautio, Soile; US2003/225275; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 697739-12-1, Ethyl imidazo[1,5-a]pyridine-8-carboxylate, 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: 697739-12-1, blongs to pyridine-derivatives compound. Recommanded Product: 697739-12-1

Description 36 (8.67 g, 45.6 mmol) and KOH [1. OM in methanol] (91.2 ml, 91.2 mmol) were mixed together and heated to reflux for 30 minutes when HPLC indicated the reaction was complete. The mixture was cooled and evaporated to dryness. Water (50 ml) was then added, and the mixture acidified with 2N HC1 to give a yellow precipitate. The precipitate was filtered and washed successively with water, ethanol, and diethyl ether to give the title compound (3.1 g, 42%) as a yellow solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,697739-12-1, Ethyl imidazo[1,5-a]pyridine-8-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Merck Sharp & Dohme Limited; WO2004/46133; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 60781-83-1, 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. 60781-83-1, name is 4-Phenylpyridin-2-amine. A new synthetic method of this compound is introduced below.

EXAMPLE 8 2,3-Dihydro-6-phenylcyclopenta[d]pyrido[1,2-a]pyrimidin-10(1H)-one A mixture of 17.0 g. of 2-amino-4-phenylpyridine and 31.2 g. of ethyl cyclopentane-2-carboxylate is heated at an internal temperature of 160-165 for 4 hours. During this time ethanol distils from the reaction mixture and is collected in a Dean-Stark trap. During the 4 hours of heating, about 5.5 ml of distillate is collected. When the reaction mixture is allowed to cool, a crystalline solid separates. The mixture is cooled to 0 and the solid filtered. Recrystallization from cyclohexane gives 24.7 g. of 2,3-dihydro-6-phenylcyclopenta[d]pyrido[1,2-a]pyrimidin-10(1H)-one.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60781-83-1, its application will become more common.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US3965100; (1976); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 88912-24-7 ,Some common heterocyclic compound, 88912-24-7, molecular formula is C6H3Cl2NO2, 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.

EXAMPLE 12 2,3-bis(methylthio)pyridine In a 4-necked flask equipped with a Dry Ice condenser, mechanical stirrer, thermometer and dropping funnel, 172.2 g of t-BuOK was dissolved in 200 ml of DMSO at room temperature with stirring under N2. The solution was cooled with an ice bath while 50.0 g of methanethiol was added. The mixture was stirred for 30 minutes, then the ice bath was removed. A solution of 5,6-dichloro-2-pyridinecarboxylic acid (90.6 g) in 250 ml of DMSO was added at a rate such that the exotherm did not cause the temperature of the mixture to exceed 75 C. A dense slurry formed. An additional 500 ml of DMSO was added, and the slurry was stirred for 42 hours at 60 C. After cooling to room temperature, 500 ml of water was added to the reaction mixture, which was then added to 3.5 liters of ice water, and acidified to pH 1 with concentrated HCl. The yellow precipitate which formed was collected and dried which gave 87.33 g of a mixture of 5-chloro-6-(methylthio)-2-pyridinecarboxylic acid (~3.36 g) and 5,6-bis(methylthio)-2-pyridinecarboxylic acid (~83.97 g). The relative amounts of the 5-chloro-6-(methylthio)-2-pyridinecarboxylic acid and 5,6-bis(methylthio)-2-pyridinecarboxylic acid were estimated based on the amounts of the mono and bis-adducts isolated after decarboxylation.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,88912-24-7, its application will become more common.

Reference:
Patent; The Dow Chemical Company; US4616087; (1986); A;,
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. 588720-29-0, name is Imidazo[1,5-a]pyridine-7-carboxylic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 588720-29-0

To a 50 mL single neck RB flask starting 1H-Imidazol (1,5-a)pyridine-7-carboxylic acid (0.5 g, 3.086 mmol) was added, followed by ethyl ester of L-Leucine Hydrochloride (0.5 g, 3.086 mmol), HATU (0.323 g, 0.85 mmol) and DMF (8 mL). The contents were stirred for 5 mins. After clear solution formation DIPEA (1.1 mL, 6.172 mmol) was added and the reaction mass stirred for 16h at 20-30C. After 16h, the completion of the reaction was confirmed byTLC/LCMS, and worked-up. Ice-cold water (2OmL) was added slowly to the reaction mixture with stirring. The product was extracted with ethyl acetate (2x2OmL). The ethyl acetate extracts were separated washed with (1×20 mL) water, separated the organics, dried over anhydrous sodium sulphate and distilled off the volatiles under reduced pressure to get the crude product. This crude material was subjected to purification using preparative RP HPLC. The pure material thus obtained yielded 60-70% yield of the product of desired purity.

The synthetic route of 588720-29-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALKEM LABORATORIES LTD.; NAGARAJ, Harish Kumar Mysore; BANDODKAR, Balachandra S; RAVILLA, Lokesh; YELLAPU, Sudhakar; RUDRESHA, Ashok Seegebagi; SINGH, Jitendra Kumar; G, Vaidyanathan.; (95 pag.)WO2016/27285; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131747-55-2 ,Some common heterocyclic compound, 131747-55-2, molecular formula is C6H6FNO, 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.

Di-tert-butyl azodicarboxylate (0.36 g, 1.57 mmol) was added to a suspension of (2-fluoropyridin-3-yl)methanol (10, 0.20 g, 1.57 mmol), N-(4-(2,4-difluorophenoxy)phenyl)-N-ethylsulfonylamine (0.49 g, 1.56 mmol) and polystyrene resin-bound triphenylphosphine (0.52 g, 1.57 mmol, 3 mmol/g) in anhydrous tetrahydrofuran (5 mL) at 0 C. under nitrogen. The resulting yellow suspension was warmed to room temperature and stirred for 19 h, after which additional polystyrene resin bound triphenylphosphine (0.52 g, 1.57 mmol, 3 mmol/g) and di-tert-butyl azodicarboxylate (0.36 g, 1.57 mmol) were added. This solution was stirred for 24 h after which the suspension was diluted with anhydrous tetrahydrofuran (100 mL) and the solids were removed by vacuum filtration. The filtrate solvent was removed under reduced pressure to provide the crude product as a yellow oil. This oil was purified by medium pressure liquid chromatography on silica gel, eluting with hexanes/ethyl acetate (7:3), to provide a colorless oil. This oil was triturated with hexanes/ethyl acetate (4-5 mL) to give the title compound as a white powder (0.28 g, 53%): mp 110-112 C.; TLC Rf (3:2 hexanes/ethyl acetate)=0.44; 1H NMR (300 MHz) 8.11 (m, 1H), 7.90 (m, 1H), 7.24-7.15 (m, 3H), 7.11-7.03 (m, 1H), 6.98-6.86 (m, 2H), 6.84 (d, J=6.8 Hz, 2H), 4.91 (s, 2H), 3.15-3.07 (q, J=7.4 Hz, 2H), 1.43 (t, J 5=7.4 Hz, 1H) ppm; 13C NMR (75 MHz) 163.3, 161.3, 160.1, 157.8, 156.5, 153.1, 147.5 (d, J=14.9 Hz), 141.7, 139.1, 133.6, 130.5, 123.8 (d, J=9.7 Hz), 122.1, 119.1 (d, J=29.2 Hz), 117.5, 112.0 (d, J=22.9 Hz), 106.0 (t, J=24.3 Hz), 49.1, 46.0, 8.44 ppm; APCI MS m/z 423 [C20H17F3N2O3S+H]+. Anal. Calcd. for C20H17F3N2O3S: C, 56.87; H, 4.06; N, 6.63. Found: C, 56.90; H, 4.10; N, 6.45.

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. 131747-55-2, 2-Fluoro-3-(hydroxymethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Coleman, Darrell Stephen; Jagdmann, Gunnar Erik; Johnson, Kirk Willis; Johnson, Michael Parvin; Large, Thomas Hallett; Monn, James Allen; Schoepp, Darryle Darwin; Barda, David Anthony; Britton, Thomas Charles; Dressman, Bruce Anthony; Henry, Steven Scott; Hornback, William Joseph; Tizzano, Joseph Patrick; Fichtner, Michael William; US2004/6114; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem