Pyridine-derivatives

Electric Literature of 6000-50-6 ,Some common heterocyclic compound, 6000-50-6, molecular formula is C7H10Cl2N2, 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.

2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride (CAS-No. 6000-50-6, 214 mg, 1.11 mmol) was added to a suspension of raw 4-nitrophenyl {4-[6-oxo-5-(quinolin-5-yl)-1,4,5,6- tetrahydropyridazin-3-yl]phenyl}carbamate (356 mg, 740 mumol) in dichloromethane (14 mL) and N,N-diisopropylethylamine (640 mul, 3.7 mmol). After stirring at r. t. for 2h the mixture was cooled to -20C and the precipitate was filtered off after standing for 12h and washed with cold dichloromethane. The precipitate was stirred in aqueous sodium hydroxide (20 mL, 1M), filtered, washed with water and dried under reduced pressure to give 175 mg (67% purity, 51% yield) of the title compound containing N-{4-[6-oxo-5-(quinolin-5-yl)-1,6- dihydropyridazin-3-yl] phenyl}-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide as minor impurity. (0693) LC-MS (Method 2): Rt = 0.78 min; MS (ESIpos): m/z = 463 [M+H]+ (0694) 1H-NMR (400MHz, DMSO-d6) delta [ppm]: 3.29 (dd, 1H), 3.42 (dd, 1H), 4.72 (dd, 1H), 4.81 (br d, 4H), 7.43 (d, 1H), 7.52 (d, 1H), 7.56 (dd, 1H), 7.60 – 7.65 (m, 2H), 7.68 – 7.76 (m, 3H), 7.97 (d, 1H), 8.50 (d, 1H), 8.58 – 8.64 (m, 3H), 8.92 (dd, 1H), 11.20 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6000-50-6, its application will become more common.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; BOeHNKE, Niels; BERGER, Markus; SOMMER, Anette; HAMMER, Stefanie; FERNANDEZ-MONTALVAN, Ernesto, Amaury; STELTEN-LUDWIG, Beatrix; GUeNTHER, Judith; MAHLERT, Christoph; GREVEN, Simone; SARKER, Abul, Basher; TAIT, Michael; (451 pag.)WO2019/149637; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 4930-98-7, 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 4930-98-7, name is 2-Hydrazinylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A. 5-Amino-1-(2-pyridinyl)-1H-pyrazole-4-carboxylic acid, ethyl ester A solution of 21.83 g of 2-hydrazinopyridine and 38.2 g of ethyl(ethoxymethylene)cyanoacetate dissolved in 150 ml of acetic acid and 50 ml of water was heated on a steam bath for approximately 16 hours. The reaction mixture was allowed to cool to room temperature and placed in a refrigerator whereupon crystals slowly formed. The precipitated solid was collected by filtration and washed with cold 50% aqueous ethanol to provide 23.62 g of 5-amino-1-(2-pyridinyl)-1H-pyrazole-4-carboxylic acid, ethyl ester. Yield 50.9%. MP=89-91 C.

According to the analysis of related databases, 4930-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; US4589905; (1986); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 62774-90-7 ,Some common heterocyclic compound, 62774-90-7, molecular formula is C7H5Cl2NO2, 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) Synthesis of 2,6-dichloro-N-(3-fluorobenzyl)-4-methyl-pyridine-3-carboxylic acid amideTo a solution of 17.4 g (84.4 mmol) of 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid in THF (340 ml) were added 10.6 ml (92.9 mmol) 3-fluorobenzylamine, 32.0 g (84.4 mmol) HATU and 35.0 ml (253.3 mmol) NEt3. The RM was then heated at 70 C for 16. After dilution with EtOAc (350 ml) the mixture was washed with a 4M aq. NH4CI sol., a 1M aq. NaHC03 sol. and brine. The organic layer was dried over MgS04 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 3:2) provided 19.5 g (62.3 mmol, 74%) 2,6-dichloro-N- (3-fluorobenzyl)-4-methyl-pyridine-3-carboxylic acid amide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62774-90-7, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; KUeHNERT, Sven; BAHRENBERG, Gregor; KLESS, Achim; SCHROeDER, Wolfgang; LUCAS, Simon; WO2012/52167; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 117519-09-2, 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, 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, HPLC of Formula: C6H4ClF3N2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H4ClF3N2

To a solution of 2-chloro-6-(trifluoromethyl)pyridin-3-amine (8) (5.0 g, 25 mmol) in acetonitrile (60 mL) was added NBS (5.0 g, 28 mmol). The mixture was stirred at reflux for 3 hours, concentrated and purified by silica gel chromatography and eluted with petroleum ether which gave 4-bromo-2-chloro-6-(trifluoromethyl)pyridin-3-amine (9) as a red semi-solid (6.0 g, 86% yield). 1H NMR (400 MHz, CDCl3) delta 7.68 (s, 1H), 4.93 (s, 2H). LCMS (ESI) m/z 275, 277 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117519-09-2, 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; PLANKEN, Simon; CHENG, Hengmiao; COLLINS, Michael Raymond; SPANGLER, Jillian Elyse; BROOUN, Alexei; MADERNA, Andreas; PALMER, Cynthia; LINTON, Maria Angelica; NAGATA, Asako; CHEN, Ping; US2019/233440; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13534-97-9, 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 13534-97-9 as follows.

Step 1: 5-Bromothiazolo[5,4-b]pyridin-2-amine To a suspension of 6-bromopyridin-3-amine (20.0 g, 115 mmol) and potassium thiocyanate (56.0 g, 576 mmol) in acetic acid (250 mL) was added dropwise a solution of bromine (23.88 g, 149 mmol) in acetic acid (100 mL) at room temperature. The reaction mixture was stirred at room temperature for 15 h. The solids were filtered out, and then the resulting solution was extracted with ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate, filtered and the filtrate was evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (solvent gradient: 0-10% methanol in DCM) to yield 18 g (68%) of the title compound. LCMS (ESI): [M+H]+=230/232.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13534-97-9, its application will become more common.

Reference:
Patent; Genentech, Inc.; Braun, Marie-Gabrielle; Garland, Keira; Hanan, Emily; Purkey, Hans; Staben, Steven T.; Heald, Robert Andrew; Knight, Jamie; Macleod, Calum; Lu, Aijun; Wu, Guosheng; Yeap, Siew Kuen; (183 pag.)US2018/65983; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 133362-99-9, 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. 133362-99-9, name is 2-Pyridin-4-ylbenzoic acid, molecular formula is C12H9NO2, 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 115 2-(4-Pyridinyl)-N-(4-{[2-(2-pyridinyl)ethyl]amino}phenyl)-benzamide The title compound was obtained from tert-butyl 4-aminophenyl[2-(2-pyridinyl)ethyl]carbamate and 2-(4pyridinyl)benzoic acid in the same manner as in Example 101. 1H-NMR (DMSO-d6): delta2.96 (2H, t, J=7.3 Hz), 3.28-3.44 (2H, m), 5.55 (1H, t, J=5.7 Hz), 6.52 (2H, d, J=8.8 Hz), 7.18-7.38 (4H, m), 7.46 (2H, dd, J=1.4 Hz, 10.2 Hz), 7.49-7.68 (4H, m), 7.70 (1H, dt, J=1.8 Hz, 7.6 Hz), 8.51 (1H, d, J=4.1), 8.57 (2H, d, J=6.0 Hz), 9.94 (1H, s) (+)APCI-MS (m/z): 395 (M+H)+

According to the analysis of related databases, 133362-99-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takasugi, Hisashi; Terasawa, Takeshi; Inoue, Yoshikazu; Nakamura, Hideko; Nagayoshi, Akira; Ohtake, Hiroaki; Furukawa, Yoshiro; Mikami, Masafumi; Hinoue, Kazumasa; Ohtsubo, Makoto; US2004/58903; (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. 74115-13-2, name is 5-Bromo-3-pyridinol, molecular formula is C5H4BrNO, 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. HPLC of Formula: C5H4BrNO

12a. 5-((2S)-Azetidinylmethyloxy)-3-bromopyridine dibenzoate Triphenylphosphine (4.01 g, 15.3 mmol) and DEAD (2.43 mL, 15.3 mnol) were dissolved in 30 mL of THF at 0 C., and the mixture was stirred for 10 minutes. Samples of 1-t-butyloxycarbonyl-2-(S)-azetidinemethanol (2.86 g, 15.3 mmol, Step 7c above) and 3-bromo-5-hydroxypyridine.(1.51 g, 10.2 mmol, Step 10c above) were added, and the mixture was stirred for 40 hours at room temperature. The volatile components were removed under vacuum, and the residue was triturated with hexane. The separated hexane fraction was concentrated, and the residue was chromatographed (silica gel; hexane/ether, 10:1 to 10:2) to afford 5-bromo-3-((1-t-butyloxycarbonyl-(2S)-azetidinyl)methoxy)pyridine as a colorless oil (1.669 g): 1 H NMR (CDCl3, 300 MHz) delta 1.42 (s, 9H), 2.31 (m, 2H), 3.89 (m, 2H), 4.12 (m, 1 H), 4.322 (m, 1 H), 4.52 (m, 1 H), 7.43 (m, 1 H), 8.29 (m, 2H); MS (CI/NH3) m/z 344 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 74115-13-2.

Reference:
Patent; Abbott Laboratories; US6133253; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 866546-07-8, 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 866546-07-8 as follows.

[94] Step 5. N-(3 -((5-Chloro- 1 Eta-rhonuetachi)1omicronGamma2.3 -blpyridin-3 -yl)(hvdroxy)-methyl)-2.4- difluorophenyl)- 1.1.2.2.3.3.3 -d7-propane- 1 -sulfonamide (24):; To a solution offormylsulfonamide 23 (50.0 mg, 0.185 mmol) in MeOH/Water 1 : 1 (1 mL) was added 5- chloroazaindole 6a(i) (30.0 mg, 0.196 mmol, Adesis, Inc.) followed by K2CO3 (171 mg, 1.24 mmol). The resulting solution stirred at room temperature for 3 days then was neutralized to pH 7 with 4N HC1 and extracted with EtO Ac (3 x 50 mL). The organic layers were combined, washed with water, dried (Na2S04), filtered and concentrated under reduced pressure to afford azaindole 24 (60 mg, 77%) as a tan solid which was used without further purification. MS (ESI) 421.0 [(M – H) “].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,866546-07-8, its application will become more common.

Reference:
Patent; CONCERT PHARMACEUTICALS INC.; TUNG, Roger; MASSE, Craig E.; SILVERMAN, I. Robert; WO2011/60216; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2002-04-2, 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.2002-04-2, name is 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-amine, molecular formula is C7H6N4S, molecular weight is 178.21, as common compound, the synthetic route is as follows.

General procedure: An equimolar amount of 5-(pyridin-4-yl)-1,3,4-thiadiazol-2-amine (3c) dissolve in 10-15mL of tetrahydrofuran (THF), add 2-3 drops of triethylamine, to this solution add 1.5mol different aryl chlorides gradually, continuous stirring for 3h on ice bath(0C). After completion of reaction solid will precipitate out, washed with sodium bicarbonate solution to remove excess of chloride and recrystallized from ethanol to get pure compound.

The chemical industry reduces the impact on the environment during synthesis 2002-04-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Patel, Harun; Jadhav, Harsha; Ansari, Iqrar; Pawara, Rahul; Surana, Sanjay; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 1 – 9;,
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. 16867-03-1, name is 2-Amino-3-hydroxypyridine. A new synthetic method of this compound is introduced below., name: 2-Amino-3-hydroxypyridine

15.6 g (141.6 mmol) of 2-amino-3-hydroxypyridine are initially charged in 300 ml of glacial acetic acid, 15.6 g (141.6 mmol) of 2-amino-3-hydroxypyridine are initially charged in 300 ml of glacial acetic acid, [0294] 5.1 g of 5% rhodium/ carbon catalyst are added and the mixture is hydrogenated in a 600 ml vessel (material: Hastelloy) at room temperature (20 C.) at 4.5 bar for about 16 hours. The entire reaction mixture is then filtered (removal of the catalyst) and concentrated under reduced pressure, and the residue that remains is recrystallized from an ethanol/ether mixture. This gives 5.9 g (23.9% of theory) of a (2:1) mixture of 2-amino-3-hydroxypyridine and 2-amino-3,4,5,6-tetrahydropyridin-2-ol acetate CH NMR spectrum: some Py-H) which can be used for the next reaction. [0295] 1H NMR (600 MHz, D2O) delta 1.79 (br., m, 1H), 1.90-1.92 (m, 1H), 1.99-2.00 (br., m, 1H), 2.22 (br., m, 1H), 3.37 (m, 2H), 4.52 (m, 1H), 6.77-6.78 (m, 1H), 7.18-7.19 (m, 1H), 7.28-7.29 (m, 1H) ppm; At room temperature, 1.0 g (5.74 mmol) of the (2:1) mixture of 2-amino-3-hydroxypyridine and 2-amino-3,4,5,6-tetrahydropyridin-2-ol acetate (cf. step 1) are stirred with 1.26 g (7.79 mmol) of 1,1?-carbonyldiimidazole (CDI), 39.9 mg of 4-dimethylaminipyridine (DMAP) in 6 ml of dichloromethane, and 1.2 ml of triethylamine are added. The entire reaction mixture is then stirred at room temperature for another about 24 hours. The reaction mixture is then concentrated under reduced pressure, the residue that remains is taken up in ethyl acetate and the organic phase is washed with water. The organic phase is separated off and then dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue that remains is purified chromatographically by medium-pressure chromatography (cyclohexane/acetone gradient). This gives 753.0 mg (93.2% of theory) of a mixture of oxazolo[4,5-b]-5,6,7,7a-tetrahydropyridin-2(4H)-one [0301] and oxazolo[4,5-b]pyridin-2(3H)-one (cf. WO 2010/135014 A1) (1H NMR spectrum: some Py-H and LC-MS m/z: 137.0) which can be used for the next reaction. [0302] LC-MS (ESI positive): m/z found: 141.0 [M++H]. [0303] C6H8N2O2 calculated: 140.0.

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, 16867-03-1, 2-Amino-3-hydroxypyridine.

Reference:
Patent; Jeschke, Peter; Schindler, Michael; Woelfel, Katharina; Ebbinghaus-Kintscher, Ulrich; Voerste, Arnd; Malsam, Olga; Losel, Peter; Goergens, Ulrich; US2014/113824; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem