Pyridine-derivatives

Electric Literature of 58481-11-1, 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. 58481-11-1, name is Methyl 2-chloroisonicotinate, molecular formula is C7H6ClNO2, 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.

1. Synthesis of methyl 2-(thiazol-2-ylamino)isonicotinate A suspension of methyl 2-chloroisonicotinate (15.0 g, 87.42 mmol), 2-aminothiazole (10.50 g, 104.9 mmol), sodium carbonate (12.97 g, 122.4 mmol, 1.4 eq) and XANTPHOS (0.607 g, 1.049 mmol, 0.012 eq) in toluene (300 mL, bubbled with argon for 5 minutes) was bubbled again with argon for 5 additional minutes. Tris(dibenzylideneacetone)dipalladium (0) (0.320 g, 0.349 mmol, 0.004 eq) was then added to the suspension which was heated at 100° C. for 5 days. The mixture was cooled down to RT and filtered. The resulting solid was suspended in water and stirred for 1 hour. After filtration, the resulting solid was dried under vacuum overnight and afforded the title material (14.17, 69percent) as a solid. 1H NMR (400 MHz, DMSO-d6) delta (ppm): 3.90 (3H, s), 7.07 (1H, d, J=3.54), 7.32 (1H, dd, J=5.31, 1.26 Hz), 7.43 (1H, d, J=3.79 Hz), 7.61 (1H, s), 8.48 (1H, d, J=4.55 Hz), 11.56 (1H, s). LC/MS (M+H)+: 236. HPLC ret. time (Condition A): 1.182 min.

According to the analysis of related databases, 58481-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; US2010/48581; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1214334-70-9, 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 1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

5-bromo-6-methoxypicolinic acid (5 g, 22 mmol) was dissolved in DMF (50 mL) and cooled to 0C under argon. DIPEA (7.66 mL, 44 mmol), ammonium chloride (1.77 g, 33 mmol) and HATU (12.6 g, 33 mmol) were added and the mixture was warmed to room temperature and stirred overnight. Water (50 mL) was added and the solid precipitate 5-bromo-6-methoxypicolinamide was collected by filtration(4.21 g, 83%). ?H NMR (DMSO, 400 MHz): 8.14 (d, 1H), 8.04 (br s, 1H), 7.71 (br s, 1H), 7.48 (d, 1H), 4.00 (s, 3H). LCMS (basic, 3.1 mm): RT 1.64 mi [MHj+ 232.9, purity 83%.

According to the analysis of related databases, 1214334-70-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FORUM PHARMCEUTICALS INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; MCRINER, Andrew, J.; (451 pag.)WO2016/201168; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 18088-01-2 , The common heterocyclic compound, 18088-01-2, name is (2,6-Dimethylpyridin-4-yl)methanol, molecular formula is C8H11NO, 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 2,6-dimethylpyridylmethyl alcohol (5.0 g, 36.4 mmol) and NEt3 (12.7 mL, 91.1 mmol) in DCM (100 mL) was added methanesulfonyl chloride (5.62 mL, 72.9 mmol). The mixture was stirred for one hour at r.t. and then concentrated in vacuo. The residue was dissolved in EtOAc (100 mL), washed with sat aq NaHCO3 solution (50 mL), brine (50 mL), dried (MgSO4) and concentrated in vacuo to give a mixture of (2,6- dimethylpyridin-4-yl)methyl methanesulfonate and 4-(chloromethyl)-2, 6-dimethylpyridine (4.86 g). A portion (2.0 g) of this mixture was dissolved in DMF (4 mL), JV-ethylamine (1.79 mL, 32.2 mmol) added and the mixture heated in a Biotage Initiator microwave at 170 0C for 20 minutes at normal absorption. The reaction mixture was concentrated in vacuo and the residue purified by reverse phase chromatography to give (4-methyl-JV- ethylamine)-2, 6-dimethylpyridine (702 mg, 28%) as a colourless oil.

The synthetic route of 18088-01-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOVITRUM AB (publ); WO2009/147211; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 876919-08-3, Adding some certain compound to certain chemical reactions, such as: 876919-08-3, name is Methyl 3-fluoroisonicotinate,molecular formula is C7H6FNO2, 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 876919-08-3.

To a suspension ofPreparation 54A (480 mg, 2.7 mmol) in DMA (5 mL) was added methyl3-fluoroisonicotinate at rt. The reaction mixture was stirred at 170 oc for 1 h in a microwave. Concentration in vacuo followed by purification by silica gelchromatography gave 395 mg (47%) of the title compound as a yellow gum. [M+H]calc’d for C1sH19FNzOz, 315; found 315.

According to the analysis of related databases, 876919-08-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; QUANTICEL PHARMACEUTICALS, INC.; CHEN, Young, K.; KANOUNI, Toufike; NIE, Zhe; STAFFORD, Jeffrey, Alan; VEAL, James, Marvin; WALLACE, Michael, Brennan; WO2014/100818; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 115473-15-9, 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. 115473-15-9, name is 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride, molecular formula is C7H10ClNOS, 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-5: Purification of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]-pyridin-2-one- hydrochloride A mixture of dichloromethane (425 ml), methanol (75 ml) and 5,6,7,7a-tetrahydro-4H- thieno[3,2-c]-pyridin-2-one-hydrochloride (100 grams) was heated to reflux. The reaction mixture was stirred for 30 minutes and cooled to 25-30C and further stirred for 1 hour. The solid obtained was filtered, washed with dichloromethane and dried to get the title compound.Yield: 88 grams; Assay: 98.5%

According to the analysis of related databases, 115473-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; ELEVATHINGAL NICHOLAS, Madhu; RAMA SUBBA REDDY, Karamala; WO2011/92720; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13362-28-2, 2-Amino-4-pyridinecarboxylic 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, Computed Properties of C6H6N2O2, blongs to pyridine-derivatives compound. Computed Properties of C6H6N2O2

300 mg of 2-aminoisonicotinic acid (II-1) (2.172 mmol, 1 eq) was weighed into a 25 mL round bottom flask.Add 4 mL of methylene chloride and add 335 muL of anhydrous DMF (4.344 mmol, 2 eq).After stirring, 370 muL of oxalyl chloride (4.344 mmol, 2 eq) was added dropwise, and the mixture was stirred at room temperature for 30 minutes,The solution is light pink. Followed by the addition of p-methoxyaniline (2.606 mmol, 1.2 eq)And stirred at room temperature for 1.5 hours. The solution was light brown and white smoke was generated.525 mul of pyridine (6.516 mmol, 3 eq) and 2 mL of dichloromethane were added to the ice bath,Followed by stirring at room temperature for 30 minutes, the solution turned black and then turned orange, with bubbles generated.The solvent was dried to give a pale red solid which was added 5 mL of ethanol and 655 muL of ethylenediamine(9.774 mmol, 4.5 eq), heated and refluxed for 30 minutes. TLC detection reaction is completed,Stop heating, cooling directly after filtration, water and ether several times to clean the filter cake, infrared light drying,To give 399 mg of a pale yellow solid,2-amino-N- (4-methoxyphenyl) isonicotinamide (III-1) in a yield of 75.5%.

The synthetic route of 13362-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Sun Hongbin; Xin Tao; Wen Xiaoan; Wu Yizhou; Yuan Haoliang; (14 pag.)CN106632021; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 230301-11-8 , The common heterocyclic compound, 230301-11-8, name is tert-Butyl 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate, molecular formula is C11H17N3O2, 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 209.2: To a solution of 1,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert- butyl ester (279mg) in MeCN (10ml) was added Cs2CO3 (407mg) followed by benzyl bromoacetate (0.2ml). The resulting white suspension was stirred at RT for 48h, diluted with EA and washed with water and brine. The aq. phases were extracted with EA. The combined org. layers were dried (MgS04), filtered off and evaporated to dryness. The residue was purified by CC (Biotage, SNAP 25g cartridge, DCM/MeOH 97/3 for 10CV) to afford 371 mg of oil. The oil was purified by preparative chiral HPLC (I) to afford the two regioisomers, both as mixture of benzyl and ethyl ester that formed during the evaporation of the fractions after HPLC purification: Step 209.3: The Boc protecting group of 1-benzyloxycarbonylmethyl-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester was cleaved using a method analogous to that of Example 16 step 16.4 to give (4,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-1-yl)-acetic acid benzyl ester. Step 209.4: To a solution of (4,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-1-yl)-acetic acid benzyl ester (176mg) in MeOH was added formaldehyde (36.5% in water, 0.052ml_) followed by NaBH3CN (29mg) and AcOH (0.5ml_). The reaction mixture was stirred at RT overnight. DCM was added and the mixture was washed with sat. NaHCO3. The aq. layer was extracted with DCM, the combined org. layers were dried (MgS04), filtered off and evaporated to dryness. The residue was purified by CC (Biotage, SNAP 10g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8/2; gradient in %B: 25 for 3CV, 25 to 50 over 2CV, 50 for 5CV, 50 to 100 over 3CV, 100 for 2CV) to afford (5-methyl-4,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-1-yl)-acetic acid benzyl ester (39mg, yellow oil). (5-Methyl-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-2-yl)-acetic acid benzyl ester (1 1 1 mg, colourless oil). LC-MS (B): tR = 0.54min; [M+H]+: 286.16. 1H-NMR (CDCl3): 7.40-7.33 (m, 5H); 7.18 (s, 1 H); 5.21 (s, 2H); 4.89 (s, 2H); 3.50 (s, 2H); 2.86 (t, 2H, 6.0Hz); 2.76 (t, 2H, 5.5Hz); 2.49 (s, 3H). Roesy signal seen between CH2 at 4.89ppm and CH at 7.18ppm. (5-Methyl-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1 -yl)-acetic acid benzyl ester (45mg, pale yellow solid). LC-MS (B): tR = 0.54min; [M+H]+: 286.16. 1H-NMR (CDCl3): 7.40-7.33 (m, 6H); 5.21 (s, 2H); 4.85 (s, 2H); 3.47 (s, 2H); 2.75 (t, 2H, 6.0Hz); 2.67 (t, 2H, 5.5Hz); 2.49 (s, 3H). Roesy signal seen between CH2 at 4.85ppm and CH2 at 2.67ppm. Step 215.2: The final compound was prepared using a method analogous to that of Example 14 step 14.2, (5-methyl-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-2-yl)-acetic acid benzyl ester replacing intermediate 14.1 and using MeOH instead of MeOH/AcOH. LC-MS (B): tR = 0.17min; [M+H]+: 196.29.

The synthetic route of 230301-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CAROFF, Eva; KELLER, Marcel; KIMMERLIN, Thierry; MEYER, Emmanuel; WO2013/114332; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 897732-75-1, 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. 897732-75-1, name is 2-Methyl-6-(methylsulfonyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

EXAMPLE 55; 3-(l-(5-Ethylpyrimidin-2-yl)piperidin-4-yl)-N-(2-methyl-6-(methylsulfonyl) pyridin-3-yl)-[l,2,4]triazolo[4,3-b]pyridazin-8-amineStep 1: 3,6-Dichloro-N-(2-methyl-6-(methylsulfonyl)pyridin-3-yl)pyridazin-4- amine [0394] A 100-mL round-bottom flask was charged with a solution of 2-methyl- 6-(methylsulfonyl)pyridin-3-amine (500 mg, 2.69 mmol) in tetrahydrofuran (50 mL), sodium hydride (269 mg, 11.2 mmol), and 3,4,6-trichloropyridazine (1 g, 5.49 mmol). The resulting solution was stirred for 16 hrs at room temperature. The reaction was then quenched with brine (50 mL), extracted with ethyl acetate (4×50 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give a residue. This residue was purified by a silica gel column chromatography eluted with dichloromethane/ethyl acetate (2/1) affording 3,6-dichloro-N-(2-methyl-6-(methylsulfonyl)pyridin-3-yl)pyridazin-4-amine as pale yellow solid (0.75 g, 84%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,897732-75-1, 2-Methyl-6-(methylsulfonyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; KALYPSYS, INC.; KAHRAMAN, Mehmet; SMITH, Nicholas, D.; BONNEFOUS, Celine; NOBLE, Stewart, A.; PAYNE, Joseph, E.; WO2010/88518; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 84703-18-4, Adding some certain compound to certain chemical reactions, such as: 84703-18-4, name is 5-Bromo-2-chloro-6-methylnicotinonitrile,molecular formula is C7H4BrClN2, 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 84703-18-4.

General procedure: A mixture of 10a-10k (1 mmol), methyl thioglycolate (159 mg,1.5 mmol) and Et3N (152 mg, 1.5 mmol) in 10 mL of methanol was stirred at 80 C for 6-8 h. Methanol was removed under vacuum.The residuewas purified by column chromatography to provide thetitle compound.

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. 84703-18-4, 5-Bromo-2-chloro-6-methylnicotinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhao, Yan; Li, Min; Li, Bowen; Zhang, Shun; Su, Aoze; Xing, Yongning; Ge, Zemei; Li, Runtao; Yang, Baoxue; European Journal of Medicinal Chemistry; vol. 172; (2019); p. 131 – 142;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1180132-17-5, 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. 1180132-17-5, name is 5-((4-Ethylpiperazin-1-yl)methyl)pyridin-2-amine, molecular formula is C12H20N4, 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.

General procedure: To a solution of 5a (0.10 g, 0.33 mmol) and 9a (0.07 g, 0.33 mmol) in 1,4-dioxane (2 mL), were added Cs2CO3 (0.21 g, 0.65 mmol), Pd2(dba)3 (0.03 g, 0.03 mmol) and XantPhos (0.03 g, 0.06 mmol). The mixture was heated to 120 C for 60 min with microwave, then cooled to room temperature, diluted with water (10 mL), and extracted with DCM (40 mL × 3). The combined organic layers were washed with water (40 mL) and brine (40 mL), dried over anhydrous Na2SO4, concentrated under vacuum, and purified by silica gel column chromatography (DCM / MeOH = 20:1) to give compound 10a (0.02 g, 12.40%) as a yellow solid.

According to the analysis of related databases, 1180132-17-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Yan; Liu, Wen-Jian; Yin, Lei; Li, Heng; Chen, Zhen-Hua; Zhu, Dian-Xi; Song, Xiu-Qing; Cheng, Zhen-Zhen; Song, Peng; Wang, Zhan; Li, Zhi-Gang; Bioorganic and Medicinal Chemistry Letters; vol. 28; 5; (2018); p. 974 – 978;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem