Day: September 28, 2021

Electric Literature of 1462-86-8, Adding some certain compound to certain chemical reactions, such as: 1462-86-8, name is 3-Aminopicolinic acid,molecular formula is C6H6N2O2, 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 1462-86-8.

General procedure: In a vial, 0.088 mmol (1.2 equiv) of the 3-aminopicolinic acid were added and dissolved in 0.5 mL mixture of DCM:DIEA (9:1), then 41 mg (0.110 mmol, 1.5 equiv) of HATU were added. The mixture was stirred for 10 min, and 20 mg (0.073 mmol, 1.0 equiv) N-(4-aminophenyl)phthalimide dissolved in 0.5 mL of DCM:DIEA (9:1), followed by 3 drops of DMF. The reaction was stirred for 24 h at room temperature. After this time, the reaction was quenched with the addition of water, and was worked up by extraction with DCM (2 mL, thrice). The organic phased was filtered through a phase separator, volatiles were evaporated, the crude was dissolved in DMSO and purified by preparative HPLC.

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. 1462-86-8, 3-Aminopicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gogliotti, Rocco D.; Engers, Darren W.; Garcia-Barrantes, Pedro M.; Panarese, Joseph D.; Gentry, Patrick R.; Blobaum, Anna L.; Morrison, Ryan D.; Daniels, J. Scott; Thompson, Analisa D.; Jones, Carrie K.; Conn, P. Jeffrey; Niswender, Colleen M.; Lindsley, Craig W.; Hopkins, Corey R.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 12; (2016); p. 2915 – 2919;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6602-32-0 , The common heterocyclic compound, 6602-32-0, name is 2-Bromo-3-hydroxypyridine, molecular formula is C5H4BrNO, 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 stirred solution of 2-bromo-3-hydroxypyridine (50 g, 287.356 mmol) in THF at 0 C was added i-BuO-K (51.49 g, 459.7 mmol) portion wise. After stirring the reaction mixture for 15 mins, methoxymethyl chloride (34.473 mL, 459.77 mmol) was added to it at 0 C and the resulting reaction mixture was stirred for 12 h. at 25 C. Reaction mixture was diluted with water and extracted with ethyl acetate (4 x 500 mL). Organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford rude mass which was purified by column chromatography using silica gel (100-200 mesh) and 10% EtOAc-hexane as eluent to afford 2-bromo-3-methoxymethoxy-pyridine (45 g) as pale brown liquid. 1H-NMR (400 MHz, DMSO-d6): delta 8.03 (dd, ‘ = 4.5 Hz, J” = 1.3 Hz, 1H), 7.60 (dd, J’ = 8.1 Hz, J” = 1.1 Hz, 1H), 7.40 (dd, J’ = 8.2 Hz, J” = 4.5 Hz, 1H), 5.35 (s, 2H), 3.41 (s, 3H).

The synthetic route of 6602-32-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CURADEV PHARMA PVT. LTD.; MIDDYA, Sandip; YADAV, Dharmendra B; SHRIVASTAVA, Ritesh; RAINA, Sushil; BANERJEE, Monali; SURYA, Arjun; (74 pag.)WO2016/27241; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 55676-22-7, 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. 55676-22-7, name is 3-Acetyl-6-chloropyridine. A new synthetic method of this compound is introduced below.

2 g (11.57 mmol) of 1-(6-chloropyrid-3-yl)ethanone and 70 mL of ammonium hydroxide are placed in a Parr reactor. The solution is heated at 130 C. overnight. The mixture obtained is evaporated to dryness, and the residue is taken up in ethyl acetate and washed with water and with saturated NaCl solution. The organic phase is dried over sodium sulfate and evaporated to dryness to give 1.14 g of 1-(6-aminopyrid-3-yl)ethanone, the characteristics of which are as follows: LC/MS (method G): ESI+ [M+H]+: m/z 137 tr (min)=0.35 1H NMR (300 MHz, delta in ppm, CDCl3): 2.41 (s, 3H), 6.45 (d, 1H), 6.88 (s, 2H), 7.86 (d, 1H), 8.58 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55676-22-7, 3-Acetyl-6-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; El-Ahmad, Youssef; Filoche-Romme, Bruno; Ganzhorm, Axel; Marciniak, Gilbert; Muzet, Nicolas; Ronan, Baptiste; Vivet, Bertrand; Zerr, Veronique; US2015/183804; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 884494-81-9, name is 3-Bromo-5-fluoro-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H5BrFNO

To a solution of 18.0 g (87.4 mmol) of 3-bromo-5-fluoro-2-methoxypyridine in 63 mL of anhydrous THF was added 67.0 mL (87.1 mmol, 1 .3 M in THF) of i-PrMgCI LiCI slowly at 0 C. The mixture was stirred at rt under Ar atmosphere for 4 h.To a stirred solution of 12.6 g (43.6 mmol) of compound 17-1 in 10 mL of DCM was added 130 mL of the above Grignard reagent (-0.4 M in THF) at -78 C. The mixture was stirred at rt under Ar atmosphere overnight, then quenched by addition of 200 mL of saturated NH4CI at 0 C. The organic phase was separated, dried over anhydrous Na2S04. After filtration, the filtrate was concentrated to afford a residue, which was purified by Ci8column eluting with 0 to 30 % gradient of ACN in H20 (0.5 % NH4HCO3) to afford compound 17-2. LC-MS: m/e = 417 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 884494-81-9.

Reference:
Patent; ANGEX PHARMACEUTICAL, INC.; WU, Wen-Lian; YANG, Zhiqiang; LEE, Francis; TAN, John Qiang; (112 pag.)WO2019/94143; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 65001-21-0, 5-Bromopyridine-3-sulfonyl chloride, 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, 65001-21-0, blongs to pyridine-derivatives compound. Safety of 5-Bromopyridine-3-sulfonyl chloride

Crude 5 -bromopyridine-3-sulfonyl chloride from step 1 above was dissolved in THF (14 L, 8 vol) and then transferred to a 20 L RB flask equipped with mechanical stirrer under inert atmosphere. The solution was cooled to 0-5C and tert- butyl amine (1.95 Kg, 26.66 moles) was added at 0-5C. Upon completion of addition, the reaction mixture was warmed to ambient temperature where it stirred for 2 h. At the conclusion of this period, the reaction progress was monitored by HPLC, which indicated that the reaction was complete. The solvent was evaporated under vacuum to give a thick residue. The residue was dissolved in ethyl acetate (18 L, 12 vol). The organic layer was separated, washed with water (9 L, 5 vol) and then concentrated under vacuum to yield a residue. Hexanes (9 L, 5 vol) were added to the residue and the product precipitated out and was collected by filtration to yield a free flowing yellow solid (1.5 Kg, 54.28% overall yield). ¾ NMR (DMSO-D6, 400 MHz, delta ppm); 8.99 (d, J = 2Hz, 1H), 8.81 (d, J= 2 Hz, 1H), 8.29 (t, J= 2Hz, 1H). [M++l] = 293.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,65001-21-0, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; JOHNSON, James A.; LLOYD, John; FINLAY, Heather; JIANG, Ji; NEELS, James; DHONDI, Naveen Kumar; GUNAGA, Prashantha; BANERJEE, Abhisek; ADISECHAN, Ashokkumar; WO2011/28741; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 98198-48-2, 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. 98198-48-2, name is 2-Amino-5-bromo-4-methylpyridine. A new synthetic method of this compound is introduced below.

Nitric acid (0.7 ml) was added dropwise to a solution of 5-bromo-4-methylpyridine-2-amine (2.0 g) in concentrated sulfuric acid (8.7 ml) at 55 C. over 30 minutes, and the mixture was stirred at the same temperature for 3 hours. After further stirring at room temperature for 2 hours, the reaction solution was poured into ice water. A 50% aqueous sodium hydroxide solution was added, and the resulting precipitate was collected by filtration, washed with distilled water and then dried under reduced pressure to give the title compound (2.5 g).MS (ESI) m/z: 268 (M+H)+.1H-NMR (CDCl3) delta: 2.54 (3H, s), 5.83 (2H, brs), 8.29 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98198-48-2, 2-Amino-5-bromo-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Daiichi Sankyo Company, Limited; US2011/82138; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 93683-65-9, name is 6-Chloro-3-nitropicolinonitrile, molecular formula is C6H2ClN3O2, 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. category: pyridine-derivatives

Method A: To a solution of delta-chloro^-cyano-S-nitro-pyridine (3.03 g, 16.5 mmol) in ethanol (166 ml) and H2O (16 ml) was added iron (165 mmoi, 9.2 g) and calcium chloride (2.75 g, 24.8 mmol). The reaction mixture was refluxed for 4 hours and then cooled down to room temperature. The precipitate was filtered off over Celite and the filtrate was evaporated to dryness. The residue was redissolved in ethyl acetate and extracted with brine. The aqueous layer was extracted back with ethyl acetate. The combined organic layers were evaporated in vacuo. The residue was adsorbed on silica and purified by silica gel column chromatography, the mobile phase being a ethyl acetate/hexane mixture in a ratio of 3:7, resulting in the pure title compound (1.89 g, yield 67 %) which was characterised by its mass spectrum as follows: MS (m/z): 172, 174 ([M+H]+, 100).Method B: To a suspension of 6-chloro-3-nitro-pyridine-2-carbonitrile (9.2 g, 50 mmol) in water (100 ml), was added 20 ml of a 25 % ammonia aqueous solution. The mixture was stirred at room temperature for 20 minutes. Then, Na2S2O4 (50 g, 86 %, 150 mmol) was added portion wise, and the mixture was stirred at room temperature for another 2 hours. The precipitate formed was collected by filtration, washed two times with cold water (10 ml) and then dried over P2O5, resulting in the title compound (7.0 g, yield 81 %) as a yellowish solid which was characterized by its mass spectrum as follows: MS (m/z): 172.1 ([M+H]+, 100).; Example 222 – synthesis of S-amino-e-chloro-pyridine^-carboxamideEither of the two following methods may be used:Method A: to a suspension of theta-chloro-S-nitro-pyridine^-carbonitrile (4 g, 22 mmol) in water (40 ml) was added a 33 % aqueous solution of ammonia in water (8.8 ml). This suspension was stirred at room temperature for 30 minutes. Then, sodium dithionite (21.8 g, 124 mmol) was added portion wise. The resulting mixture was stirred for another 2 hours at room temperature. The precipitate was filtered off and washed with a small amount of water, yielding the title compound (2.7 g, yield: 72 %). MS (m/z): 172, 174 ([M+H]+, 100).Method B: to a suspension of e-chloro-S-nitro-pyridine^-carbonitrile (11.01 g, 60 mmol) in methanol (120 ml), was added Raney-Nickel (3 g, washed with methanol EPO to remove water) and the mixture was shaken under a H2-atmosphere at room temperature for 4 hours. The catalyst was removed by filtration, washed with methanol (500 ml). Both filtrates were combined and then evaporated to dryness. The residue was dissolved in dichloromethane and the solution was filtered through a short and wide column with silica gel (100 g). The column was additionally washed with CH2CI2/Me0H (200 ml, 4:1). The filtrate and washings were combined and evaporated to small volume. The formed precipitate was filtered off to give 3-amino-6- chloro-pyridine-2-carboxamide (8.1 g). The final filtrate was evaporated to dryness and the residue purified by column chromatography on silica gel (30 g). The compound was eluted with the following solvent systems: CH2CI2 (200 ml), CH2CI2/Me0H 100:1 (200 ml). The appropriate fractions were evaporated in vacuo yielding an additional 1.15 g of S-amino-theta-chloro-pyridine^-carboxamide (total yield : 9.25 g, i.e. 90 %) which was characterised as follows:- M.p. 176-177C; – UV (MeOH): 212 (3.76), 256 (4.14), and 348 (3.76); and- elemental analysis: calculated for C6H6CIN3O (171.6): C 42.00 H 3.52 N 24.49. Found: C 42.42 H 3.54 H 24.11.

With the rapid development of chemical substances, we look forward to future research findings about 93683-65-9.

Reference:
Patent; 4 AZA Bioscience nv; WO2006/135993; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 462-08-8, Pyridin-3-amine, 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: Pyridin-3-amine, blongs to pyridine-derivatives compound. Recommanded Product: Pyridin-3-amine

To a solution of pyridin-3 -amine (2.5 g, 26.3 mmol) in anhydrous tetrahydiOfuran (80 mL) was added 1 M sodium bis(trimethylsilyl)amide in tetrahydrofuran (52.6 mL, 52.6 mmol) in a steady stream. The mixture was stirred for 30 minutes, treated dropwise with a solution of di-feri-butyl dicarbonate (5.92 g, 26.3 mmol) in anhydrous tetrahydrofuran (20 mL), stirred for 3 hours and concentrated. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium chloride, dried over anhydrous MgSCu, filtered, and concentrated by rotary evaporation. Purification by chromatography on silica eluting with 3%> methanol in dichloromethane afforded an amber semisolid. The material was dissolved in ethyl acetate, treated with decolorizing charcoal and vacuum filtered through diatomaceous earth. Concentration of the filtrate by rotary evaporation afforded the title compound as a light gold solid (4.35 g, 85%). MS (DCI+) m/z 195 (M+H)+.

The synthetic route of 462-08-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT GMBH & CO.KG; MARING, Clarence J.; PRATT, John K.; CARROLL, William A.; LIU, Dachun; BETEBENNER, David A.; HUTCHINSON, Douglas K.; TUFANO, Michael D.; ROCKWAY, Todd W.; SCHOEN, Uwe; PAHL, Axel; WITTE, Adreas; WO2012/87833; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1122-71-0 ,Some common heterocyclic compound, 1122-71-0, molecular formula is C7H9NO, 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 N3-methyl-N5-(( 15, 25)-2-methylcyclopropyl)-2-oxo- 1,2-dihydropyridine-3,5-dicarboxamide (42.8 mg, 0.17 mmol), (6-methylpyridin-2-yl)methanol (26.9 mg, 0.22 mmolcommercially available from, for example, Sigma-Aldrich) and 2- (tributylphosphoranylidene)acetonitrile (0.090 mL, 0.34 mmol; commercially available from, for example, TCI) in toluene (1 mL) in a sealed vial was heated at 100 C for 0.5 h in a microwave reactor. The volatiles were evaporated from the mixture under a stream of nitrogen and the residuewas redissolved in 3:1 methanol/DMSO (2 mL) and was purified by MDAP (2 x 1 mL injection, formic). The required fractions from both injections were combined, evaporated and dried in vacuo to give a dark brown oily residue. The residue was redissolved in 3:1 methanol/DMSO (1 mL) and was further purified by MDAP (1 x 1 mL injection, formic). The required fractions were combined, evaporated and dried in vacuo to give a pale yellow glass; N3-methyl-N5-((15,25)-2-methylcyclopropyl)-1-((6-methylpyridin-2-yl)methyl)-2-oxo- 1, 2-d ihydropyrid ine-3,5-d icarboxamide (42.2 mg, 0.12 mmol, 69 % yield).LCMS (2 mm formic) Rt = 0.63 mi m/z= 355 for [MH]

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. 1122-71-0, 6-Methyl-2-pyridinemethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; AYLOTT, Helen Elizabeth; COOPER, Anthony William James; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (308 pag.)WO2017/37116; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 75418-74-5, name is Methyl 3-oxo-3-(pyridin-2-yl)propanoate. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

a Pyridin-2-yl-propynoic acid ethyl ester The title compound was synthesised from commercially available 3-oxo-3-pyridin-2-yl-propionic acid methyl ester using the procedure described in Example 32, step (b), in 76% yield. 1H NMR (CDCl3) delta8.66 (d, J=4.8 Hz, 1H), 7.73 (m, 1H), 7.59 (d, J=7.8 Hz, 1H), 7.36 (m, 1H), 4.31 (q, J=7.1 Hz, 2H), 1.35 (t, J=7.1 Hz, 3H).

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, 75418-74-5, Methyl 3-oxo-3-(pyridin-2-yl)propanoate.

Reference:
Patent; 3-Dimensional Pharmaceuticals, Inc.; US2002/169200; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem