Pyridine-derivatives

Related Products of 780800-73-9, 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. 780800-73-9, name is (3-Isopropylpyridin-2-yl)methanol. A new synthetic method of this compound is introduced below.

To a vigorously stirred solution of (3-isopropyl-pyridin-2-yl)-methanol (26 g, 170 mmol) in CH2Cl2 (575 mL) was added manganese(IV) oxide (105 g, 1.20 mol) under N2. The mixture was stirred for 18 h then filtered through a celite pad and concentrated in vacuo. Purification by column chromatography on silica gel (EtOAc/hexanes, 1:3) afforded 3-isopropyl-pyridine-2-carbaldehyde (15.65 g, 61%) as an orange oil. 1H NMR (CDCl3) delta 1.26 (d, 6H, J=7.0 Hz), 4.17 (sep, 1H, J=6.6 Hz) 7.45 (dd, 1H, J=7.9, 4.4 Hz), 7.84 (d, 1H, J=7.9 Hz), 8.56 (dd, 1H, J=4.4, 1.3 Hz), 10.2 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,780800-73-9, (3-Isopropylpyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Bridger, Gary; McEachern, Ernest J.; Skerlj, Renato; Schols, Dominique; US2004/209921; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1314353-68-8, 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. 1314353-68-8, name is 5-Cyclopropylpyridin-3-amine, molecular formula is C8H10N2, 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.

3-Amino-5-cyclopropylpyridine obtained in the above-described Step 1 (67 mg) and p-toluenesulfonic acid monohydrate (10 mg) were added to a solution of ethyl 5-chloro-3-(methylthio)-1,2,4-triazine-6-carboxylate (70 mg) in DMF (1 ml), and the reaction solution was stirred in a microwave reactor at 100C for 30 minutes. The reaction solution was diluted with ethyl acetate, and washed successively with an aqueous sodium bicarbonate solution, water, and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent: hexane/ethyl acetate) to obtain ethyl 5-(5-cyclopropylpyridin-3-ylamino)-3-(methylthio)-1,2,4-triazine-6-carboxylate as a white solid.

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 1314353-68-8, 5-Cyclopropylpyridin-3-amine.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; SAKAMOTO, Toshihiro; MITA, Takashi; SHIBATA, Kazuaki; OGINO, Yoshio; KOMATANI, Hideya; EP2762476; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13466-35-8 , The common heterocyclic compound, 13466-35-8, name is 3-Chloro-2-hydroxypyridine, molecular formula is C5H4ClNO, 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 500 ml four-necked flask equipped with a thermometer, mechanical stirring, and a reflux condenser was added 150 g of 1,2-dichloroethane, 26.0 g (0.2 mol) of 2-hydroxy-3-chloropyridine prepared in Example 3, 52.0 g (0.25 mole) of phosphorus pentachloride, stir the reaction at 60-65 C for 10 hours, then slowly pour the residue into 200 g of ice water, stir well, and then neutralize the pH value with a 40 wt% sodium hydroxide aqueous solution. 8. The layers were separated. The aqueous layer was 50g with 1,2-dichloroethane three times. The organic phases were combined, washed with 30g of saturated brine, and then dried with 5g of anhydrous sodium sulfate. The solvent was removed by rotary evaporation. 28.1 g of 2,3-dichloropyridine (I) with a yield of 94.9% and a gas phase purity of 99.9%.

The synthetic route of 13466-35-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Qi Yuxin; Sun Yulong; Zhang Mingfeng; Chang Renyi; Wang Tao; (10 pag.)CN110818622; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 53554-20-4 ,Some common heterocyclic compound, 53554-20-4, molecular formula is C6H4ClN3, 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.

38 (1.00g crude, max 4.30mmol), diethylzinc (1.0M in hexane, 7.81mmol, 7.8mL), and Pd2(PPh3)4 (150mg, 0.13mmol) were added to a microwave vial along with NMP (8mL). The vial was flushed with N2, sealed and heated using microwave irradiation at 100C for 30min. The contents of the vial were cooled to rt and washed with sat. aq. NaHCO3 (120mL), and H2O (120mL), dried over Na2SO4, and evaporated under vacuum. Purification by FC (heptane/EtOAc 80:20 to 50:50) afforded the product as brown solid (333mg, 53% over 2 steps). 1H NMR (CDCl3) delta 7.56 (d, J=8.5Hz, 1H), 6.34 (d, J=8.5Hz, 1H), 4.99 (b s, 2H), 2.86 (q, J=7.6Hz, 2H), 1.31 (t, J=7.6Hz, 3H). 13C NMR (CDCl3) delta 167.4, 159.8, 141.4, 118.5, 105.7, 96.6, 30.4, 13.5.

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. 53554-20-4, 6-Amino-2-chloronicotinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Petersen, Jette G.; S°rensen, Troels; Damgaard, Maria; Nielsen, Birgitte; Jensen, Anders A.; Balle, Thomas; Bergmann, Rikke; Fr°lund, Bente; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 404 – 416;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 4684-94-0, 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.4684-94-0, name is 6-Chloropicolinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.55, as common compound, the synthetic route is as follows.

6-Chloropyridine-2-carboxylic acid (1.20 g, 7.62 mmol) and ammonium chloride (0.81 g, 15.2 mmol) were dissolved in DMF (20 mL) and DIPEA (5.31 mL, 30.5 mmol), HONB (2.05 g, 11.4 mmol) and HBTU (4.33 g, 11.4 mmol) were added. The reaction mixture was stirred for 1 h and the solvents were removed in vacuo. The residue was partitioned between DCM (50 mL) and 1 M aq HCl (50 mL) and the aq fraction was extracted with DCM (2*25 mL). The combined organic fractions were washed with sat aq NaHCO3 (50 mL), brine (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was recrystallised from MeOH/water to give the title compound (1.12 g, 94%) as a white solid. LCMS (ES+): 157.4 [MH]+.

Statistics shows that 4684-94-0 is playing an increasingly important role. we look forward to future research findings about 6-Chloropicolinic acid.

Reference:
Patent; Proximagen Limited; Savory, Edward Daniel; Stewart, Allson; Cartey, Allison; Brown, Giles; Simpson, Iain; Oliver, Kathryn; Patient, Lee; Higginbottom, Michael; Cole, Andrew Graham; US2013/289020; (2013); 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. 58484-01-8, name is 3-Amino-2,6-dichloroisonicotinic acid, molecular formula is C6H4Cl2N2O2, 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. Product Details of 58484-01-8

Step 4 : Preparation of 6, 8-dichloro-2- [2- (3-chloro-pyridin -2-yl) -5-trifluoromethyl-2ff-pyrazol-3-yl] -pyrido [3, 4-d] [1, 3] oxazin-4-one; 5-Trifluoromethyl-2- (3-chloro-pyridin-2-yl) -2H-pyrazole-3- carboxylic acid chloride (example 2, step 3) (242 mg) was added to a mixture of 3-amino-2 , 6-dichloroisonicotinic acid (example 1, step 8) (190 mg) in acetonitrile (3 mL) . The mixture was stirred for 5 minutes at room temperature and triethylamine (220 muL) was added and stirred for 20 minutes, before a second portion of triethylamine (220 muL) was added. After the mixture was stirred for further 20 minutes at room temperature, methanesulfonyl chloride (70 muL) was added. After stirring for 2 hours at room temperature, the formed precipitate was filtered off, washed carefully with water and MTB-ether and dried in vacuum to afford 350 mg of the title compound of the formulaas a yellow solid. 1H-NMR (CDCl3, TMS) 6 (ppm) : 7.54-7.57 (2H, m) , 7.88 (IH, s), 8.01-8.04 (IH, m) , 8.56-8.58 (IH, m) .

With the rapid development of chemical substances, we look forward to future research findings about 58484-01-8.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/130021; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1020253-14-8, 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 1020253-14-8 as follows.

This compound (14 mg, 0.026 mmol, 26% yield) as a white solid was prepared in a fashion similar to that described for Example 116, here using 116a (42 mg, 0.101 mmol) and 6-chloro-5-fluoronicotinonitrile (24 mg, 0.151 mmol) as starting materials. LC/MS (ESI+) m/z = 538.1 [M+H]+. NMR (400 MHz, CHLOROFORM-d) delta ppm 8.66 (d, J = 2.54 Hz, 1H) 7.97 – 8.02 (m, 1H) 7.70 (dd, J = 7.14, 2.64 Hz, 1H) 7.58 – 7.65 (m, 1H) 7.1 1 (dd, J = 1 1.54, 8.61Hz, lH) 6.62 (d, J = 14.87 Hz, lH) 6.42 (d, J = 14.87 Hz, 1H) 4.58 – 4.92 (m,2H) 3.54 – 3.75 (m, 8 H) 2.10 (t, J = 8.31Hz, 1H) 1.41 (dd, J = 9.59, 5.87 Hz, 1H) 1.08 (t, J = 6.36 Hz, 1H). N peak was not observed.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1020253-14-8, its application will become more common.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; CHEN, Jian J.; FROHN, Michael J.; HARRINGTON, Paul E.; LOW, Jonathan D.; MA, Vu V.; NGUYEN, Thomas T.; PICKRELL, Alexander J.; REEVES, Corey; (122 pag.)WO2018/112086; (2018); 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. 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4-Bromo-2-chloro-5-methylpyridine

A mixture of 66 (0.35g, 1.02mmol), 4-bromo-2-chloro-5-methylpyridine (0.32g, 1.53mmol) and K3PO4 (0.43g, 2.04mmol) in dioxane (15mL) was exchanged with argon twice, then PdPPh3)4 (0.11g, 0.1mmol) were added to the above mixture. The reaction mixture was heated to 100C and stirred for 4h under argon atmosphere. The mixture was concentrated and the residue was purified by silica gel flash chromatography (eluting with ethyl acetate in 74 petroleum ether 5%) to give the product as a white solid (0.3g, yield=69%). 1H NMR (400MHz, CDCl3) delta 8.25 (s, 1H), 7.64 (m, 2H), 7.19 (s, 1H), 4.07 (d, J=7.0Hz, 2H), 3.99 (dd, J=11.3, 3.2Hz, 2H), 3.35 (td, J=11.8, 2.1Hz, 2H), 2.49 (s, 3H), 2.22-2.16 (m, 1H), 1.60 (s, 9H), 1.50-1.42 (m, 3H). LC/MS (ESI, m/z) 424.14 [M+H]+.

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, 867279-13-8, 4-Bromo-2-chloro-5-methylpyridine.

Reference:
Article; Wang, Beilei; Wu, Jiaxin; Wu, Yun; Chen, Cheng; Zou, Fengming; Wang, Aoli; Wu, Hong; Hu, Zhenquan; Jiang, Zongru; Liu, Qingwang; Wang, Wei; Zhang, Yicong; Liu, Feiyang; Zhao, Ming; Hu, Jie; Huang, Tao; Ge, Juan; Wang, Li; Ren, Tao; Wang, Yuxin; Liu, Jing; Liu, Qingsong; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 896 – 916;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 72583-83-6, 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.72583-83-6, name is 1-Methyl-1H-pyrazolo[3,4-b]pyridin-3-ylamine, molecular formula is C7H8N4, molecular weight is 148.17, as common compound, the synthetic route is as follows.

In a vial, to a mixture of intermediate 5 (0.02 g, 0.07 mmol), 7-methoxy-4,5- dihydronaphtho[l,2-d]thiazol-2-amine (0.02 g, 0.07 mmol) was added BOP (0.030 g, 0.069 mmol), DMF (0.3 mL), and DIEA (0.060 ml, 0.35 mmol). After 72 h, the reaction mixture was filtered and subjected to reverse phase HPLC purification to afford Example 1 (4.4 mg, 9.9 %). NMR (500MHz, OMSO-d6) delta 8.34 – 8.04 (m, 2H), 7.85 – 7.81 (m, 1H), 7.80 – 7.73 (m, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.42 – 7.29 (m, 2H), 7.27 – 7.12 (m, 2H), 6.91 – 6.79 (m, 2H), 3.83 (s, 2H), 3.33 (br s, 1H), 3.02 – 2.93 (m, 2H), 2.92 – 2.84 (m, 2H), 3.77 (s, 3H). LCMS m/z = 505.0 (M+H)+; HPLC purity > 96% with retention time 1.81 min. [method A]

The chemical industry reduces the impact on the environment during synthesis 72583-83-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J. P.; (183 pag.)WO2019/14300; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 112110-07-3, 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 1-(1-oxo-1,2-dihydroisoquinolin-5-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (345.9 mg, 0.888 mmol) and 5-(trifluoromethyl)pyridin-3-amine (120 mg, 0.74 mmol) in pyridine (3 mL) was added POCl3 (227 mg, 1.48 mmol) dropwise. The mixture was stirred at 25 C. for 4 h and at 40 C. for 3 h. Sat. NaHCO3 was added to adjust the pH to 7-8 and the mixture was extracted with ethyl acetate (30 mL*2). The combined organic layers were dried over MgSO4, filtered and the filtrates were concentrated under reduced pressure to afford crude product as a yellow oil. The crude product was then purified by preparative HPLC (37% to 57% (v/v) CH3CN and H2O with 0.05% HCl) to afford 1-(1-oxo-1,2-dihydroisoquinolin-5-yl)-5-(trifluoromethyl)-N-(5-(trifluoromethyl)pyridin-3-yl)-1H-pyrazole-4-carboxamide (130 mg, 37%). 1H NMR (400 MHz, DMSO-d6) delta ppm 5.67 (d, J=7.28 Hz, 1H), 7.26-7.31 (m, 1H), 7.68 (t, J=7.94 Hz, 1H), 7.94 (d, J=7.50 Hz, 1H), 8.44 (d, J=7.94 Hz, 1H), 8.53 (s, 1H), 8.60 (s, 1H), 8.75 (s, 1H), 9.12 (s, 1H), 11.18 (s, 1H), 11.64 (br d, J=4.63 Hz, 1H). LC-MS: (ES, m/z): [M+1]+ 467.9

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; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem