Tag: M.W=300-400

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. 757978-18-0, name is 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine

Into a 250 mL round bottomed flask were added 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (8.00 g, 40.6 mmol) and 120 mL dry THF. The solution was cooled in an ice bath at 0 C and NaH (2.40 g, 60.0 mmol) was added in three portions. After 20 min, />-toluenesulfonyl chloride (8.70 g, 45.63 mmol) was added, and the reaction mixture was allowed to warm to rt over 30 min. The reaction mixture was concentrated and hexanes was added to obtain a precipitate, which was collected and washed with ice cold 2M NaOH. The crude product was recrystallized from EtOAc/hexanes to afford 17.8 g (92%) of the title compound as a light tan powder. 1H-NMR (500 MHz, ^6-DMSO) delta 8.49 (d, J=2.5 Hz, 1H), 8.21 (s, 1H), 7.99 (d, J=2.0 Hz , 1 H), 7.98(d, J=8.5 Hz , 2H), 7.42 (d, J=8.5 Hz, 2H), 2.32(s, 3H); MS: m/z 476.8/478.8 [MH+].

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, 757978-18-0, 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; SGX PHARMACEUTICALS, INC.; WO2008/124849; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route 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.

To the reaction flask was added compound 39 (5.65 g, 18.34 mmol)Soluble in methanol,0.5 g Pd / C was added,Catalytic hydrogenation at room temperature,TLC tracking, to be completely complete,Diatomaceous earth, the solvent was removed by distillation under reduced pressure,To obtain a crude solid,And then petroleum ether: ether (30: 1) beating to get pink powder,4.75 g of compound 7-10 was obtained by drying,Yield: 93.1%.

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; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Zhang Yinsheng; Gao Yong; Ren Jing; Wang Qinglin; Wang Zhao; (67 pag.)CN106905245; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1335210-23-5, 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. 1335210-23-5, name is 1-(2,2-Dimethoxyethyl)-5-methoxy-6-(methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid, molecular formula is C13H17NO8, 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.

Step 1; A suspension of compound 11-A (965 mg, 3.061 mmol), 2,4,6- trifiuorobenzylamine (493 mg, 3.06 mmol), and HATU (1402 mg, 3.688 mmol) in CH2C12 (15 mL) was stirred in 0 C as DIEA (2 mL, 11.48 mmol) was added.After 1.5 hours at 0 C, the reaction mixture was diluted with ethyl acetate, and washed with water (twice). After the aqueous fractions were extracted with ethyl acetate, the organic fractions were combined, dried (Na2S04), and concentrated. The residue was purified by CombiFlash (40 g column) using hexanes-ethyl acetate as eluents to obtain compound 11-B. 1H NMR (400 MHz, Chloroform-d) delta 10.30 (t, J = 5.9 Hz, 1H), 8.40 (s, 1H), 6.79 – 6.51 (m, 2H), 4.65 (d, J = 5.6 Hz, 2H), 4.48 (t, J = 4.8 Hz, 1H), 4.01 (d, J = 4.8 Hz, 2H), 3.97 (s, 3H), 3.94 (s, 3H), 3.38 (s, 6H). 19F NMR (376 MHz, Chloroform-d) delta – 109.07 – -109.35 (m, IF), -1 1 1.93 (t, J = 6.9 Hz, 2F). LCMS-ESI+ (m/z): [M+H]+ calculated for C20H22F3N2O7: 459.14; found: 459.2.

According to the analysis of related databases, 1335210-23-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; JI, Mingzhe; LAZERWITH, Scott E.; PYUN, Hyung-Jung; WO2015/6731; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 874302-76-8, 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 874302-76-8 as follows.

Weigh 61.2mg (0.06mmol) compound 39,64.3mg (0.18mmol) compound 37,9.8mg (0.08mmol) DMAP, was added to a 25ml eggplant-shaped flask, add 5ml DCM was dissolved under argon atmosphere, stirred at room temperature 48h, DCM was evaporated to dryness under reduced pressure and, add acetonitrile dissolved, purified by preparative liquid phase to give product 51.3mg

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,874302-76-8, its application will become more common.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Liu Keliang; Feng Siliang; Chen Kuncheng; Guo Xiaopeng; Meng Qingbin; Zhou Ning; (23 pag.)CN104370862; (2019); B;,
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 76093-33-9, name is (R)-5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C16H16N2O6

(7) Preparation of (4S)-3-[1-(3,3-diphenylpropyl)-3-methylpyrrolidin -3-yl] 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate To a solution of (R)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (67.5g, 0.2mol) in dichloromethane was added 1.5mL DMF. To the mixture was slowly added oxalyl chloride (51g, 0.4mol) dropwisely in an ice bath. The reaction was conducted at 25C. After the completion of reaction, the resulting mixture was evaporated under reduced pressure to remove oxalyl chloride. To the reaction flask were slowly added dichloromethane (300mL), 1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-ol (29.5g, 0.1mol) and DIPEA (25.8g, 0.2mol) dropwisely under cooling in an ice bath respectively and successively. The reaction was conducted at 25C. 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 = 80:1 (volumetric ratio)) to produce (4S)-3-[1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-yl] 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (34 g) in a yield of 56 %.

With the rapid development of chemical substances, we look forward to future research findings about 76093-33-9.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; ZHANG, Hui; FAN, Mingwei; SUN, Liang; EP2703398; (2014); 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.152460-09-8, name is N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine, molecular formula is C16H13N5O2, molecular weight is 307.31, as common compound, the synthetic route is as follows.Application In Synthesis of N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine

In to a hydrogenation kettle a N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2- pyridineamine (20 g; 0.0.0651 mol) obtained from step-B and methanol (400ml) were added. Wet Raney’s nickel (8g) was washed thoroughly with water and was charged into hydrogenation kettle. Hydrogenation was conducted at 60psi at 25C for 45hours. The reaction mixture was filtered and washed with methanol (200ml). The combined filtrates were concentrated in vacuum, treated with a mixture of water (100ml) and chloroform (200 ml). The organic layer was washed with water (3x50ml) and distilled under vacuum. Residual solid was brought to room temperature and ethyl acetate (150ml) was charged. The solution was heated to reflux temperature and cooled down with stirring to 0-5C. The crystalline solid was filtered off and washed with chilled ethyl acetate (10ml), dried to afford title compound (15.0g, yield: 82.7%) of the title product. Purity (by HPLC): 99.40%) Melting point: 143-147C

At the same time, in my other blogs, there are other synthetic methods of this type of compound,152460-09-8, N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; NATCO PHARMA LIMITED; KOMPELLA, Amala Kishan; RACHAKONDA, Sreenivas; GAMPA, Venu Gopala Krishna; ADIBHATLA, Kali Satya Bhujanga Rao; NANNAPANENI, Venkaiah Chowdary; WO2013/35102; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1335210-23-5, 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 1335210-23-5 as follows.

Examples 9 and 10 Preparation of Compounds 9 and 1Theta (2S,5R,13aS)-N-((R)-H4-fluoroph^ octahydro-2,5-methanopyrido[ 1 ‘,2′:4,5]pyrazino[2, 1 -b][ 1 ,3]oxazepine- 10-carboxamide 9 and (2R,5S,13aR)-N-((R)-l-(4-fj.uorophenyl)ethyl)-8-hydroxy-7,9-dioxo- 2,3,4,5 J,9,13,13a-octahydro-2,5-methanopyrido[r,2’:4,5]pyrazino[2, b] [ 1 ,3]oxazepine- 10-carboxamide 10 Step 1 l-(2,2-dimethoxyethyl)-5-methoxy-6-(methoxycarbonyl)-4-oxo-l ,4- dihydropyridine-3-carboxylic acid (1-A, 0.500 g, 1.59 mmol), was suspended in acetomtrile (6 rnL) and treated with N,N-diisopropylethylamine (DIPEA) (0.550 mL, 3.17 nifflol), (R)-l-(4-fluoropbenyi)ethanamine (0.242 rng, 1.74 mmol) and HATXJ (0.661 g, 1.74 mmol). The reaction mixture was stirred for 2 hours and partitioned between ethyl acetate and water. The organic layer was separated and washed with HCl ( 10% aq), sodium bicarbonate (1 M aq), dried over sodium sulfate, filtered and concentrated to afford crude (R)-methyl l -(2,2-dimethoxyethyl)-5-(l -(4- fiuorophenyl)ethylcarbamoyl)-3-methoxy-4-oxo-l ,4-dihydropyridine-2-carboxylate which was used without purification in the next step: LCMS-ESI+ (m/z): [M+H] ; calculated for C”.< ; i ^ X -()··: 437.17; found: 437.1. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1335210-23-5, its application will become more common. Reference:
Patent; GILEAD SCIENCES, INC.; JIN, Haolun; LAZERWITH, Scott, E.; MARTIN, Teresa, Alejandra, Trejo; BACON, Elizabeth, M.; COTTELL, Jeromy, J.; CAI, Zhenhong, R.; PYUN, Hyung-Jung; MORGANELLI, Philip, Anthony; JI, Mingzhe; TAYLOR, James, G.; CHEN, Xiaowu; MISH, Michael, R.; DESAI, Manoj, C.; WO2014/100323; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 154048-89-2 , The common heterocyclic compound, 154048-89-2, name is N-Boc-3-Amino-4-iodopyridine, molecular formula is C10H13IN2O2, 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 resealable pressure vessel was charged with tert-butyl tert-butyl (4-iodopyridin-3-yl)carbamate (1.54 g, 4.8 mmol), ((prop-2-yn-1-yloxy)methyl)benzene (0.84 g, 5.8 mmol), bis(triphenylphosphine) palladium(II) chloride (0.17g, 0.24 mmol), copper(I) iodide (0.09 g, 0.48mmol), triethylamine (15 mL, 108 mmol) and DMF (5 mL). The mixture was degassed by bubbling nitrogen through for several minutes, the flask was sealed and the reaction mixture was stirred for 7h.. The mixture was diluted with EtOAc and washed with saturated ammonium chloride (2x) and brine (1x). The organics were dried over sodium sulfate, filtered and evaporated, and the crude material purified by silica gel chromatography, eluting with 12-100% EtOAc in hexanes, affording tert-butyl (4-(3-(benzyloxy)prop-1-yn-1-yl)pyridin-3-yl)carbamate (1.6 g, 98%). 1H NMR (400MHz, CHLOROFORM-d) delta = 9.44 (s, 1H), 8.28 (d, J=4.8 Hz, 1H), 7.45 – 7.33 (m, 5H), 7.26 (d, J=4.8 Hz, 1H), 7.14 – 6.93 (m, 1H), 4.71 (s, 2H), 4.50 (s, 2H), 1.56 (s, 9H).

The synthetic route of 154048-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; McDonald, Ivar M.; Mate, Robert; Ng, Alicia; Park, Hyunsoo; Olson, Richard E.; Tetrahedron Letters; vol. 59; 8; (2018); p. 751 – 754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 76093-33-9 ,Some common heterocyclic compound, 76093-33-9, molecular formula is C16H16N2O6, 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 solution of (R)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (4.86g, 14.6mmol) in dichloromethane was added 0.1mL DMF. To the mixture was slowly added oxalyl chloride (3.68g, 29.0mmol) dropwisely in an ice bath. The reaction was conducted at 25C 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 (20mL), the crude product of 1-(3,5-difluorobenzyl)-3-methylpyrrolidin-3-ol (1.8g) and DIPEA (1.86g, 14.4mmol) dropwisely under cooling in an ice bath respectively and successively. The reaction was conducted at 25C. 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 = 85:1 (volumetric ratio)) to produce (4S)-3-[1-(3,5-difluorobenzyl)-3-methyl-3-pyrrolidin-3-yl] 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (1.78 g) in a yield of 45.6% (two steps together). Molecular formula: C28H29F2N3O6 Mw: 541.2 MS (M+H): 543.3 1H-NMR(DMSO, 400 MHz) delta: 9.14 (1 H, t), 8.02-7.97 (2 H, m), 7.60-7.55 (2 H, m), 7.39-7.33 (2 H, m), 4.93-4.90 (1 H, d), 4.41-4.40 (2 H, m), 3.56-3.53 (6 H, m), 3.35 (1 H, s), 3.07 (1 H, s), 2.30-2.26 (6 H, m), 1.50-1.24 (3 H, dd), 1.10 (3 H, s).

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. 76093-33-9, (R)-5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; ZHANG, Hui; FAN, Mingwei; SUN, Liang; EP2703398; (2014); 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. 117977-21-6, name is 2-[[[4-(3-Methoxypropoxy)-3-methylpyridine-2-yl ]methyl]thio]-1H-benzimidazole, molecular formula is C18H21N3O2S, 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. COA of Formula: C18H21N3O2S

50 g of 2-[4-(3-methoxy propoxy-3-methylpyridine-2-yl) methyl thio]- lH-benzimidazole was taken in 100 ml acetonitrile. To this mixture 185.2 g (0.95mol) sodium hypochlorite was added drop wise between 0-50C in a nitrogen atmosphere and the obtained mixture was stirred at 0-50C for 30 minutes. After completion of reaction, the pH of reaction mixture was adjusted to 9.0 by using 5 % acetic acid. The mixture was extracted with methylene dichloride, and the extract was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and dried under vacuum. The obtained residue was dissolved in 20 ml of methylene dichloride followed by t-butyl methyl ether to get the clear solution. Stir the mass for one hour at room temperature to get the precipitate. Filtered the precipitated product and washed with 100 ml of t-butyl methyl ether. Dry the product at 600C under vacuum to obtain title compound 41 g (78.25%) as off white solid

With the rapid development of chemical substances, we look forward to future research findings about 117977-21-6.

Reference:
Patent; IPCA LABORATORIES LIMITED; WO2009/116072; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem