Category: pyridine-derivatives

Electric Literature of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, 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.

To a stirred solution of (2S)-2-methylpiperazine (0.30 g, 2.1 mmol) in DMA (6 mL), 6-chloropyridine-3-carbonitrile (0.29 g, 2.3 mmol) and K2C03 were added. The resultantreaction mixture was heated to 60 C for 2 h (TLC indicated complete consumption ofstarting material). The reaction mixture was diluted with cold water (20 mL) and extractedwith EtOAc (3 x 25 mL). The combined organic extracts were washed with cold water (20mL) and brine (2 x 20 mL). The organic layer was separated, dried over Na2S04 andconcentrated under reduced pressure to give the crude residue which was purified by columnchromatography (100-200 silica gel, 10 g, 10% MeOH-DCM) to furnish 6-[(3S)-3-methylpiperazin-1-yl]pyridine-3-carbonitrile (0.29 g, 67%) as an off-white solid.LCMS: m/z: 203.4 [M+Ht.

According to the analysis of related databases, 33252-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); 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. 58553-48-3, name is 5-(Hydroxymethyl)picolinonitrile, molecular formula is C7H6N2O, 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. Formula: C7H6N2O

Example 3A; 5-Formyl-2-pyridinecarbonitrile 1.04 g (8. 2 mmol) oxalylchloride are dissolved in 8 ml dichloromethane. At-78C, 1.28 g (16.4 mmol) dimethylsulfoxide are added dropwise. The solution is stirred at-78C for 20 minutes, then 1 g (7.46 mmol) of the compound of Example 2A, dissolved in 7 ml dichloromethane, is added, and stirring at-78C is continued for another 2 hours. 3.4 g (33.6 mmol) triethylamine are then added dropwise, and after warming up to room temperature, the mixture is purified by column chromatography (silica, eluent: cyclohexane to cyclohexane/ethyl acetate 2: 1). Yield: 0.76 g (77% of th.) Mp.: 80-82C HPLC (method 4): Rt = 2.13 min MS (ESIpos): m/z = 133 (M+H) + ‘H-NMR (400 MHz, DMSO-d6) : 8 = 10. 18 (s, 1H), 9.21 (m, 1H), 8.49 (m, 1H), 8.27 (m, 1H) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 58553-48-3.

Reference:
Patent; BAYER HEALTHCARE AG; WO2005/82863; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1003711-43-0, 2-Bromo-5-hydroxy-3-methylpyridine, 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, Safety of 2-Bromo-5-hydroxy-3-methylpyridine, blongs to pyridine-derivatives compound. Safety of 2-Bromo-5-hydroxy-3-methylpyridine

0.49 g (6.82 mmoi) cyclopropane methanol in 10 mL THF are charged with 0.42 g (11.4 mmoi) NaH and the reaction mixture is stirred at r.t. for 20 min. Then 1.00 g (5.68 mmoi) 5-bromo-2-fluoropyridine are added and the mixture is stirred at r.t. over night. The reaction is quenched by the addition of water and extracted with EtOAc. The organic layers are combined, dried over MgS04l filtered and the solvent is removed in vacuo. The crude product is purified by HPLC (MeOH/H20/FA). CgH-ioBrNO (M= 228.1 g/mol) ESI-MS: 228/229 [M+H]+ Rt (HPLC):1.14 min (method C) The following compounds are prepared analogously to example XXV.1 ; For example XXV.4 the reaction conditions are 50 C for 4 h. For examples XXV.10 – XXV.13 and XXV.19 – XXV.21 the reaction time is 2 h. For example XXV.9 no solvent is used and the reaction temperature is 95 C. For the examples XXV.4, XXV.10 – XXV.12, XXV.15 – XXV.16 and XXV.19 – XXV.21 the reaction is done in DMF. For example XXV.18 the reaction is done in DMSO at 100 C. For example XXV.21 toluene is used as solvent and the reaction conditions are 50 C for 1 h. For example XXV.22 methyltetrahydrofurane is used as solvent at 0 C for the deprotonation and 50 C for the substitution..

The synthetic route of 1003711-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; WO2014/114578; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 112110-07-3, 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.112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.

1-(((Benzyloxy)carbonyl)amino) cyclopropane-1-carboxylic acid (50 mg, 0.21 mmol), 5-(trifluoromethyl)pyridin-3-amine (104 mg, 0.64 mmol), and DIPEA (111 muL, 0.64 mmol) were dissolved in DMF (1 mL), and then HATU (97 mg, 0.26 mmol) was added thereto, followed by stirring at room temperature overnight. A saturated aqueous sodium hydrogen carbonate solution was added to a reaction liquid, the mixture was stirred for a while, and then extraction was performed with ethyl acetate. A separated organic layer was washed with a saturated saline solution and dried over anhydrous sodium sulfate, an insoluble substance was filtered, and then a solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) (concentration gradient: 40% to 60%) to obtain a crude product (white powders, 126 mg) of benzyl (1-((5-(trifluoromethyl)pyridin-3-yl)carbamoyl)cyclopropyl)carbamate.

The chemical industry reduces the impact on the environment during synthesis 112110-07-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; Kinki University; TANAKA Hiroto; OOI Isao; HAYASHIDA Kohei; OGAWA Toru; KAWABATA Atsufumi; (64 pag.)EP3572403; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 727356-19-6, name is 2-Bromo-6-(chloromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H5BrClN

Step 3; Preparation of 3-oxopiperazine-1-carboxyimidothionic acid 6-bromopyridin-2-ylmethyl ester 2-Bromo-6-chloromethylpyridine (1.50 g, 7.26 mmol) obtained in Step 1 was dissolved in ethanol (15 ml) and 3-oxopiperazine-1-carbothionic acid amide (1.16 g, 7.29 mmol) obtained in Step 2 was added, and the mixture was heated to reflux for 2 hours. After the reaction solution was cooled to room temperature, the solution obtained by vacuum concentration was neutralized with a saturated aqueous sodium bicarbonate, and the precipitated solid was separated by filtration, washed with water and the title compound (1.67 g, 70%) was obtained.

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, 727356-19-6, 2-Bromo-6-(chloromethyl)pyridine.

Reference:
Patent; JAPAN TOBACCO INC.; US2006/205731; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 3222-56-8, Adding some certain compound to certain chemical reactions, such as: 3222-56-8, name is 2-Methylnicotinic acid,molecular formula is C7H7NO2, 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 3222-56-8.

To a solution of acid 2-methylpyridin-3-carboxylic (0.40 g, 2.90 mmol, 1 eq) in DMF dry (4.0 mL), ammonium chloride (0.93 g, 17.50 mmol, 6 eq), HOBt (0.57 g, 4.20 mmol, 1.44 eq), EDCI (0.81 g, 4.20 mmol, 1.44 eq) and N-methylmorpholine (0.46 mL, 4.20 mmol, 1.44 eq) were subsequently added. The reaction was stirred at room temperature, under nitrogen for 2.5 h. Evaporation of the solvent gave a residue which was purified by column chromatography (neutral alumine oxide, Brockmann grade III) using EtOAc as eluant to give 9 as white solid after crystallization with EtOAc (0.27 g, 69%). Mp. 163-166 C. 1H NMR (300 MHz, CD3OD) delta 8.45 (dd, J = 4.9/1.8 Hz, 1-H), 7.83 (dd, J = 7.6/1.5 Hz, 1-H), 7.30 (dd, J = 7.6/4.9 Hz, 1-H), 2.61 (s, 3-H); 13C NMR (75 MHz, CD3OD) delta 172.0, 155.4, 149.2, 135.7, 132.2, 121.2, 21.2; GC-MS m/z 136 (M)+; IR (KBr) 2768, 2389, 1926, 1692, 1448, 1365 cm-1. Anal. Calcd for C7H8N2O: C, 61.75; H, 5.92; N, 20.58. Found: C, 61.91; H, 6.20; N, 20.10.

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. 3222-56-8, 2-Methylnicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Galli, Ubaldina; Mesenzani, Ornella; Coppo, Camilla; Sorba, Giovanni; Canonico, Pier Luigi; Tron, Gian Cesare; Genazzani, Armando A.; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 58 – 66,9;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 42182-25-2, 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. 42182-25-2, name is 1-(2-Aminopyridin-4-yl)ethanone, molecular formula is C7H8N2O, 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.

To a mixture of (36) (168 mg, 1.234 mmol) in MeOH (10 mL), under nitrogen at 0 C., was added sodium borohydride (46.7 mg, 1.234 mmol). The reaction mixture was stirred at RT for 2 hr, and the volatiles were removed under reduced pressure. The residue was taken up into EtOAc (25 mL), and extracted with saturated aq NaHCO3 solution (30 mL). The aqueous layer was back extracted with EtOAc (2*20 mL), and the combined organic extracts were washed with brine (30 mL), dried and the solvents removed in vacuo to give 1-(2-aminopyridin-4-yl)ethanol (37) (77 mg, 45%) as a yellow oil: m/z 139 (M+H)+ (ES+).

According to the analysis of related databases, 42182-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Charron, Catherine Elisabeth; Fenton, Robert; Crowe, Scott; Ito, Kazuhiro; Strong, Peter; Rapeport, William Garth; Ray, Keith; US2012/244120; (2012); 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.112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.Quality Control of 5-(Trifluoromethyl)pyridin-3-amine

Step 5: 4-Methyl-3-(9H-pyrimido[4, 5-bJindol- 7-yl)-N-[5-(trifluoromethyl)pyridin-3-yl]benzamideTo a vial was added 4-methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)benzoic acid (15.2 mg, 0.0501 mmol), DMF (0.32 mL), and AWN’N’-tetramethyl-O-(7-azabenzotriazol-l-yl)uronium hexafluorophosphate (22.9 mg, 0.0601 mmol). This mixture was stirred 15 min at RT. To the mixture was then added 5-(trifluoromethyl)pyridin-3-amine (10.6 mg, 0.0651 mmol. The resulting mixture was stirred at 70 0C for 18 h. LCMS indicated complete consumption of the activated ester (M+H 422) and showed product (M+H 448). The product was isolated by prep HPLC/MS using a 19 mm x 100 mm C18 column; 28%CH3CN-H2O (0.1% TFA), 1 min, to 48% at 6 min; 30 mL/min. The HPLC fractions containing the product were freeze dried to yield a light yellow solid, 5.6 mg, 20% yield. FMR showed that it was the mono TFA salt; and contained some residual PF6. 1H NMR (DMSOd6) delta 13.29 (s, IH, NH); 10.76 (s, IH, amide NH); 9.72 (s, IH); 9.22 (s, IH); 9.20 (s, IH); 8.69 (s, IH); 8.62 (s, IH); 8.44 (d, IH); 7.98 (m, 2H); 7.66 (s, IH); 7.56 (d, IH); 7.53 (d, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; INCYTE CORPORATION; WO2008/79965; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 117846-58-9, 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.117846-58-9, name is 2,6-Dibromo-3,5-dimethylpyridine, molecular formula is C7H7Br2N, molecular weight is 264.95, as common compound, the synthetic route is as follows.

To a solution of 2,6-dibromo-3,5-dimethylpyridine (1.0 g, 3.77 mmol) in toluene (30 mL) was added n-BuLi (1.5 mL, 3.77 mmol) dropwise at -78 C. After 1 h, DMF (358 mg, 4.9 mmol) was added to the mixture for additional lh. The mixture was adjusted to pH = 34 using HC1 and extracted with EtOAc (50 mL x 3) and the organic layers were concentrated and purified by chromatography (silica, ethyl acetate/petroleum ether =1/10) to afford 6-bromo-3,5- dimethylpicolinaldehyde (242 mg, 1.13 mmol, 30%) as a white solid. ESI-MS (EI, m/z): 214.1 [M+H].

Statistics shows that 117846-58-9 is playing an increasingly important role. we look forward to future research findings about 2,6-Dibromo-3,5-dimethylpyridine.

Reference:
Patent; NAVITOR PHARMACEUTICALS, INC.; O’NEILL, David John; SAIAH, Eddine; KANG, Seong Woo Anthony; BREARLEY, Andrew; BENTLEY, Jonathan; (565 pag.)WO2018/89433; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, Product Details of 89415-54-3, blongs to pyridine-derivatives compound. Product Details of 89415-54-3

In a flask were combined 2-methylpropanamide (Aldrich, cat144436: 285 mg, 3.28 mmol), THF (2 mL) and triethyloxonium tetrafluoroborate (Aldrich, cat90520: 0.617 g, 3.25 mmol). The reaction mixture was allowed to stir at room temperature for 2 hours. The solvent was removed under reduced pressure and the residue was dissolved in ethanol (1.9 mL). To this residue was added a suspension of 5-bromo-N2-methylpyridine-2,3-diamine (200 mg, 0.99 mmol) [Combi-Blocks cat AN-3965] in ethanol (6.7 mL). The mixture was then stirred at 80 C. for 1 hour. After the crude reaction mixture had cooled to room temperature the solvent was removed under reduced pressure. The residue was purified by flash chromatography on a silica gel column eluting with 0 to 20% MeOH/DCM to give the desired product (48 mg, 19% yield). LC-MS calculated for C10H13BrN3 (M+H)+: m/z=254.0. found 254.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Konkol, Leah C.; Lajkiewicz, Neil; Lu, Liang; Xu, Meizhong; Yao, Wenqing; Yu, Zhiyong; Zhang, Colin; He, Chunhong; (107 pag.)US2016/9712; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem