Category: pyridine-derivatives

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

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

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

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

Related Products of 5654-97-7, 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. 5654-97-7, name is 1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one, 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.

Monomer 9: 3-Dimethylaminomethylene-7-azaoxindole This monomer was generated in situ (during library synthesis) from 7-azaoxindole and dimethylformamide di-t-butylacetal in DMF.

According to the analysis of related databases, 5654-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SmithKline Beecham Corporation; US6369086; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 178876-86-3, 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 178876-86-3, name is Methyl 5-bromo-6-oxo-1,6-dihydropyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Pd(PPh3)2C12 (30 mg, 0.0424 mmol) was added to a nitrogen flushed mixture of methyl 5- bromo-6-oxo- 1 ,6-dihydropyridine-2-carboxylate (98.4 mg, 0.424 mmo 1), 4- isopropylphenylacetylene (92 mg, 0.636 mmol), Cul (16.1 mg, 0.0848 mmol) and Et3N (600 jil) in THF (1.5 ml) and the mixture was heated at 100 C in microwave reactor for 15 mm. Solvent evaporated and residue purified by flash chromatography using 20-33% EtOAc aseluent. Yield: 55.5 mg (44%); beige solid.

According to the analysis of related databases, 178876-86-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KANCERA AB; HAMMER, Kristin; JOeNSSON, Mattias; KRUeGER, Lars; (230 pag.)WO2017/108282; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 10201-73-7 ,Some common heterocyclic compound, 10201-73-7, molecular formula is C6H8N2O, 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.

General procedure: To a mixture of 2-aminopyridine (0.5 mmol, 1 equiv), p-TSA (0.4 mmol,0.8 equiv), 1-butylpyridinium bromide (1.5 mmol, 3 equiv) in a 50 mL Schlenk tube were added 1,2-dimethoxyethane (2 mL) under air. Then H2O2 (1.2 mmol, 2.4 equiv) was added. The mixture was stirred at 80C for 24 h. And then the mixture was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the products.

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. 10201-73-7, 2-Amino-4-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Tong; Zhou, Wen; Wang, Jing; Li, Xue; Guo, Jun-Wen; Wang, Bin; Tetrahedron Letters; vol. 55; 36; (2014); p. 5058 – 5061;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 55589-47-4, 3-Methylpicolinaldehyde, 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, 55589-47-4, blongs to pyridine-derivatives compound. HPLC of Formula: C7H7NO

To a solution of X4-172-4 (1.0 g, 7.34 mmol), L-proline (338 mg, 2.94 mmol) and 3-methylpicolinaldehyde (1.07 g, 8.81 mmol) in MeOH (200.0 mL) was added methanamine aq. (8 mL, 40percent). The solution was stirred at room temperature overnight. The solvent was removed under reduce pressure and purified by column chromatography to give X4- 172-1 (1.4 g, 70.5 percent yield) as yellow solid. LCMS (Agilent LCMS 1200-6120, Column: Waters X-Bridge C18 (50 mm*4.6 mm*3.5 jim); Column Temperature: 40 °C; Flow Rate: 2.0 mL/min; Mobile Phase: from 90percent [(total 10mM AcONH4) water/CH3CN = 9/1 (v/v)] and 10percent [(total 10mM AcONH4) water/CH3CN = 1/9 (v/v)] to 10percent [(total 10mM AcONH4) water /CH3CN =9/1 (v/v)] and 90percent [(total 10mM AcONH4) water/CH3CN = 1/9 (v/v)] in 1.6 mm, then under this condition for 2.4 mm, finally changed to 90percent [(total 10mM AcONH4) water/CH3CN = 9/1 (v/v)] and 10percent [(total 10mM AcONH4) water/CH3CN = 1/9 (v/v)] in 0.1 mm and under this condition for 0.7 mm). Purity: 61.0 percent. Rt = 1.09 mm; MS Calcd.: 270.1; MS Found: 271.1 [M + H]t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55589-47-4, its application will become more common.

Reference:
Patent; X4 PHARMACEUTICALS, INC.; BOURQUE, Elyse Marie Josee; SKERLJ, Renato; (279 pag.)WO2017/223229; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 39977-44-1, Methyl 6-(hydroxymethyl)picolinate, 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, Application In Synthesis of Methyl 6-(hydroxymethyl)picolinate, blongs to pyridine-derivatives compound. Application In Synthesis of Methyl 6-(hydroxymethyl)picolinate

EXAMPLE 18 Preparation of 6-formylpyridine-2-carboxylic Acid Methyl Ester (IVo) A solution of 3 g of 6-hydroxymethylpyridine-2-carboxylic acid methyl ester (16.5 mmol) in 70 ml of 1,2-dichloroethane containing 15 g of manganese dioxide (165 mmol) is heated under reflux for 4 hours with removal of the water formed continuously. The solid is removed by filtration on celite and then the dichloromethane is evaporated off. The title product is isolated by chromatography on a silica column (eluent: dichloromethane/ethyl acetate; 70:30). 2.33 g of a yellow oil are recovered. Yield: 79% 1 H NMR (CDCl3) delta: 1.36 (t, 3H); 4.41 (m, 2H); 8.13 (dd, 1H); 8.24 (t, 1H); 8.32 (dd, 1H); 10.02 (s, 1H). IR (film) ?: 1700 cm-1 (C=O).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39977-44-1, Methyl 6-(hydroxymethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; Pierre Fabre Medicament; US6020345; (2000); A;,
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.136888-26-1, name is 5,6-Dichloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one, molecular formula is C7H4Cl2N2O, molecular weight is 203.0255, as common compound, the synthetic route is as follows.Recommanded Product: 5,6-Dichloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

Example 51 5,6-Dichloro-3-(2-furoyl)-4-azaoxindole-1-N-t-butyl carboxamide 5,6-Dichloro-3-(2-furoyl)-4-azaoxindole was first prepared according to the procedure of Example 1B, using 5,6-dichloro-4-azaoxindole (763 mg, 3.76 mmol), sodium (0.43 g, 18.8 mmol), ethyl-2-furoate (1.05 g, 7.5 mmol) and ethanol (25 mL). Yield: 0.98 g (88%). The title compound was prepared from 5,6-dichloro-3-(2-furoyl)-4-azaoxindole according to the procedure of Example 1C, using 5,6-dichloro-3-(2-furoyl)-4-azaoxindole (721 mg, 2.41 mmol), triethylamine (1.8 mL, 15.4 mmol), t-butyl isocyanate (1.4 mL, 12.3 mmol) and DMSO (20 mL). The reaction time was 22 hours. The crude product was triturated with methanol and recrystallized from hexane. Yield: 218 mg (23%). Analysis calc’d for C17H15Cl2N3O4: C 51.53, H 3.82, N 10.60. Found: C 51.70, H 3.81, N 10.57. M.p. 205 – 206C. 1H NMR (DMSO-d6) delta 9.37 (br s, 1H), 8.32 (s, 1H), 7.91 (s, 1H), 7.85 (d, J = 3.7 Hz, 1H), 6.69 (d, J = 3.7 Hz, 1H), 1.38 (s, 9H). IR (KBr disc) 1730, 1620, 1605, 1590, 1555, 1535 cmmin1. MS m/e (relative percent) 397(0.5), 395(2), 298(21), 296(33), 230(62), 228(100), 95(40).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,136888-26-1, 5,6-Dichloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; EP436333; (1991); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem