Day: July 16, 2021

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.102368-13-8, name is 1,1′-Thiocarbonylbis(pyridin-2(1H)-one), molecular formula is C11H8N2O2S, molecular weight is 232.2584, as common compound, the synthetic route is as follows.HPLC of Formula: C11H8N2O2S

Steps b, c : N-((cis)-3-isothiocyanatocyclobutyl)-3-(4-methoxyphenyl)bicyclo[1.1.1]pentane-1-carboxamide. A similar procedure to that described for the synthesis of N-(cis-(3-isothiocyanatocyclobutyl))-5-methoxy-[2,3′-bipyridine]-6′-carboxamide step c) and step d) was followed by using tert-butyl((cis)-3-(3-(4-methoxyphenyl)bicyclo[1.1.1]pentane1carboxamido) cyclobutyl) carbamate (58.0 mg, 0.15 mmol) to produce N-((cis)-3-isothiocyanatocyclobutyl)-3-(4-methoxyphenyl)bicyclo[1.1.1]pentane-1-carboxamide (26.0 mg, 52%). 1H NMR (400 MHz, CDCl3): delta 7.14 (d, J=8.0 Hz, 2H); 6.67 (brs, 1H); 5.75-5.63 (brs, 1H); 4.25-4.13 (m, 1H); 3.90-3.81 (m, 1H); 3.80 (s, 3H); 2.95-2.70 (m, 2H); 2.25 (s, 6H); 2.24-2.15 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,102368-13-8, 1,1′-Thiocarbonylbis(pyridin-2(1H)-one), and friends who are interested can also refer to it.

Reference:
Patent; Northeastern University; Malamas, Michael S.; Makriyannis, Alexandros; Farah, Shrouq I.; Zvonok, Alexander M.; Alapafuja, Shakiru Olajire; (47 pag.)US2019/345132; (2019); 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. 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., Quality Control of N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine

170 L of Cone. Hydrochloric acid is charged into the reactor. 70 Kg of stannous chloride dihydrate is charged. Stirred for 10 minutes. Cooled the reaction mass to 0-5C. Added compound of the formula (VI) slowly during 3-4 hours at 0-5 C. reaction mass is brought to 25-35C. Maintained 1 V2 hour at 25-35C. Charged 500 Its of DM water to the reaction mass and charged slowly 400 L of 50% sodium hydroxide solution at 25-3 5C. Reaction mass is extracted with 2 x 250 L chloroform. The chloroform layer is water wash thoroughly and carbon treatment is given . Distilled off chloroform completely under vacuum and charged 20 L ethyl acetate. Cooled to 0-10C. Maintained 1 hour at 0-10C. Centrifuged and washed with 10 L ethyl acetate to provide N-(5-amino-2-methyl phenyl)-4-(3-pyridyl)-2-pyrimidineamine of the formula [VII]Yield: 10 Kg (61.5%)MR: 141-144C.PuritybyHPLC:99.8%.Step -3:The preparation of N-(5-amino-2-methyl phenyl)-4-(3-pyridyl)-2-pyrimidineamine (VII)20 L of Cone. Hydrochloric acid is charged into the reactor. 7 Kg of stannous chloridedihydrate is charged. Stirred for 10 minutes. Cooled the reaction mass to 0-5C. Addedcompound of the formula (VI) slowly during 2-3 hours at 0-5C. reaction mass is broughtto 25-35C. Maintained 3 hours at 25-35C. Charged 500 Its of DM water to thereaction mass and charged slowly 40 L of 50% sodium hydroxide solution at 25-35C.Reaction mass is extracted with 2 x 35 L chloroform. The chloroform layer is waterwash thoroughly and carbon treatment is given . Distilled off chloroform completelyunder vacuum and charged 2 L ethyl acetate. Cooled to 0-10C. Maintained 1 hour at 0-10C. Centrifuged and washed with 1 L ethyl acetate to provide N-(5-amino-2-methylphenyi)-4-(3-pyridyl)-2-pyrimidineamine of the formula [VII]Yield: 0.98Kg(60%)MR: 140-143C.Purity by HPLC: 99.8%.Step -3: The preparation of N-(5-amino-2-methyl phenyl)-4-(3-pyridyl)-2-pyrimidineamine of theformula [VH] 17 L of Cone. Hydrochloric acid is charged into the reactor. 7 Kg of stannous chloride dihydrate is charged. Stirred for 10 minutes. Cooled the reaction mass to 0-5C. Added compound of the formula (VI) slowly during 2-3 hours at 0-5C. reaction mass is brought to 25-35C. Maintained 3 hours at 25-35C. Charged 500 Its of DM water to the reaction mass and charged slowly 40 L of 50% sodium hydroxide solution at 25-35C. Reaction mass is extracted with 2 x 50 L chloroform. The chloroform layer is waterwash thoroughly and carbon treatment is given . Distilled off chloroform completelyunder vacuum and charged 2 L ethyl acetate. Cooled to 0-10C. Maintainedl hour at 0-10C. Centrifuged and washed with 1 L ethyl acetate to provide N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine of the formula [VII]Yield : 0.97 Kg (60%)MR: 140-143C.Purity by HPLC: 99.7%. Step -3 ;The preparation of N-(5-amino-2-methyl phenyl)-4-(3-pyridyl)-2-pyrimidineamine of theformula [VII]19 L of Cone. Hydrochloric acid is charged into the reactor. 7 Kg of stannous chloridedihydrate is charged. Stirred for 10 minutes. Cooled the reaction mass to 0-5C. Addedcompound of the formula (VI) slowly during 2-3 hours at 0-5C. reaction mass is broughtto 25-35C. Maintained 2 1A hour at 25-35C. Charged 500 Its of DM water to thereaction mass and charged slowly 40 L of 50% sodium hydroxide solution at 25-35C.Reaction mass is extracted with 2 x 50 L chloroform. The chloroform layer is waterwash thoroughly and carbon treatment is given . Distilled off chloroform completelyunder vacuum and charged 2 L ethyl acetate. Cooled to 0-10C. Maintained 1 hour at 0-10C. Centrifuged and washed with 1 L ethyl acetate to provide N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine of the formula [VII]Yield: 1.05 Kg (64.5%)MR: 142-144C.Purity by HPLC: 99.85%.

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, 152460-09-8, N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine.

Reference:
Patent; NATCO PHARMA LIMITED; KOMPELLA, Amala; BHUJANGA RAO, Adibhatla, Kali, Sathya; VENKAIAH CHOWDARY, Nannapaneni; WO2004/108699; (2004); 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. 56026-36-9, name is Methyl 6-(hydroxymethyl)nicotinate, molecular formula is C8H9NO3, 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. Application In Synthesis of Methyl 6-(hydroxymethyl)nicotinate

A mixture of methyl 6-(hydroxymethyl)nicotinate (7 g , 37 mmol) and Mn02 (32,3 g , 372 mmol) in DCM ( 200 mL ) was stirred at 20 C for 4 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (PE/EtOAc = 5/1) to afford methyl 6-formylnicotinate (6 g , 97%).MS-ESI (m/z): 166.2 (M+l) + (LC-MS method C; Ret. time: 0.36 min).

With the rapid development of chemical substances, we look forward to future research findings about 56026-36-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); 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 159981-19-8, name is 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde

Step 1 – Synthesis of[5-(5-chloro-lH-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-[6-(2,2,2- trifluoro-ethoxy)-pyridin-3-ylmethyl]-amine (P-0409):; [0254] To 5-(l -benzenesulfonyl-5-chloro-lH-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2- ylamine (599, 124.1 mg, 0.31 mmol, prepared as described in Example 29, Scheme 185) in ethanol (3.00 mL) and acetic acid (0.2 mL) were added 6-(2,2,2-trifluoro-ethoxy)-pyridine-3- carbaldehyde (603, 164.0 mg, 0.80 mmol) and silica supported cyanoborohydride (1.21 mmol/g, 0.700 g). The reaction was irradiated with microwave on 300 watts, 1000C for 150 minutes. To the reaction was added a solution of potassium hydroxide (9.0 M in water, 1.0 mL). The reaction was irradiated with microwave on 300 watts, 100 0C for 10 minutes. The reaction was poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give the desired compound (P-0409, 10.6 mg, 7.6%). MS ESI) [M+H+]+ = 448.4.

With the rapid development of chemical substances, we look forward to future research findings about 159981-19-8.

Reference:
Patent; PLEXXIKON, INC.; WO2008/63888; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 18437-58-6, Adding some certain compound to certain chemical reactions, such as: 18437-58-6, name is 4-Amino-2-picoline,molecular formula is C6H8N2, 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 18437-58-6.

Et3N (275 mu, 1.983 mmol) was added to a mixture of intermediate 1-49 (290 mg, 0.693 mmol), Pd(OAc)2 (3 mg, 0.013 mmol), dppf (14 mg, 0.026 mmol), 4-amino-2-methylpyridine (71 mg, 0.661 mmol) in 1,4-dioxane (30 mL) was stirred under CO atmosphere (6 atm) at 90 C for 18h. The mixture was diluted with sat. sol. NaHCO3 and extracted with EtOAc. The organic layer was separated, dried (MgS04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in heptane 0/100 to 90/10). The desired fractions were collected and the solvents concentrated in vacuo. The product was triturated with pentane to yield final compound Co. No. 84 (135 mg, 45%). 1H NMR (300 MHz, CDCl3) delta ppm 1.76 (d, J=6.5 Hz, 3 H) 2.53 (s, 3 H) 3.99 (dd, J=12.9, 7.6 Hz, 1 H) 4.26 (dd, J=12.9, 4.3 Hz, 1 H) 4.75 – 4.90 (m, 1 H) 6.63 (t, J=72.7 Hz, 1 H) 7.22 – 7.29 (m, 1 H) 7.33 (s, 1 H) 7.47 (d, J=5.6 Hz, 1 H) 7.50 (s, 1 H) 7.61 (d, J=8.7 Hz, 1 H) 8.32 (s, 1 H) 8.36 (d, J=5.6 Hz, 1 H) 12.08 (br. s., 1 H).

According to the analysis of related databases, 18437-58-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ALONSO-DE DIEGO, Sergio-Alvar; VAN GOOL, Michiel, Luc, Maria; DELGADO-GONZALEZ, Oscar; ANDRES-GIL, Jose, Ignacio; TRABANCO-SUAREZ, Andres, Avelino; (183 pag.)WO2016/16380; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 127838-58-8, 4-(Hydroxymethyl)pyridin-2(1H)-one, 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, name: 4-(Hydroxymethyl)pyridin-2(1H)-one, blongs to pyridine-derivatives compound. name: 4-(Hydroxymethyl)pyridin-2(1H)-one

To a suspension of 4-(hydroxymethyl)-2(1 /-/)-pyridinone (0.98 g, 7.9 mmol) and DMF (10 ml_) was added imidazole (0.64 g, 9.45 mmol) and ferf-butyldimethylsilyl chloride (1.25 g, 8.26 mmol), and the mixture was stirred at ambient temperature under a nitrogen atmosphere for 18 h. The mixture was poured into water (30 ml_), and stirred for 30 min. The solid was filtered, rinsed with water, and air-dried to provide 4-({[(1 ,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-2(1 /-/)-pyridinone as an off-white solid (1.64 g, 88%): 1H NMR (400 MHz, DMSOd6) delta ppm 1 1.34 (br s, 1 H), 7.26 (d, J = 6.6 Hz, 1 H), 6.21 (s, 1 H), 6.01 (dd, J = 6.6, 1.5 Hz, 1 H), 4.5 (s, 2H), 0.88 (s, 9H), 0.05 (s, 6H); EI-LCMS m/z 241 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,127838-58-8, 4-(Hydroxymethyl)pyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/76387; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 61337-89-1, 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. 61337-89-1, name is 2-(4-Methyl-2-phenyl-1-piperazinyl)-3-pyridinemethanol, molecular formula is C17H21N3O, 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 3 Preparation of mirtazapine (I) from 1-(3-hydroxymethylpyridyl-2)-2-phenyl-4-methylpiperazine 100 ml of concentrated sulfuric acid was cooled to about 15 C. 50 grams (0.18 mole) of 1-(3-hydroxymethylpyridyl-2)-2-phenyl-4-methylpiperazine was added slowly to the sulfuric acid, and the temperature was maintained below 20 C. The temperature was then raised to 30 C., and the reaction mixture was stirred for 12 hours maintaining the temperature between 25 C. to 30 C. The reaction mass was then quenched in 1 liter of ice cold water. The pH of the reaction mixture was adjusted to about 10-11 using 20% to 25% aqueous ammonia solution while maintaining the temperature below 30 C. 500 ml of ethylacetate was added to the reaction mixture and stirred for about 15 minutes at 30 C. The layers were separated, and the aqueous layer was back extracted with 100 ml of ethylacetate. All the ethylacetate extracts were combined together and heated to reflux under stirring. 5 grams of activated charcoal was added, and the reaction mixture was stirred under reflux temperature for 30 minutes. The reaction mixture was filtered hot over a hyflo bed. 1.6 ml of water was added to the clear filtrate and heated to about 50 C. The reaction mass was stirred at 50 C. for 30 minutes and then concentrated under vacuum to keep about 100 ml of ethylacetate in the reaction mixture. 150 ml of isopropyl ether was added to the reaction mass and heated to reflux. 5 grams of activated carbon was added, and the reaction mixture was stirred under reflux for 30 minutes. The reaction mixture was filtered hot over a hyflo bed. The clear filtrate was cooled under stirring to about 30 C. and further chilled to about 5 C. The reaction mass was stirred at 5 C. to 10 C. for 1 hour. The resulting solid crystals were filtered and washed with 25 ml of chilled isopropyl ether. The product obtained was suck dried for 30 minutes and then dried at 65 C. under vacuum to get 40 grams of mirtazapine having HPLC purity of more than 99.8%.

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 61337-89-1, 2-(4-Methyl-2-phenyl-1-piperazinyl)-3-pyridinemethanol.

Reference:
Patent; WATSON PHARMA PRIVATE LIMITED; US2011/201804; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 7418-66-8, Adding some certain compound to certain chemical reactions, such as: 7418-66-8, name is 4-Aminonicotinamide,molecular formula is C6H7N3O, 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 7418-66-8.

To a stirred solution of 4-aminopyridine-3-carboxamide (500 mg, 3.65 mmol), 4-tert-butoxy-4-oxo-butanoic acid (762 mg, 4.38 mmol), TEA (1 mL, 7.29 mmol) in DMF (10 mL), 50%T3P solution in EtOAc (3.5 mL, 5.5 mmol) was added at RT and stirred for 12 h (TLCindicated complete consumption of starting material). The reaction mixture was quenchedwith water (50 mL) and extracted with DCM (2 x 35 mL). The combined organic extractswere washed with brine (30 mL), dried over Na2S04, concentrated under reduced pressure togive the crude product which was purified by column chromatography (100-200 silica gel, 20g, 10% MeOH-10% NH40H-DCM) to afford tert-butyl4-[(3-carbamoyl-4-pyridyl)amino]-4-oxo-butanoate (500 mg, 47%) as a yellow solid.1H NMR [400 MHz, CDCh]: J 11.74 (s, 1H), 9.07 (s, 1H), 8.69 (d, J = 5.2 Hz, 1H), 8.52 (d,J = 5.2 Hz, 1H), 7.11 (brs, 1H), 5.83 (brs, 1H), 2.75-2.70 (m, 2H), 2.68-2.63 (m, 2H), 1.44 (s,9H). LCMS (ESI+): m/z: 316.59 [M+Nat.

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. 7418-66-8, 4-Aminonicotinamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 63636-89-5, 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. 63636-89-5, name is Pyridine-2-sulfonamide, molecular formula is C5H6N2O2S, 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 6 N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminothioxomethyl]-2-pyridinesulfonamide A mixture of 1.58 g of 2-pyridinesulfonamide, 2.04 g of 4,6-dimethoxy-2-isothiocyanato-1,3,5-triazine and 1.5 g of anhydrous potassium carbonate is stirred in 75 ml of acetone for 60 hours at ambient temperature. The reaction mixture is then poured into 500 ml of cold water, acidified with hydrochloric acid and the precipitated product removed by filtration.

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 63636-89-5, Pyridine-2-sulfonamide.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4435206; (1984); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89937-77-9, 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 89937-77-9, name is Methyl 1,2-dihydro-2-oxopyridine-4-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Step 1 4-Hydroxymethyl-1H-pyridin-2-one 2-Oxo-1,2-dihydropyridine-4-carboxylic acid methyl ester (1.8 g, 12.2 mmol), prepared as described in J. Org. Chem., 26, 428 (1961), was suspended in THF (100 ml). A small amount of DMF was added to help increase solubility. LiBH4 (61 mmol) was added and the reaction was stirred for 18 hours at room temperature. MeOH and H2O are added to quench the reaction. The reaction is then concentrated to yield a yellow oil. Flash chromatography (5% MeOH/CHCl3 to 20% MeOH/CHCl3) yielded 4-hydroxymethyl-1H-pyridin-2-one as a white solid. 1H NMR (400 MHz, CD3OD) delta 7.38-7.36 (1H,d); 6.56 (s, 1H); 6.37-6.36 (d, 1H); 4.50 s, 2H).

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 89937-77-9, Methyl 1,2-dihydro-2-oxopyridine-4-carboxylate.

Reference:
Patent; Defeo-Jones, Deborah; Jones, Raymond E.; Oliff, Allen I.; US2003/220241; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem