Tag: M.W=300-400

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. 641569-94-0, name is 4-Methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid, molecular formula is C17H14N4O2, 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. Computed Properties of C17H14N4O2

Example 13; Preparation of 3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)-4-methylbenzoyl chloride, dihydrochloride of the formula (X-Cl).2HCl:Thionyl chloride (1400 ML) was added to 3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)-4-methylbenzoic acid of formula X (39 gms). This mixture was heated to 60-70 C. and stirred for 10-12 hours. The reaction mixture was then cooled to 30-27 C. The obtained slurry was filtered and the solid was washed with dichloromethane. The wet product was dried at 55-60 C. under reduced pressure. Dry wt: 140 gm Yield: 95.4 Purity: above 98% by HPLC Hydrochloride content (by Argentometry titration): 27.48%

With the rapid development of chemical substances, we look forward to future research findings about 641569-94-0.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; US2010/16590; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 76093-33-9, (R)-5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid, 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, 76093-33-9, blongs to pyridine-derivatives compound. Recommanded Product: (R)-5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

(2) Preparation of (4S)-3-(3-methyl-1-phenylethylpyrrolidin-3-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate According to Example 15, (R)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid was synthesized. To a solution of (R)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (2.9 g, 8.73 mmol) in dichloromethane was added 0.1 mL DMF. To the mixture was slowly added oxalyl chloride (2.2 g, 17.33 mmol) dropwisely in an ice bath. The reaction was conducted at 25 C. until the completion of reaction. The resulting mixture was evaporated under reduced pressure to remove oxalyl chloride. To the reaction flask were slowly added dichloromethane (20 mL), 3-methyl-1-phenylethylpyrrolidin-3-ol (1 g, 4.87 mmol) and DIPEA (1.56 g, 12.1 mmol) dropwisely under cooling in an ice bath respectively and successively. The reaction was conducted at 25 C. After the completion of reaction monitored by HPLC, the reaction solution was washed with water thrice. The organic phase was dried over sodium sulfate, and filtered by suction. The filtrate was evaporated to dryness, and purified by column chromatography (silica gel column, eluted with petroleum ether:ethyl acetate=78:1 (volumetric ratio)) to produce (4S)-3-(3-methyl-1-phenylethylpyrrolidin-3-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (1.21 g) in a yield of 48%. Molecular formula: C29H33N3O6 Mw: 519.2 MS (M+H): 520.3 1H-NMR (DMSO, 400 MHz) delta: 9.20-9.18 (1H, d), 8.03-7.97 (2H, m), 7.64-7.53 (2H, m), 7.34-7.21 (5H, m), 4.96-4.93 (1H, d), 3.56-3.54 (2H, m), 3.52-3.41 (3H, m), 3.34-3.17 (1H, m), 3.07-2.93 (2H, m), 2.50-2.49 (2H, m), 2.31-2.29 (6H, d), 2.26 (1H, m), 1.54-1.39 (3H, dd), 1.1 (1H, s), 1.05 (1H, t).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76093-33-9, its application will become more common.

Reference:
Patent; XUANZHU PHARMA CO., LTD.; Zhang, Hui; Fan, Mingwei; Sun, Liang; US2014/45896; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1206102-07-9, 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. 1206102-07-9, name is Methyl 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate. A new synthetic method of this compound is introduced below.

A reactor was charged with (3.759 kg, 11.27 mol) of methyl 1-(2,3-dihydroxypropyl)-4-oxo- 3-[(phenylmethyl)oxy]-1 ,4-dihydro-2-pyridinecarboxylate 7 and 18.8 L of DMF. To this agitated mixture at 18-20 0C was added N-bromosuccinimide (2.220 kg, 12.47 mol) over 20 minutes via a powder funnel. The resultant mixture was stirred at rt for 16 h. At this time less than 1% of starting material was present by HPLC. The mixture was worked up in half batches by cooling to 10 0C and added an ice/water mixture (12 kg ice in 35 kg deionized water) and the mixture was agitated, then filtered. This was repeated for the second half of the batch. The combined filter cake was washed with 14 L of water and dired in a vaccum oven to provide 4.033 kg of methyl 5-bromo-1-(2,3-dihydroxypropyl)-4- oxo-3-[(phenylmethyl)oxy]-1 ,4-dihydro-2-pyridinecarboxylate 19 (91.6%) as an off-white powder of 99.2% HPLC purity. 1H NMR(300 MHz, Methanol-d4) delta 8.21 (s, 1 H), 7.41-7.33 (m, 5 H), 5.16 (s, 2 H), 4.17 (dd, J = 14.3, 2.4 Hz, 1 H), 3.90 (dd, J = 14.3, 9.0 Hz, 1 H), 3.81 (s, 3 H), 3.78 (m, 1 ), 3.52 (dd, J = 11.3, 4.8 Hz, 1 H), 3.41 (dd, J = 11.3, 6.3 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1206102-07-9, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; SHIONOGI & CO., LTD.; JOHNS, Brian, Alvin; DUAN, Maosheng; HAKOGI, Toshikazu; WO2010/68262; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 571189-16-7, 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. 571189-16-7, name is tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate. A new synthetic method of this compound is introduced below.

Add 100 ml of methanol, 0.10 g of 10% palladium carbon to 100 ml of the reaction vessel, and add 1.8 g of 4-(6-nitropyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester. The system is closed and nitrogen-filled to 0.3. MPa, replacement twice, pass H2 to the reactor pressure 0.3MPa, replace once, then start the reaction at room temperature, reaction 12h, HPLC analysis of the reaction solution, the raw material content is less than 0.5%. The reaction solution was filtered under reduced pressure through a 0.45 um organic filter, and then evaporated to dryness to give a white solid 1.71 g, product yield 95%, purity over 99%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,571189-16-7, tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Suzhou Laikeshide Pharmaceutical Co., Ltd.; Wang Aifeng; Liu Chuantao; Zhang Caihui; Yu Jurong; (7 pag.)CN108558745; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 122368-54-1, 2-((4-Chlorophenyl)(piperidin-4-yloxy)methyl)pyridine, 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, 122368-54-1, blongs to pyridine-derivatives compound. Product Details of 122368-54-1

To 10 mL of DMF were added 0.5 g of vanillic acid, 0.51 g of EDC, 0.44 g of HOBt, 1.44 mL of TEA and 0.99 g of 2-[(4-chlorophenyl)(4-piperidinyloxy)methyl]pyridine, and the mixture was stirred at 60 to 80C for 4 hours. 10 mL of EtOAc and 10 mL of purified water were added to the reaction mixture and the layers were separated. The aqueous layer was extracted once with 10 mL of EtOAc and the aqueous layer was discarded. The organic layer was washed three times with 10 mL of purified water, dried over Na2SO4 and filtered. The filtrate was distilled under reduced pressure and purified by flash column chromatography to obtain 0.40 g of the title compound as a pale yellow solid. Yield: 31.6% 1H NMR (400MHz, DMSO-d6) delta 9.41 (brs, 1H), 8.47 (d, J = 4.0 Hz, 1H), 7.81 (t, J = 7.0, 1H), 7.57(d, J = 8.0 Hz, 1H), 7.44?6.94(m, 6H), 6.84?6.67(m, 3H), 5.71(s, 1H), 3.87(s, 3H), 3.74?3.69(m, 2H), 3.37(brs, 2H), 1.85(brs, 2H), 1.72(brs, 2H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,122368-54-1, its application will become more common.

Reference:
Patent; Shin Poong Pharmaceutical Co., Ltd.; RYU, JeiMan; LEE, Dong Won; LEE, Kang Hyeok; PARK, Jin Hun; CHO, Geum Sil; LEE, Ki Sung; CHUNG, Jin Ho; PARK, Woo Ile; LEE, Jae Young; (35 pag.)EP3345910; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 571189-16-7, 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. 571189-16-7, name is tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate. A new synthetic method of this compound is introduced below.

Example 101h tert-Butyl 4-(6-Aminopyridin-3-yl)piperazine-1-carboxylate 101h A 500-mL bottle was purged with nitrogen and charged with tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate 101g (3.1 g, 10 mmol), 10% palladium on carbon (50% wet, 1.0 g) and ethanol (100 mL). It was evacuated, charged with hydrogen gas, and stirred for 16 h at room temperature. The hydrogen was then evacuated and nitrogen was charged into the bottle. The catalyst was removed by filtration through a pad of CELITE and the filtrate concentrated under reduced pressure to afford 101h (2.7 g, 97%). MS: [M+H]+ 279

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,571189-16-7, its application will become more common.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 152460-09-8, 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. 152460-09-8, name is N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine. A new synthetic method of this compound is introduced below.

General procedure: A mixture of the organic nitro compound (1.0 mmol), NH2NH2¡¤H2O (2.5 equiv.) and H2O2-treated AC powder (50 wt%) in DMF (1.5 mL) was stirred vigorously magnetically at 100 C. The reaction was monitored by LC-MS or GC-MS. On completion the reaction mixture was filtered to remove the catalyst. The combined organic mixture material was dried using anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure to obtain the products. All the compounds were known and characterised by their 1H NMR and MS spectra and comparison with literature data.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,152460-09-8, its application will become more common.

Reference:
Article; Jiang, Yuqin; Suo, Huajun; Zhang, Dandan; Li, Xiyong; Sun, Yamin; Ren, Baoqi; Zhang, Weiwei; Xu, Guiqing; Journal of Chemical Research; vol. 41; 9; (2017); p. 509 – 512;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 877060-48-5 , The common heterocyclic compound, 877060-48-5, name is tert-Butyl 3-iodo-1H-pyrrolo[3,2-c]pyridine-1-carboxylate, molecular formula is C12H13IN2O2, 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.

1.1 140 mg (0.20 mmol) of bis(triphenylphosphine)palladium(II)chloride and 15 mg (0.08 mmol) of copper(I)iodide are added to a solution, kept under nitrogen, of 1.37 g (4.00 mmol) of tert-butyl 3-iodopyrrolo[3,2-c]pyridine-1-carboxylate (prepared by the method of M. Lefoix et al, Synthesis, 2005, 20, 3581-3588) in 20 ml of tetrahydrofuran. Carbon monoxide is passed into this solution in an autoclave apparatus, and the mixture is stirred at a pressure of about 5 bar for 50 minutes. The apparatus is decompressed, 589 mg (6.00 mmol) of trimethylsilylacetylene and 405 mg (4.00 mmol) of triethylamine are added under nitrogen. The apparatus is re-pressurised to 5.8 bar with carbon monoxide, and the reaction mixture is stirred at room temperature for 45 hours. Saturated sodium chloride solution is added to the reaction mixture, which is then extracted with dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with petroleum ether/ethyl acetate as eluent: tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo-[3,2-c]pyridine-1-carboxylate as yellowish crystals; ESI 343.1.2 104 mg (0.75 mmol) of potassium carbonate are added to a solution of 103 mg (0.30 mmol of tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo-[3,2-c]pyridine-1-carboxylate and 148 mg (0.75 mmol) of phenylguanidine carbonate in 1.5 ml of ethylene glycol monomethyl ether, and the mixture is heated at the boil for 68 hours. After cooling, 10 ml of water are added, and the mixture is stirred at 40 C. for 1 h. The precipitate formed is filtered off with suction, washed with water and dried in vacuo, giving phenyl-[4-(1H-pyrrolo[3,2-c]pyridin-3-yl)pyrimidin-2-yl]amine (?A1?) as pale-brown solid; ESI 287;1H NMR (DMSO-d6) delta [ppm] 6.90 (t, J=7.5 Hz, 1H), 7.25 (m, 3H), 7.39 (d, J=5.5 Hz, 1H), 7.76 (d, J=7.5 Hz, 2H), 8.22 (d, J=5.5 Hz, 1H), 8.32 (d, J=5.5 Hz, 1H), 8.35 (s, 1H), 9.46 (s, 1H), 9.81 (s, 1H), 12.0 (bs, 1H).

The synthetic route of 877060-48-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GESELLSCHAFT; US2011/92527; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 571189-16-7 ,Some common heterocyclic compound, 571189-16-7, molecular formula is C14H20N4O4, 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.

Step 2: Synthesis of tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate 10% palladium/carbon catalyst (0.50 g) was added to a solution of tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate (2.85 g, 9.24 mmoL) in methanol (150 mL). The mixed solution was stirred under a hydrogen atmosphere (1 atm) at room temperature for 24 h, and filtered through Celite. The filtrate was concentrated under reduced pressure to obtain tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate (2.12 g, yield: 82.5%).

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. 571189-16-7, tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; WANG, Shulong; CHEN, Kuncheng; LIU, Xijie; HU, Yuandong; LIU, Bo; PENG, Yong; LUO, Hong; HAN, Yongxin; WANG, Shanchun; LIU, Mei; XU, Hongjiang; (38 pag.)EP3434676; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 154048-89-2, Adding some certain compound to certain chemical reactions, such as: 154048-89-2, name is N-Boc-3-Amino-4-iodopyridine,molecular formula is C10H13IN2O2, 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 154048-89-2.

To a solution of (4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester (280 mg, 875 mumol) in DMF (4 mL) was added NaH (42.0 mg, 962 mumol, 60% dispersion in mineral oil) at 0 C. The reaction mixture was stirred at room temperature for 30 minutes. 2,2,2-Trifluoroethyl trifluoromethanesulphonate (203 mg, 126 muL, 875 mumol, CAS RN 6226-25-1) was added and the reaction stirred at room temperature for 2 hours. The reaction mixture was poured on 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc and the combined organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 30:70). Colorless solid (207 mg, 59%). MS (ESI): m/z=403.012 [M+H]+.

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. 154048-89-2, N-Boc-3-Amino-4-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bissantz, Caterina; Dehmlow, Henrietta; Erickson, Shawn David; Karnachi, Prabha Saba; Kim, Kyungjin; Martin, Rainer E.; Mattei, Patrizio; Sander, Ulrike Obst; Pietranico-Cole, Sherrie Lynn; Richter, Hans; Ullmer, Christoph; US2012/232051; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem