Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 1160791-13-8, 2-Amino-6-bromothiazolo[5,4-b]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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

General procedure: The mixture of 6-bromobenzo[d]thiazol-2-amine (2.0 g, 8.73 mmol), carbonyldimidazole (4.24 g, 26.2 mmol) and dried DMF (20 ml) was stirred at room temperature for 8 h, added cyclopropanamine (0.76 g, 13.2 mmol), then stirred at room temperature for another 8 h. The volatile was removed under reduced pressure. Water (30 ml) was added to the residue. The resulting suspension was stirred. After standing, the solid was collected by filtration, dried to produce 8a (1.77 g, 65%) as white solid. 4.1.1.9 1-(6-Bromothiazolo[5,4-b]pyridin-2-yl)-3-(2-(morpholinoethyl)urea (8i) White solid; Yield 86%; mp: 152-154 C; 1H NMR (DMSO-d6) delta 11.13 (s, 1H, NH), 8.01 (d, J = 8.3 Hz, 1H, Ar-H), 7.48 (d, J = 8.4 Hz, 1H, Ar-H), 6.81 (s, 1H, NH), 3.60 (s, 4H, OCH2*2), 3.29 (d, J = 5.2 Hz, 2H, CH2), 2.41 (s, 6H, NCH2*3). MS (ESI, m/z): Calcd for [M+H]+ C13H17BrN5O2S: 386, 388, found 386, 388.

The synthetic route of 1160791-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xie, Xiao-Xiao; Li, Huan; Wang, Juan; Mao, Shuai; Xin, Min-Hang; Lu, She-Min; Mei, Qi-Bing; Zhang, San-Qi; Bioorganic and Medicinal Chemistry; vol. 23; 19; (2015); p. 6477 – 6485;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 113118-82-4, 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. 113118-82-4, name is 5-Chloronicotinaldehyde, molecular formula is C6H4ClNO, 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.

5.1.96 EXAMPLE 96: SYNTHESIS OF 2-(5-CHLOROPYRIDIN- 3-YL)-8-OXO-9-(2-(TRIFLUOROMETHYL)PHENYL)-8,9-DIHYDRO-7H-PURINE-6-CARBOXAMIDE; EPO [00432] A. Z-CS-Chloropyridin-S-yO-S-oxo^-CZ^trifluoromethyOphenyO-S^- dihydro-7H-purine-6-carboxamide. (Z)-l-(2-Amino-l ,2-dicyanovinyl)-3-(2- (trifluoromethyl)phenyl)urea {See Example 50.A) (0.15 g, 0.51 mmol), 5- chloronicotinaldehyde (0.14 g, 0.99 mmol), and triethylamine (0.10 ml, 0.72 mmol) were combined in methanol (7.0 mL) and stirred at room temperature overnight. Excess solvent was removed under reduced pressure and the resulting residue was purified by reverse-phase preparatory HPLC (30-80% acetonitrile + 0.1% TFA in H2O + 0.1% TFA, over 30 min). Clean fractions were neutralized with ammonium hydroxide and solvent removed under reduced pressure. The resulting material was taken up in ethyl acetate, washed successively with potassium carbonate, water, and brine. The solution was dried over sodium sulfate, filtered and solvent removed under reduced pressure to provide the product as an off white solid (0.035 g, 0.08 mmol, 16% yield). 1H NMR (400 MHz, DMSO-^5) delta 12.07 (bs, IH), 9.23 (s, IH), 8.95 (s, IH), 8.59 (m, 2H), 7.93 (m, 2H), 7.78 (m, 2H), 7.63 (bs, IH); MS (ESI) m/z 435.0 [M+l]+; mp 230-2320C.

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 113118-82-4, 5-Chloronicotinaldehyde.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51494; (2008); 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. 1256805-54-5, name is 6-Chloro-4-methoxypyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H7ClN2O

To a solution of XII-1 (0.50 g, 1 .97 mmol) in pyridine (10 mL) was added X-1 (0.18 g, 1 .25 mmol) and DMAP (0.012 g, 0.09 mmol). The reaction mixture was heated at 80 C for 16h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was concentrated under vacuum. The residue was diluted with H20 (100 mL), 1 N HCI (50 mL) and extracted with EtOAc (100 mL). The organic layer was separated, dried over anhydrous Na2S04 and concentrated under vacuum. The crude obtained was purified by column chromatography (silica, 100-200 mesh, 40% EtOAc in hexane) to afford 6-chloro-N-(2,5-difluoropyridin-3-yl)-1H-indole-3-sulfonamide 1-1 (0.05 g) as an off-white solid. (1207) Yield: 7%. (1208) Basic LCMS Method 1 (ES ): 342 (M-H)-, 97% purity. (1209) 1H NMR (400 MHz, DMSO-cfe) d 7.25 (dd, J=8.31 , 1.47 Hz, 1 H), 7.54 (s, 1 H), 7.71-7.81 (m, 2H), 7.89 (s, 1 H), 8.16 (d, J=2.93 Hz, 1 H), 10.73 (brs, 1 H), 12.22 (brs, 1 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, 1256805-54-5, 6-Chloro-4-methoxypyridin-3-amine.

Reference:
Patent; UCB PHARMA GMBH; PEGURIER, Cecile; PROVINS, Laurent; CARDENAS, Alvaro; LEDECQ, Marie; MUELLER, Christa E.; HOCKEMEYER, Joerg; EL-TAYEB, Ali; BOSHTA, Nader; RASHED, Mahmoud; (165 pag.)WO2019/243303; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55052-27-2 ,Some common heterocyclic compound, 55052-27-2, molecular formula is C7H5ClN2, 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.

At room temperature, concentrated aqueous ammonia (40 mL) was added drop-wise to 6-chloro-7-azaindole (3.20 g, 0.024mol), after the tube is heated, the reaction is heated at 120 C for 5h. The reaction is complete, cooling, filter and then obtained a brown solid product (2.00 g, 72%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55052-27-2, its application will become more common.

Reference:
Patent; Ding Min; (8 pag.)CN108997343; (2018); A;,
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. 832715-99-8, name is 6-(tert-Butyl)nicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-(tert-Butyl)nicotinic acid

To a solution of Intermediate 3 (250 mg, 0.83 mmol), tert-butylcarboxylic acid(89 mg, 0.88 mmol), 6-(tert-butyl)pyridine-3-carboxylic acid (158 mg, 0.88 mmol), EDC (270 mg, 1.25 mmol) and HOBT (150 mg, 0.83 mmol) in DCM (5 mL) was added DIPEA (250 muL, 1.66 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction was quenched with water (10 mL). The organic layer was separated, dried (MgSO4), concentrated in vacuo and chromatographed (SiO2, 20: 1 EtOAc/MeOH), yielding the title compound (140 mg, 34%) as a white solid after freeze-drying with 1 : 1 MeCN-water. deltaH (d6-DMSO) 8.30 (s, IH), 7.61 (s, IH), 7.41-7.37 (m, 2H), 7.32 (d, J 8.1 Hz, IH), 7.21 (dd, J8.4, 1.4 Hz, IH), 7.07 (s, IH), 4.30-4.18 (m, IH), 3.93-3.90 (m, IH), 3.82 (d, J 11.6 Hz, IH), 3.78-3.75 (m, 4H), 3.59 (dd, J 11.7, 3.2 Hz, IH), 3.57-3.50 (m, 2H), 3.22-3.14 (m, 2H), 2.99 (s, 6H), 1.33 (s, 9H). LCMS (ES+) 463 (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, 832715-99-8, 6-(tert-Butyl)nicotinic acid.

Reference:
Patent; UCB PHARMA S.A.; ALI, Mezher, Hussein; BROWN, Julien, Alistair; DE CANDOLE, Benjamin, Charles; HUTCHINSON, Brian, Woodside; LANGHAM, Barry, John; NEUSS, Judi, Charlotte; QUINCEY, Joanna, Rachel; TREVITT, Graham, Peter; WO2010/146351; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 193274-02-1 , The common heterocyclic compound, 193274-02-1, name is tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate, molecular formula is C19H25N3O3, 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 D. 3a(R)-Benzyl-2-methyl-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-3-one (L)-tartrate To a 2 liter, round bottom flask, equipped with a mechanical stirrer, addition funnel, and a thermocouple was added, sequentially, 3a-(R,S)-benzyl-2-methyl-3-oxo-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]-pyridine-5-carboxylic acid tert-butyl ester (prepared according to Step C, 51.5 g, 0.15 moles, 1.0 equivalents) and methylene chloride (515 ml, 10 volumes). The mixture was agitated to form a solution which was then cooled to an internal temperature of 0 C.-5 C. To the cooled mixture was added trifluoroacetic acid (TFA, 130 ml, 192 g, 1.68 moles, 11.2 eq., 2.5 volumes). The TFA was added via the addition funnel over 15 minutes while maintaining an internal temperature of 0 C.-5 C. The reaction mixture was warmed to about 20 C. over 3 hours and then the reaction mixture was cooled to 10 C.-15 C. To the cooled reaction mixture was added sodium carbonate (92 g, 0.868 moles) in water (920 mL) over 20 minutes. The pH was 7.5. The reaction mixture was transferred to a 2 liter separatory funnel and allowed to settle. The organic portion was decanted and the aqueous portion was extracted with methylene chloride (130 ml, 2.5 volumes). The combined organic portions were transferred back to the 2 liter reactor and to it was added L-tartaric acid (24.77 g, 0.165 moles, 1.1 equivalents) dissolved in acetone (354 ml, about 7 volumes) and water (44 mL, about 1 volume). The reaction mixture was agitated and heated at about 38 C. overnight. The resultant slurry was cooled to 0 C.-5 C., granulated for 1 hour, then filtered. The solids were washed with 100 ml of cold acetone and then dried in vacuo at 40 C.-50 C. for 16 hours to afford 51.86 g (87.9% yield) of the title compound of Step D.

The synthetic route of 193274-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Busch, Frank R; Chiu, Charles K; Meltz, Clifford N; Post, Ronald J; Rose, Peter R; US2002/2283; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 108724-09-0, name is 7-Bromothiazolo[4,5-c]pyridine, the common compound, a new synthetic route is introduced below. name: 7-Bromothiazolo[4,5-c]pyridine

The mixture of 6-(2-amino-5-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2- yl)pyridin-3-yl)-3,4-dihydroisoquinolin-1 (2H)-one (2-24, 68 mg, 0.186 mmol), 7- bromothiazolo[4,5-cjpyridine (2-124, 40 mg, 0.186 mmol), K3P04 (79 mg, 0.372mmo1), Pd(PPh3)2C12(13 mg, 0.0018 mmol)in THF(2 mL), and H20 (0.1 mL)was stirred at 65C for 16 h under N2 atmosphere. Upon reaction completion, the resulting mixture was filtered and concentrated under reduced pressure. The resulting residue was purified by prep-HPLC (C18 column, CH3CN/H20, containing 0.05% NH4HCO3) to get title compound 1-56 (white solid, 7 mg, 10 %). LCMS: 374 [M + Hj HPLC: 100% (254 nm); ?H NMR (400 MHz, DMSO-d6) oe 9.58 (s, 1H), 9.31 (s, 1H), 8.73 (s, 1H), 8.43 (d, J= 2.4 Hz, 1H), 7.97 (s, 1H), 7.94 (d, J 7.8 Hz, 1H), 7.79 (d, J 2.3 Hz, 1H), 7.52 (d, J= 9.4 Hz, 2H), 6.22 (s, 2H), 3.42 (s, 2H), 2.97 (t, J 6.4 Hz, 2H).

The synthetic route of 108724-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; FONDAZIONE CENTRO SAN RAFFAELE; GRAY, Nathanael S.; BUHRLAGE, Sara; ANDERSON, Kenneth; COTTINI, Francesca; TONON, Giovanni; (288 pag.)WO2016/161145; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1095823-39-4, 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 1095823-39-4, name is 5-Chloro-4-(trifluoromethyl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A 20 mL vial was charged with compound G.4 (191.8 mg, 0.65 mmol), CH2Cl2 (3.0 mL), a 2.0 M solution of oxalyl chloride in CH2Cl2 (390 muL), and DMF (10.0 muL, 0.129 mmol). The reaction mixture was stirred for 15 minutes at room temperature, then concentrated in vacuo and the resultant residue was taken up in acetonitrile (3.0 mL). To this solution was added a solution of compound G.5 (129 mg, 0.65 mmol) and pyridine (0.5 mL, 0.006 mol) in acetonitrile (1.5 mL). The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography (SiO2, 0-30% EtOAc/CH2Cl2) to give compound G.6 in 49% yield. LCMS: m/z = All [M+l].

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 1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; CHUAQUI, Claudio; COSSROW, Jennifer; DOWLING, James; GUAN, Bing; HOEMANN, Michael; ISHCHENKO, Alexey; JONES, John, Howard; KABIGTING, Lori; KUMARAVEL, Gnanasambandam; PENG, Hairuo; POWELL, Noel; RAIMUNDO, Brian; TANAKA, Hiroko; VAN VLOTEN, Kurt; VESSELS, Jeffrey; XIN, Zhili; WO2010/78408; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1796-84-5, 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 1796-84-5 as follows.

4-Ethoxy-3-nitropyridine, hydrochloride (14.5 g, 70.8 mmol) in ethyl acetate was washed twice with 1 N NaHCO3. The organic layer was dried over MgS04, filtered and the solvent evaporated under reduced pressure to give 11.8 g of a light tan solid. The free-amine (11.8 g, 69.9 mmol) and cyclopropanemethylamine (5.00 g, 70.3 mmol) in EtOH were heated at 80 C in a sealed tube for 12 h. After allowing to warm to RT, the solvent was removed under reduced pressure to give a yellow oil. Flash chromatography (silica gel, hexanes then hexanes/Et2O (1: 1: 1) then Et2O/CH2CI2 (1: 1) then CH2CI2) gave 13.1 g of the desired material. MS (ES) m/z 194.2 [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,1796-84-5, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/46678; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 3430-18-0, 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 3430-18-0, name is 2,5-Dibromo-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Method 3; Preparation of 6-bromo-5-methvmicotmaldehvde; 2,5-Dibromo-3-picoline (5.1 g, 20.30 mmol) in tetrahydrofuran (25 ml) was added dropwise to a 2M solution of isopropylmagnesium chloride (10.7 ml, 21.3 mmol) in tetrahydrofuran at 0 0C. The solution was stirred for 2 hours at 0 0C and then for 1 hour at ambient temperature. A solution of 4-formylmorpholine (2.1 ml, 20.3 mmol) in tetrahydrofuran (25 ml) was added dropwise and the solution stirred at ambient temperature for 1 hour. The solution was poured into water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulphate, filtered and the solution concentrated under reduced pressure. The residue was purified by flash chromatography, eluting with 10 % ethyl acetate in isohexane, to give the title compound (3.0 g, 74 %); NMR Spectrum: (DMSO-d6) 2.44 (s, 3H), 8.19 (s, IH), 8.73 (s, IH), 10.09 (s, IH).

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 3430-18-0, 2,5-Dibromo-3-methylpyridine.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/71956; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem