Day: September 22, 2021

Adding a certain compound to certain chemical reactions, such as: 67346-74-1, 3-Ethynylpyridin-2-amine, 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, Safety of 3-Ethynylpyridin-2-amine, blongs to pyridine-derivatives compound. Safety of 3-Ethynylpyridin-2-amine

To a mixture of (6-(4-fluoro-phenoxy)-pyridin-3-yl)-acetohydroximoyl chloride (25 mg) described in Manufacturing Example 75-1-4 and tetrahydrofuran (1 mL) were added 3-ethynyl-pyridin-2-ylamine (6.0 mg, 0.051 mmol) described in Manufacturing Example 1-2-3 and triethylamine (21 muL, 0.15 mmol), which was stirred for 5 hours at 55 C. The reaction mixture was cooled to room temperature and water was added thereto at that temperature, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate_heptane=2:1) to obtain the title compound (5.9 mg, 32%). 1H-NMR Spectrum (CDCl3) delta (ppm): 4.02 (2H, s), 5.41 (2H, br s), 6.27 (1H, s), 6.73 (1H, dd, J=4.8, 7.7 Hz), 6.90 (1H, d, J=8.4 Hz), 7.06-7.12 (4H, m), 7.62 (1H, dd, J=2.6, 8.4 Hz), 7.71 (1H, dd, J=1.7, 7.6 Hz), 8.13 (1H, d, J=2.6 Hz), 8.16 (1H, dd, J=1.7, 4.9 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,67346-74-1, 3-Ethynylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/105904; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69950-65-8, Methyl 6-formyl-2-pyridinecarboxylate, 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, Product Details of 69950-65-8, blongs to pyridine-derivatives compound. Product Details of 69950-65-8

Methyl 6-[hydroxy[6-methoxy-2-phenyl-7-(trimethylsilyl)pyrazolo[1,5-a]pyridin-3-yl]methyl]pyridi ne-2-carboxylate n-Butyllithium (0.5 mL, a 2.6 mol/L n-hexane solution) was added to a tetrahydrofuran solution (2.8 mL) of 3-bromo-6-methoxy-2-phenyl-7-(trimethylsilyl)pyrazolo[1,5-a]pyridine (410 mg) at -78C under an argon atmosphere, and then the mixture was stirred at -78C for 30 minutes. A tetrahydrofuran solution (2.8 mL) of methyl 6-formylpyridine-2-carboxylate (360 mg) was added to the obtained mixture at -78C, and then the mixture was stirred at room temperature for 1 hour. A saturated ammonium chloride aqueous solution was added to the reaction mixture and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was evaporated and then the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 4:1) to obtain a title compound as yellow liquid (303 mg). 1H-NMR (400 MHz, CDCl3) delta 0.53 (9H, s), 3.77 (3H, s), 4.07 (3H, s), 5.35 (1H, d, J = 2.4 Hz), 6.31 (1H, d, J = 2.4 Hz), 6.87 (1H, d, J = 9.7 Hz), 7.04 (1H, d, J = 9.7 Hz), 7.28 (1H, d, J = 7.9 Hz), 7.40 (1H, tt, J = 7.9, 1.8 Hz), 7.47 (2H, t, J = 7.9 Hz), 7.72 (1H, t, J = 7.9 Hz), 7.87-7.91 (2H, m), 8.04 (1H, d, J = 7.9 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69950-65-8, Methyl 6-formyl-2-pyridinecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; Kissei Pharmaceutical Co., Ltd.; SETO, Shigeki; UMEI, Kentaro; NISHIGAYA, Yosuke; TANIOKA, Asao; KONDO, Tatsuhiro; KONDO, Atsushi; TATANI, Kazuya; KAWAMURA, Naohiro; EP2669285; (2013); A1;,
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. 133627-47-1, name is N-(2-Chloro-4-methylpyridin-3-yl)-2-(cyclopropylamino)nicotinamide. A new synthetic method of this compound is introduced below., Recommanded Product: 133627-47-1

EXAMPLE 5 Preparation of 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (Nevirapine) Using sodium Hexamethyldisilazane A reaction flask equipped with a magnetic stirrer, temperature controller thermodouple, addition funnel and condenser with an oil bubbler for exclusion of ambient air was inerted with nitrogen and charged with 3.02 g (0.010 mol) of N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide from Example 4 and 30 ml of anhydrous THF. A 40% solution of sodium hexamethyldisilazane in THF (12.7 ml, 0.025 mol) was added dropwise maintaining the temperature of the reaction mixture at no more than 30 C. When the addition of the NaHMDS solution was completed, the reaction mixture was heated to reflux temperature (about 63-66 C.).When the reaction was completed (HPLC analysis), the mixture was cooled to ambient temperature.The reaction mixture was treated with 1.55 g (0.050 mol) of methanol and 0.45 g of water (0.025 mol).The mixture was concentrated on a rotary evaporator at 25-30 in.Hg with a 50-60 water bath temperature.The residual product weighing 4.44 g was triturated with 50 ml of water and the PH 10-12 solution was acidified to PH 3 by adding 10% HCl solution.The solid product was collected by filtration and the filter cake rinsed three times with 10 ml portions of water.The filter cake was dried in a vacuum oven at 50-60 C. to obtain nevirapine.

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, 133627-47-1, N-(2-Chloro-4-methylpyridin-3-yl)-2-(cyclopropylamino)nicotinamide.

Reference:
Patent; Boehringer ingelheim Chemicals, Inc.; US2004/2603; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 67058-76-8, Adding some certain compound to certain chemical reactions, such as: 67058-76-8, name is 3-Bromo-1H-pyrrolo[2,3-c]pyridine,molecular formula is C7H5BrN2, 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 67058-76-8.

Sodium hydride (60 % in mineral oil) (217 mg) was added to a stirred solution of 3-bromo- 1 /-/-pyrrolo[2,3-c]pyridine (535 mg) in DMF (5 ml) that had been cooled in an ice bath to 0 C and placed under nitrogen. The mixture was stirred for 30 min, until hydrogen evolution ceased, and then 4-nitrobenzenesulfonyl chloride (662 mg) was added. The mixture was stirred at 0 C for 1 hour. The mixture was then warmed to RT and stirred for a further 30 min. The solution was poured into stirring water (10 ml) and rapidly stirred for 15 min. The resulting brown solid was collected by filtration, washed with water and dried in a vacuum oven at 50 C to give a yellow solid. This crude material was purified by FlashMaster II. The residue was dissolved in DCM:methanol (1 :1 ) and pre adsorbed onto silica. This was added to the top of a 20 g silica SPE cartridge that was subsequently eluted with 0 – 50 % ethyl acetate:cyclohyexane over 40 min. The product-containing fractions were combined and the solvent removed in vacuo to give the title compound, 233 mg as a white solid. LCMS (Method B): Rt = 1.01 min, MH+ = 384.

According to the analysis of related databases, 67058-76-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; BALDWIN, Ian, Robert; DOWN, Kenneth, David; FAULDER, Paul; GAINES, Simon; HAMBLIN, Julie, Nicole; LE, Joelle; LUNNISS, Christopher, James; PARR, Nigel, James; RITCHIE, Timothy, John; ROBINSON, John, Edward; SIMPSON, Juliet, Kay; SMETHURST, Christian, Alan, Paul; WO2011/67364; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14432-12-3, 4-Amino-2-chloropyridine, 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, 14432-12-3, blongs to pyridine-derivatives compound. name: 4-Amino-2-chloropyridine

Preparation 7: 2-Chloro-5-iodo-pyridin-4-ylamine N-lodosuccinimide (24.75 g, 110.0 mmol) was added to a solution of 2-chloro-pyridin-4-ylamine (12.85 g, 100.0 mmol) in acetonitrile (400 mL) and the mixture stirred and held at reflux overnight. Upon cooling to room temperature the solvent was removed in vacuo and residue partitioned between EtOAc (250 mL), saturated sodium thiosulfate (100 mL) andwater (250 mL). The organic layer was separated, washed with water (2 >< 250 mL), separated and the solvent removed in vacuo to afford an orange oil that was subjected to column chromatography on silica. Gradient elution with 30-50% EtOAc in petrol afforded a pale orange solid that was rinsed with 25% EtOAc in petrol (80 mL). Solids were collected by filtration and sucked dry to afford the title compound (7.32 g) as an off-white solid. Themother liquors were concentrated to dryness in vacuo and the residues subjected to columnchromatography on silica. Elution with 30-50% EtOAc in petrol afforded further pure material(1.90 g). Combined yield : (9.22 g, 36%) 1H NMR (DMSO-d6) 8.20 (1H, 5), 6.64 (1H, 5), 6.50(2H, br 5). MS: [M+H] 255. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14432-12-3, its application will become more common. Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CHESSARI, Gianni; JOHNSON, Christopher Norbert; PAGE, Lee William; BUCK, Ildiko Maria; DAY, James Edward Harvey; HOWARD, Steven; SAXTY, Gordon; MURRAY, Christopher William; WO2014/60770; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 10592-27-5, 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.10592-27-5, name is 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H8N2, molecular weight is 120.15, as common compound, the synthetic route is as follows.

To a solution of sulfurisocyanatidic chloride (22 mg, 0.16 mmol) in DCM (2 mL) was added a solution of Intermediate GW-18.3 (70 mg, 0.15 mmol) and DIPEA (0.05 mL, 0.3 mmol) in DCM (2 mL) in an ice-water bath and the reaction mixture was stirred for 2 min. Then a solution of 2,3-dihydro-lH-pyrrolo[2,3-b]pyridine (28.0 mg, 0.233 mmol) in DCM (2 mL) was added, followed by DIPEA (0.11 mL, 0.62 mmol) and the reaction mixture was stirred for 2 min, the bath was removed and the stirring was continuted at rt for 2 h. The reaction mixture was concentrated and purified by preparative HPLC to afford the title compound (19.4 mg). LC-MS retention time = 3.37 min; m/z = 603.20 [M+H]+ (Column: Phenomenex C18 2.0 X 50 mm, 3 muetaiota particles; Mobile Phase A: 10% MeOH-90% H2O-0.1% TFA; Mobile Phase B: 90% MeOH-10% H2O-O. /0 TFA; Temperature: 40 C; Gradient: 0-100% B over 4 min, then a 1-min hold at 100% B; Flow: 0.8 mL/min; Detection: UV at 220 nm).

The chemical industry reduces the impact on the environment during synthesis 10592-27-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 84249-14-9, 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.84249-14-9, name is 2-Amino-4-bromopyridine, molecular formula is C5H5BrN2, molecular weight is 173.0106, as common compound, the synthetic route is as follows.

To a solution of 4-bromopyridin-2-amine (5.0 g, 29.07 mmol) in dichloromethane (50 mL) cooled to 0 C was added pyridine (3.5 mL, 43.4 mmol) and the solution was stirred for 10 min. Acetyl chloride (2.1 mL, 29.5 mmol) was added. The reaction mixture was allowed to stir at 0 C for 30 min. Then the reaction mixture was allowed to warm to RT and stirred for 1 h. The reaction mixture was diluted with brine (50 mL). The aqueous layer was extracted with dichloromethane (3 x 200 mL). The organic layer was dried over Na2S04, filtered and concentrated under reduced to afford the title compound (4.1 g, 19.2 mmol, 66%> yield) as a light yellow solid. LCMS (ESI) m/e 215.0 [(M+H)+, calcd for C7H8BrN20, 215.0]; LC/MS retention time (method F): tR = 1.53 min.

Statistics shows that 84249-14-9 is playing an increasingly important role. we look forward to future research findings about 2-Amino-4-bromopyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DZIERBA, Carolyn Diane; BRONSON, Joanne J.; MACOR, John E.; DASGUPTA, Bireshwar; NARA, Susheel Jethanand; VRUDHULA, Vivekananda M.; PAN, Senliang; HARTZ, Richard A.; RAJAMANI, Ramkumar; (199 pag.)WO2016/22312; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 74764-17-3, 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 74764-17-3, name is N1-(Pyridin-2-yl)ethane-1,2-diamine. This compound has unique chemical properties. The synthetic route is as follows.

Step 6 (3S)-8-Amino-9-fluoro-2,3-dihydro-7-oxo-3-phenylmethyl-10-[2-(2-pyridylamino)ethylamino]-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid A mixture of (3S)-8-Amino-9,10-difluoro-2,3-dihydro-7-oxo-3-phenylmethyl-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid (76.9 mg, 0.207 mmol), 2-(2-pyridylamino)ethylamine (41.8 mg, 0.303 mmol), and triethylamine (42.1 muL, 0.302 mmol) in DMSO (1.5 mL) was stirred at 100 C. for 3 h. The reaction mixture was poured into ice-water and the resulting precipitates were collected by filtration. Recrystallization of the filtered precipitates from CH2Cl2-EtOH gave (3S)-8-amino-9-fluoro-2,3-dihydro-7-oxo-3-phenylmethyl-10-[2-(2-pyridylamino)ethylamino]-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid (55.4 mg, 55%) as a yellow powder. 1H NMR (400 MHz, CDCl3) delta 2.98-3.09 (2H, m), 3.71 (2H, br), 3.82 (2H, br), 3.97 (1H, d, J=11.0 Hz), 4.20 (1H, t, J=7.9 Hz), 4.33 (1H, d, J=11.0 Hz), 4.71 (1H, br), 5.75 (1H, br), 6.25 (2H, br), 6.44 (1H, d, J=7.9 Hz), 6.60 (1H, dd, J=6.7, 5.5 Hz), 7.11 (2H, d, J=6.7 Hz), 7.31-7.43 (4H, m), 8.07 (1H, s), 8.69 (1H, dd, J=5.5, 1.5 Hz), 15.1 (1H, s). HRESIMS (+): 490.19342 (calcd for C26H25FN5O4, 490.18906). [alpha]D27-204 (c 0.313, CHCl3).

According to the analysis of related databases, 74764-17-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cociorva, Oana; Li, Bei; Szardenings, Katrin; Fukuda, Yasumichi; Nomura, Masahiro; Seto, Shigeki; Yumoto, Kazuhiro; Okada, Kyoko; Nakamura, Ayako; US2007/254866; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 17282-03-0 ,Some common heterocyclic compound, 17282-03-0, molecular formula is C6H5BrClN, 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.

Synthesis 53 [5-(2-Chloro-5-methyl-pyridi -3-yl)-thiazol-2-yl]-propyl-carbamic acid tert-butyl ester 3-tert-Butyl-1-propyl-1-[5-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-thiazol-2-yl]-urea (1 mmol, 0.37 g) 2-chloro-3-bromo-5-methylpyridine (1 mmol, 0.20 g), potassium carbonate (2 mmol, 0.27 g) and bis(triphenylphosphine) palladium(ll)dichloride (0.050 mmol, 0.035 g) were weighed into a microwave vial and treated with dioxane (1.5 mL) and water (0.5 mL). The reaction mixture was heated at 130 C for 15 minutes in a microwave reactor. The reaction mixture was diluted with water (40 mL), extracted with DCM (2×30 mL) and passed through a phase separation cartridge. The organics were evaporated to a brown oil. This was purified by flash column chromatography 1 :9 ethyl acetate cyclohexane to yield the title compound as a pale yellow oil. LCMS, analytical method 2, TR=6.22 mins, 70%, Ml+H=368.

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. 17282-03-0, 3-Bromo-2-chloro-5-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHARLES, Mark David; BROOKFIELD, Joanna Lola; EKWURU, Chukuemeka Tennyson; STOCKLEY, Martin Lee; WO2015/25172; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 22245-83-6, 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 22245-83-6, name is 3-(Trifluoromethyl)pyridin-2-ol. This compound has unique chemical properties. The synthetic route is as follows.

5-iodo-3-trifluoromethyl-2-pyridinol C 800C, 2h I>80%[0070] 3-trifluoromethyl-2-pyridinol (25 g, 153.3 mmol) is dissolved in anhydrousCH3CN (150 rnL) and DMF (150 rnL). N-iodosuccinimide (34.5 g, 153 mmol) is then added. The reaction mixture is stirred at 80 0C for 2 hours and cooled to room temperature. Aqueous 1 M NaHCO3 (150 mL) is then added to the cooled mixture. After stirring for 5 min, the solvents are evaporated to dryness. Water is added and the aqueous phase is extracted (x2) with dichloromethane. The organic phase is then evaporated and the desired product is recrystallized in water to afford 36.2 g (81 %) of a white powder.[0071] 1H NMR (500 MHz, CDCl3) delta 7.85 (d, J= 2.3, IH); 7.98 (d, J= 2.3, IH),13.41 (br s, IH); 13C NMR (250 MHz CDCl3) delta 63.0, 121.4 (q, JC-F= 272.3 Hz), 122.2 (q, JC- F= 31.6 Hz), 144.4, 148.1 q, (JC-F= 5.0 Hz), 160.1.

According to the analysis of related databases, 22245-83-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; WO2008/119015; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem