Day: June 9, 2021

Electric Literature of 67515-76-8, 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 67515-76-8, name is Methyl 5-aminopicolinate. This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of methyl 5-aminopicolinate (70mg, 0.460 mmol) in THF (3 mL) was added a solution of LAH (1 M in THF) (0.920 mL, 0.920 mmol) at 0 C. The mixture was allowed to warm to room temperature and stirred overnight. After 16 h, thereaction was quenched with water (0.1 mL) at 0 C. A solution of sodium hydroxide (2N, 0.1 mL) was subsequently added followed by an additional quantity of water (0.3 mL). Magnesium sulfate was added and the mixture was stirred for 1 hour before being filtered over a pad of celite and washed with THF. The filtrate was concentrated in vacuo to afford Intermediate 385A (35 mg, 0.282 mmol, 61.3 % yield) as a yellow solid. Thismaterial was taken on without further purification. LC-MS. Method H, RT = 0.44 mm, MS (ESI)m/z: 125.1 (M+H). ?HNMR(400 MHz, DMSO-d6) 7.80-7.88 (m, 1H), 7.05-7.16 (m, 1H), 6.83-6.96 (m, 1H), 4.88-5.04 (m, 1H), 4.27-4.41 (m, 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 67515-76-8, Methyl 5-aminopicolinate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 66572-56-3 ,Some common heterocyclic compound, 66572-56-3, molecular formula is C6H4BrNO2, 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.

Preparation of Example 4 (S)-N-((S)-Cyclohexyl-2-{(S)-2-{2-[2,3-dihydro-indol-1-yl)-pyridin-4-yl]-pyrrolidin-1-yl}-pyrrolidin-1-yl)-2-oxo-ethyl)-2-methylamino-propionamide 2-Bromo-N-methoxy-N-methyl-isonicotinamide (1)To a solution of 2-bromo-pyridine-4-carboxylic acid (11.83 g, 58.56 mmol) in DMSO (100 mL) are added HOBt (9.49 g, 70.30 mmol) and HBTU (26.70 g, 70.30 mmol). The mixture is stirred at room temperature for 20 min, then N,O-dimethylhydroxylamine HCl (6.28 g, 64.41 mmol) and diisopropylethylamine (22.72 g, 175.68 mmol) are added to the mixture. After stirring at room temperature for 3 h, the reaction mixture is diluted with water and extracted with EtOAc. The combined organic layers are washed with water, sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated down. The crude product is purified by flash chromatography on silica gel (EtOAc/Hexane: 10%40%) to give 2-Bromo-N-methoxy-N-methyl-isonicotinamide (12.4 g, 86%) as a white solid. M/Z=245.0

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,66572-56-3, its application will become more common.

Reference:
Patent; Novartis AG; US2011/15232; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 19828-20-7 , The common heterocyclic compound, 19828-20-7, name is 2-Amino-5-acetylpyridine, molecular formula is C7H8N2O, 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 3: N-(5-Acetyl-pyridin-2-yl)-4-(3-dimethylamino-propoxy)-benzenesulfonamide The flask was charged with 1-(6-amino-pyridin-3-yl)-ethanone (100 g, 0.74 mol. Ref: J. Med. Chem. 1973, 16 (8), 959-961) and was purged with nitrogen. To this was added 500 mL pyridine, and the mixture was heated to 60 C.; a pale amber solution was obtained. To it was added 230 g 4-[3-(dimethylamino)propoxy]benzenesulfonyl chloride (230 g, 0.74 mol) in portions over the course of one hour. After the addition was complete the mixture was heated to 60 C. for 90 minutes. It was allowed to cool to 35 C., and was then poured into a vigorously stirred mixture of 2L ethyl acetate and 1170 g dibasic potassium phosphate dissolved in 2 L water. The mixture was stirred for 15 minutes. The resulting precipitate was collected by filtration. It was washed with 2*1 L ethyl acetate and air dried to give 330 g of crude tan solid. 1H-NMR (400 MHz, DMSO) delta 8.60 (s, 1H), 7.96 (d, 1H), 7.77 (d, 2H), 6.95-7.00 (m, 3H), 4.02 (t, 2H), 2.60 (t, 2H), 2.42 (s, 3H), 2.33 (s, 6H), 1.84-1.96 (m, 2H); [M+H]+378.

The synthetic route of 19828-20-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; US2007/135438; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 790696-96-7, 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. 790696-96-7, name is 2-chloro-3-methylisonicotinaldehyde, molecular formula is C7H6ClNO, 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.

(2-Chloro-3-methylpyridin-4-ylmethyl)-cyclopropylamine (Q) A sol. of aldehyde P (4.70 g, 30.2 mmol) and cyclopropylamine (4.20 ml, 60.4 mmol) in MeOH (65 mL) was stirred at rt for 4 h. NaBH4 (1.55 g, 39.2 mmol) was added and the mixture was stirred at rt for 12 h. Water and subsequently aq. 1M NaOH were added, and the solvents were partially removed under reduced pressure. The water phase was extracted with CHUCK (2x). The combined org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC yielded the title compound (4.66 g, 79%). LC-MS: RT = 0.43 min; ES+ =197. 1.

According to the analysis of related databases, 790696-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2005/54243; (2005); 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.53636-56-9, name is Methyl 3-bromo-2-pyridinecarboxylate, molecular formula is C7H6BrNO2, molecular weight is 216.03, as common compound, the synthetic route is as follows.COA of Formula: C7H6BrNO2

N-((4-chloro-2-methylphenyl)(phenyl)methyl)-2-(2-(2-(hydroxymethyl)pyridin-3-yl)benzofuran-5- yl)acetamidea) (3-bromopyridin-2-yl)methanolTo a solution of methyl 3-bromopicolinate (1 g, 4.6 mmol) in MeOH (50 mL) at 0 C was added NaBH4 (883 mg, 23.2 mmol). The reaction mixture was stirred at rt overnight, followed by concentration under reduced pressure. The resultant residue was dissolved in EtOAc (50 mL), washed with aq. NH4C1 (3 x 20 mL), dried over Na2S04, filtered, and concentrated to afford the title compound (101 g, 92%) as a white solid. LCMS-P 1 : 190/192 [M+H]+; Rt: 1.070 min

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53636-56-9, Methyl 3-bromo-2-pyridinecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; BOHNERT, Gary, J.; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; SUNG, Leonard; WO2013/19682; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 63071-10-3, (4-Chloropyridin-2-yl)methanol, 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: C6H6ClNO, blongs to pyridine-derivatives compound. HPLC of Formula: C6H6ClNO

Example 307 Synthesis of (4-chloropyridin-2-yl)methyl 4-methylbenzenesulfonate. Sodium hydride (44 g, 60%, 1.096 mol) was added to a cooled (0 C.) solution of (4-chloropyridin-2-yl)methanol (80 g, 548 mmol) in THF (1500 mL) at 0 C. The mixture was stirred at 0 C. for 1 h, and tosyl chloride (104 g, 548 mmol) was added. After stirring at 0 C. for another 3 h, the mixture was quenched with H2O (50 mL), and extracted with ethyl acetate (120 mL*3), the combined organic layers were washed with brine, dried over with anhydrous magnesium sulphate, filtered, and concentrated to afford (4-chloropyridin-2-yl)methyl 4-methylbenzenesulfonate (162 g, crude) as a brown oil which was used in the next step without purification. ESI-MS [M+H]+: 296.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63071-10-3, (4-Chloropyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16133-25-8, Pyridine-3-sulfonyl chloride, 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, COA of Formula: C5H4ClNO2S, blongs to pyridine-derivatives compound. COA of Formula: C5H4ClNO2S

4-(a) tert-Butyl (tert-butoxycarbonyl{6-[(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)acetate To 14 ml of a methylene chloride solution containing 640 mg (3.60 mmol) of 3-pyridylsulfonyl chloride were added 1.20 g (3.56 mmol) oftert-butyl [(6-aminomethylpyridin-2-yl)tert-butoxycarbonylamino]acetate obtained by the same manner as in Reference example 1-(e) and 2.24 ml (16.2 mmol) of triethylamine, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, to the reaction mixture was added a 5percent aqueous potassium hydrogen sulfate solution, and the mixture was extracted with chloroform. The organic layer was successively washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (eluent; n-hexane:ethyl acetate=1:1–>1:2 (V/V)), and the fractions containing the objective material were concentrated under reduced pressure to obtain 1.45 g of the title compound as colorless oil. (Yield: 85percent) Mass spectrum (CI, m/z): 479 (M++1). 1H-NMR spectrum (CDCl3, delta ppm): 9.06 (d, J=2.2 Hz, 1H), 8.71 (dd, J=4.6, 1.5 Hz, 1H), 8.13-8.08 (m, 1H), 7.68 (d, J=8.2 Hz, 1H), 7.52 (dd, J=8.2, 7.4 Hz, 1H), 7.38-7.32 (m, 1H), 6.77 (d, J=7.4 Hz, 1H), 5.80 (t, J=5.1 Hz, 1H), 4.40 (s, 2H), 4.24 (d, J=5.1 Hz, 2H), 1.53 (s, 9H), 1.46 (s, 9H).

The synthetic route of 16133-25-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ube Industries, Ltd.; EP2476678; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 4548-45-2, 2-Chloro-5-nitropyridine, 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, 4548-45-2, blongs to pyridine-derivatives compound. Recommanded Product: 2-Chloro-5-nitropyridine

To a stirring solution of compound 20 (5.0 g, 31.5 mmol) in acetic acid (50 ml) was added iron powder (8.8 g, 157.6 mmol) in small portion at room temperature, the reaction was exothermic and the temperature rise to 80C, end of added and kept the temperature at 40-50C and stirred for 2h. The reaction was filtered through celite and washed with little acetic acid, the filtrate was evaporated to dryness, adjusted pH=8 with saturated solution of sodium bicarbonate, extracted with dichloromethane (100 ml x 5). The combined organic phase was washed with brine, dried over Na2S04, filtered and concentrated to afford crude compound 84 (3.9 g, yield 96%) as a brown solid, used directly in next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4548-45-2, its application will become more common.

Reference:
Patent; SHANGHAI DE NOVO PHARMATECH CO LTD.; GAO, Daxin; YANG, Heping; YU, Yajun; WO2013/91502; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5470-70-2, 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. 5470-70-2, name is Methyl 6-methylnicotinate. A new synthetic method of this compound is introduced below.

0.471 g (1.0 equivalent) of N-bromosuccinimide and 64 mg (0.1 equivalent) of benzoyl peroxide are added to a solution of 0.4 g of the product obtained in the preceding Stage 1 in 15 ml of carbon tetrachloride. The solution is brought to reflux for 6 hours, then filtered and evaporated under reduced pressure. The residue is purified by chromatography on silica gel (dichloromethane/ethyl acetate: 95/5) to produce 0.262 g of the expected product. [ Yield: 43% MS: MH+ 231

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5470-70-2, Methyl 6-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Dublanchet, Anne-Claude; Compere, Delphine; Cluzeau, Philippe; Blais, Stephane; Denis, Alexis; Ducrot, Pierre; Courte, Karine; Descamps, Sophie; US2004/72871; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 10592-27-5 ,Some common heterocyclic compound, 10592-27-5, molecular formula is C7H8N2, 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 2; A solution of Br2 (2.78 ml, 8.64 g, 54 mmole) in dry dichloromethane (40 ml) was added dropwise over a period of 1 h 45 min to a stirred and cooled (-10C) solution of 2.3-dihydro-1H-pyrrolo[2,3-b]pyridine (6.5 g,54 mmole) in a mixture of dry dichloromethane (60 ml) and pyridine (6 ml). The suspension was stirred at 0C for 2 hrs, poured into a mixture of NaHCO3 (120 ml) and saturated aqueous Na2S2O3 (15 ml) and extracted with a solution of ethyl acetate/methanol (3X200 ml). The organic layers were concentrated to afford 3.7 g of 5-bromo- 2,3-dihydro- 1H-pyrrolo[2,3-b]pyridine (2) after purification by flash chromatography using dichloromethane as eluent (35% yield). 1H NMR (400 MHz, DMSO-D6) delta ppm 2.98 ( t, J = 8.54 Hz, 2H ) 3.48 (t, J=8.55 Hz, 2H) 6.58 (bs, 1 H) 7.37(s,1 H) 7.71 (s,1 H)

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. 10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; EP2070928; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem