Month: April 2022

Related Products of 112006-57-2, 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. 112006-57-2, name is 2-(Benzylthio)-N,N-dimethylnicotinamide. A new synthetic method of this compound is introduced below.

EXAMPLE 2 N,N-Dimethyl-2-aminosulfonyl-3-pyridinecarboxamide A mixture of 4.4 ml of concentrated hydrochloric acid, 66 ml of methylene chloride, 34 ml of water and 4.0 g (14.7 mmol) of the N,N-dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide was cooled to 0 C. Maintaining a temperature of -5 to 3 C., 60 ml (40.5 mmol) of 5% sodium hypochlorite was added dropwise over 15 minutes. The resulting yellow emulsion was stirred at 0 C. an additional 20 minutes. The reaction mixture was then poured into water and extracted with methylene chloride. The combined organic extracts were kept at 0 C. and washed with a saturated sodium bisulfite solution and dried over sodium sulfate. After 30 minutes, the yellow solution was filtered into a reaction flask and cooled to -78 C. and 5 ml (431 mmol) of dry ammonia added. The reaction mixture was allowed to warm to room temperature and the solvent removed under reduced pressure. The resulting solid was slurried with 5 ml of water and the insoluble white solid collected by filtration to provide 2.0 g of the subject compound, m.p. 198-209 C.(d). NMR (DMSO): delta 2.70 (s, 3H, NCH3); 2.93 (s, 3H, NCH3); 7.60-7.75 (m, 1H); 7.90 (m, 1H); and 8.75 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112006-57-2, 2-(Benzylthio)-N,N-dimethylnicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4789393; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 18677-43-5, Adding some certain compound to certain chemical reactions, such as: 18677-43-5, name is 2,4-Dimethoxypyridine,molecular formula is C7H9NO2, 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 18677-43-5.

[1036] To a solution of compound 2 (28.7 g. 0.2 mol) in DMF (50 mL) was added NBS (35.5 g, 0.2 mol). The mixture was heated at 90 C. for 8 hours. The crude compound 3 was collected by filtration. (22 g, 50% 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. 18677-43-5, 2,4-Dimethoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Ramphal, Johnnie Y.; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/94456; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1796-84-5, 4-Ethoxy-3-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, SDS of cas: 1796-84-5, blongs to pyridine-derivatives compound. SDS of cas: 1796-84-5

Step 7: 3-[(4-(N-3-Nitropyrid-4-yl)aminomethyl)phenylsulfonyl]indole. A solution of 1-phenylsulfonyl-3-[(4-aminomethyl)phenylsulfonyl]indole (2.10 g, 4.79 mmol), prepared in step 6, and 4-ethoxy-3-nitropyridine (0.894 g, 5.31 mmol) in ethanol (20 mL) and triethylamine (1 mL) was heated at reflux for 70 hours. The reaction mixture was cooled to ambient temperature and diluted with ethyl acetate (250 mL). The organic phase was washed twice with H2 O and once with brine. The combined aqueous washings were extracted with ethyl acetate. The combined organic as layers were dried over Na2 SO4, filtered, and concentrated in vacuo. Chromatography on silica gel (ethyl acetate, then 0.2% ethanol/ethyl acetate) followed by recrystallization from ethyl acetate/ether gave 3-[(4-(N-3-nitropyrid-4-yl)aminomethyl)phenylsulfonyl]indole (350 mg, 23% yield). mp 97-102 C.

The synthetic route of 1796-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott Laboratories; US5486525; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 850663-54-6, 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 850663-54-6, name is 4-Chloro-5-nitropyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 34: 5-isopropoxy-lH-pyrrolo[2,3-c]pyridin-2(3H)-oneStep a: 4-chloro-2-isopropoxy-5-nitropyridine[0558] To a solution of 4-chloro-5-nitropyridin-2-ol (4.0 g, 23.0 mmol) in DMSO (25.0 mL)[0559] was added K2CO3 (6.35 g, 46.0 mmol) and the mixture was stirred at room temperature for 30 min. 2-iodopropane (5.87 g, 34.5 mmol) was added dropwise and the reaction mixture was stirred at 50C for 2 h. The mixture was poured into water and the resulting mixture was extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography to give 0.9 g of the title compound as an oil (18% yield).

According to the analysis of related databases, 850663-54-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZENOBIA THERAPEUTICS, INC.; BOUNAUD, Pierre-Yves; NIENABER, Vicki; STEENSMA, Ruo, W.; LOWE, John, A., III; WO2012/178015; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 106961-33-5, N,N-Dimethyl-1-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanamine, 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: 106961-33-5, blongs to pyridine-derivatives compound. Recommanded Product: 106961-33-5

Step (ii): Preparation of 6-methyl-2-(4-methylphenyl)imidazo[l,2-a|pyridine-3- acetonitrile (10)Dissolved the 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3-N,N- dimethylmethylamine (8) ( (230 grams, 0.82 mmol) (obtained from step (i)) in dichloromethane (600 mL) under stirring. Cooled the above solution to 0 – 5 0C, add ethylchloroformate (98.4 grams, 0.90 mmol) slowly over a period of 30 minutes. Stirred the above reaction mass for a period of 45 minutes at the same temperature, distilled off the solvent under reduced pressure, which produced 332 grams crude carbamate salt of dimethylaminomethyl imidazopyridine (2) as yellow colored solid. Dissolved the obtained solid immediately in water (690 mL), basify the solution to pH 7.5-8.0 using 10% sodium hydroxide solution. Added sodium cyanide (48.4 grams, 0.99 mmol) to the above reaction mass and stirred at 50 – 55 0C for a period of 3 hours. Cooled the above reaction mass to room temperature, extracted the solution with chloroform (300 mL, 2×200 mL). Combined organic layers and washed with water (500 mL) and brine (400 mL). Dried with anhydrous sodium sulfate, filtered and concentrated the solution until the volume reaches to 250 mL. Add methanol (1000 mL), stirred for the period of 30 minutes. Filtered the formed off white solid from the solution and dried in the oven until constant weight reached. Dry weight of obtained 6- methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3-acetonitrile(10) is 165.0 grams. Yield: 76% Purity: 96%Melting Range: 176.9 – 178.00C;IR spectra (cm”1): 2921, 2895, 2249, 1500, 1386, 1343, 824, 799;1H NMR (400 MHz, CDCl3): delta 2.42(s, 6H), 4.13 (s, 2H), 7.16 (dd, J= 9.1 Hz, J= 1.5 Hz, IH), 7.31 (d, J= 7.9 Hz, 2H), 7.58 (d, J= 8.0 Hz, 2H), 7.60 (d, J= 9.6 Hz, IH), 7.80(s, IH);Mass (m/z): 262.5 (M+H)+; Example 2:Preparation of 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3- acetic acid (12)Dissolved the 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine (9) (100 grams, 0.45 mmol) in acetic acid (500 mL) under stirring. Cooled the reaction mass to 5 – 10 0C, added 40% aqueous solution of dimethylamine (76 grams) slowly, followed by addition of paraformaldehyde (17.7 grams). Stirred the reaction mass at 50 – 55 0C for the period of 3 hours and removed acetic acid under reduced pressure. Added water (1000 mL), basify the solution (pH 8.0) by adding 30% sodium hydroxide solution. Extracted the solution with dichloromethane (3×300 mL), washed the organic layer with water (500 mL) and brine solution (500 mL). Dry with anhydrous sodium sulfate, filtered and distilled the solvent until the volume reaches to around 300 mL. This solution contains 6-methyl-2-(4-methylphenyl)imidazo[l ,2-a]pyridine-3-N,N- dimethylmethylamine (10), 89% purity by HPLC, and used further as it is. Cooled the above organic solution to 0 – 5 0C, added ethylchloroformate (58.3 grams, 0.54 mmol) slowly over a period of 30 minutes. Stirred the reaction mass for one hour at the same temperature, distilled off the solvent under reduced pressure to obtain carbamate salt as bright yellow colored solid (2). This solid was dissolved in water (300 mL), basified the solution to pH 7.5 – 8.0 using 10% sodium hydroxide solution. Added sodium cyanide (26.5 grams, 0.54 mmol) and stirred the reaction mass at 50 – 55 0C for a period of 3 hours. Cooled the reaction mass to room temperature and filtered the yellow solid and washed with water (500 mL). This crude solid contains 6- methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3-acetonitrile (10), 82% purity by HPLC, and used for hydrolysis without any further purification. The above crude solid was dissolved in 50% sulfuric acid (624 mL), refluxed the reaction mass at 110 0C for 4 hours. Cooled the reaction mass to room temperature and added to a flask contain of ice cold water (2.5 L). Basified the white ppt solution by adding sodium hydroxide flakes portion wise until pH 9.0. Extracted the solution with dichloromethane (2 x 300 mL) and discarded. Added carbon (5.0 grams), stirred for 30 minutes and filtered through a pad of celite. Acidified the solution pH 5.5 by adding glacial acetic acid and obtained white solid filtered. Filtered cake was washed with water (500 mL) and dried in the airflow oven at 60 – 65 0C until constant weight reached. 78.0 grams of 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3- aceticacid (12) obtained as off-white solid. Yield: 62.0% Purity: 99.5 %Melting Range: 234.0 – 235.20C; IR spectra (cm 1): 3427, 2919, 1701, 1508, 1183, 827, 805; 1H NMR (400 MHz, DMSO-c4): delta 2.31 (s, 3H), 2.34 (s, 3H), 4.08 (s, 2H), 7.17 (dd, J=9.1 Hz, J= 1.5 Hz, IH), 7.28 (d, J= 8.0 Hz, 2H), 7.51 (d, J= 9.1 Hz, IH), 7.61 (d, J= 8.0Hz, 2H), 8.22 (s, lH);Mass (m/z): 281.2 (M+H)+

The synthetic route of 106961-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; WO2009/7995; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 26163-03-1, 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. 26163-03-1, name is 3-Bromo-5-chloropyridin-2-amine, molecular formula is C5H4BrClN2, 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.

Example 39 2′-amino-6-(6-chloroimidazo[ 1 ,2-a]pyridin-8-yl)- 1 ‘,2,2-trimethylspiro[chroman-4,4′- imidazol]-5′(l’H)-oneStep A: 3-Bromo-5-chloro-2-pyridinamine (487 mg, 2.35 mmol) was diluted with ethanol (4 mL), followed by the addition of 2-chloroacetaldehyde (614 , 4.69 mmol). The reaction was heated at reflux for 3 hours. The reaction was cooled and loaded onto silica gel eluting with 10-50% ethyl acetate/hexanes to yield 8-bromo-6-chloroimidazo[l,2-a]pyridine (300 mg, 1.30 mmol, 55.2% yield).Step B: 2’-Amino-r,2,2-trimethyl-6-(4,4,5,5-tetramethyl

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 26163-03-1, 3-Bromo-5-chloropyridin-2-amine.

Reference:
Patent; ARRAY BIOPHARMA INC.; HUNT, Kevin, W.; RIZZI, James, P.; COOK, Adam; WO2011/72064; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1279815-46-1 ,Some common heterocyclic compound, 1279815-46-1, molecular formula is C9H7BrN2, 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 chilled (-78C) solution of l-(2-bromopyridin-4-yl)-cyclopropanecarbonitrile (1.16 g, 5.2 mmol) in toluene (30 mL) is added a 1 M solution of diisobutylaluminum hydride (DIBAH) (10.4 mL) in toluene. The mixture stirred at -78C for 1 hour and is then warmed to room temperature. After 1 hour, EtOAc (30 mL) is added, followed by 1 M aqueous solution of H2S04 (30 mL). The organic phase is separated and the aqueous layer is extracted with EtOAc (3 x 50 mL). The combined organic layers are dried over MgS04, filtered and concentrated to afford crude l-(2-bromopyridin-4-yl)- cyclopropanecarboxaldehyde which is used without purification. MS mJz 226.5, 228.5

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. 1279815-46-1, 1-(2-Bromopyridin-4-yl)cyclopropanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; KUZMICH, Daniel; WO2011/56440; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 10177-32-9, 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 10177-32-9 as follows.

MeI (0.2 mL, 3.00 mmol, 0.25 equiv) was added to a solution of methyl ester 14 (2 g, 12 mmol) in MeCN (16 mL), and the mixture was heated at 120 C under microwave conditions for 1 h. The solvent wasthen removed, and the oily residue was taken up in EtOAc, treated with charcoal, filtered, and re-concentrated to give 4-pyridinone 16 as a viscous oil that solidified to a near colourless solid on standing (2g, 95%). IR (ATR): 1645, 1717, 2950, 3013, 3053, 3094 cm-1. 1H NMR (CDCl3): delta = 8.12 (s, 1 H), 7.21-7.24 (dd, 3J = 7.7 Hz, 4J = 2.5 Hz,1 H), 6.44 (d, 3J = 7.5 Hz, 1 H), 3.83 (s, 3 H), 3.69 (s, 3 H). 13C NMR (CDCl3): delta = 174.8, 165.3, 146.6, 139.8, 122.7, 118.1, 51.9,44.9. HRMS (HESI): m/z [M + H]+ calcd for C8H9NO3: 168.0655; found:168.0657.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10177-32-9, its application will become more common.

Reference:
Article; Koperniku, Ana; Zamiri, Maryam; Grierson, David S.; Synthesis; vol. 51; 8; (2019); p. 1779 – 1790;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 127446-34-8, 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 127446-34-8, name is N-(6-Chloro-3-formylpyridin-2-yl)pivalamide. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 4-Benzyloxy-butan-l-ol (12) (8.43 mL, 48 mmol) in DMF (50 mL) was treated with NaH (1.52 g, 60 mmol) at O0C under nitrogen. The mixture was stirred at this temperature for 15 min, and then treated with N-(6-Chloro-3-formyl-pyridin-2-yl)-2,2- dimethyl-propionamide (11), (Journal of Organic Chemistry, 55(15), 4744-50; 1990, 5.76g, 24 mmol) in portions. After the addition was over, the mixture was left stirring for another 1 h. Aqueous NH4Cl was added to quench the reaction. The mixture was taken up into EtOAc and washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel to give the title compound (13) (6.15g) 1H-NMR (400 MHz, CDCl3): 11.50 (s, IH), 9.75 (s, IH), 7.80 (d, IH), 7.40 – 7.20 (m, 5H), 6.45 (d, IH), 4.50 (m, 4H), 3.50 (t, 2H), 2.00 – 1.70 (m, 4H), 1.40 (s, 9H).

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 127446-34-8, N-(6-Chloro-3-formylpyridin-2-yl)pivalamide.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/103559; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 867034-10-4, 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 867034-10-4, name is Ethyl 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Ethyl 7-chlo ro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (preparation described in Reference Example 1) (240 mg, 1.07 mmol), phenol (500 mg, 5.35 mmol) and cyclohexylamine (1.1 mL, 10.7 mmol) were combined in a sealed tube and heated at 100C for 6 h. The reaction tube was cooled to room temperature. The reaction mixture was diluted with ethyl acetate (10 mL), washed with 2 N sodium hydroxide (10 mL) and brine (10 mL), dried over magnesium sulfate, and evaporated to provide 538 mg of dark brown viscous oil. The viscous oil was purified by chromatography (Si02; 3: 1 hexanes/ethyl acetate) to give 7- chloro-N-cyclohexyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide as an off-white powder (218 mg, 0.785 mmol, 74%): ¹H NMR (300 MHz, CD30D) 81.20-1.55 (6H, m), 1.65-2.10 (4H, m), 3.90 (1H, m), 7.21 (lH, s), 7.61 (lH, d, J = 5.4 Hz), 7.93 (lH, d, J = 5.4 Hz) ; ESI MS m/z 278 [C14H16ClN3O + H](at).7-Chloro-N-cyclohexyl-1H-pyrrolo[2,3-c]pyridine-2- carboxamide (230 mg, 0.828 mmol), triethylamine (0.25 mL) and palladium (II) chloride (3 mg, 2 mol%) were combined in N,N- dimethylformamide (5 mL) under an atmosphere of hydrogen. The (at)’l’i£c£i(at)d£”‘”‘£tI%8(at)tlr(at)”(at)(at)(at)lk9″”(at)(at)ti(at)lated at 60C for 3 h. The reaction mixture was cooled to room temperature and the catalyst was removed by filtration through a pad of diatomaceous earth and washed with ethyl acetate. Evaporation of the solvents provided crude product (169 mg, 84%) as an off-white solid. Purification by chromatography (Si02; 0-10% methanol in methylene chloride, 1400 mL) afforded N-cyclohexyl-1H- pyrrolo [2,3-c]pyridine-2-carboxamide (101 mg, 0.414 mmol, 50%) as fine, white needles: mp 298-301C, ¹H NMR (300 MHz, CD30D) 8 1.20-1.55 (6H, m), 1.65-2.10 (4H, m), 3.90 (lH, m), 7.21 (1H, s), 7.15 (1H, s), 7.65 (lH, d, J = 5.7 Hz), ‘8.09 (lH, d, J = 5.7 Hz), 8.77 (lH, s) ; ESI MS m/z 244 [C14H17N3O + H] +; HPLC (Method A) >99% (AUC), tR = 13.2 min.

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 867034-10-4, Ethyl 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/97129; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem