Tag: M.W:100-200

Electric Literature of 60781-83-1 ,Some common heterocyclic compound, 60781-83-1, molecular formula is C11H10N2, 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.

To a RT solution of 4-phenylpyridin-2-amine (8 mg, 0.044 mmol) in THF (0.5 mL) was added NaH (2 mg, 0.033 mmol, 60% in mineral oil), and the mixture was stirred at RT for 30 min. Intermediate 1 (10 mg, 0.022 mmol) in THF (0.2 mL) was added and the reaction mixture was stirred at RT for 4 h, after which THF (0.8 mL)/H20 (0.4 mL)/ MeOH (0.4 mL) and LiOH.H20 (5 mg, 0.11 mmol) were added and the mixture was stirred overnight at RT. Volatiles were removed in vacuo and the residue was diluted with H20 (5 mL); the mixture was adjusted with 1N aq. HC1 to pH ~5 and extracted with EtOAc (3 x 5 mL). The combined organic extracts were washed with brine (2 mL), dried (MgSCL), and concentrated in vacuo. The crude product was purified by preparative LC/MS: Column: Waters XBridge Cl 8, 19 x 200 mm, 5-pm particles; Guard Column: Waters XBridge C18, 19 x 10 mm, 5-pm particles; Mobile Phase A: 5:95 MeCN:H20 with 0.1% TFA; Mobile Phase B: 95:5 MeCN:H20 with 0.1% TFA; Gradient: 50-90% B over 20 min, then a 5-min hold at 100% B; Flow: 20 mL/min. The combined fractions containing the desired product were concentrated in vacuo by centrifugal evaporation to give the title compound (3.1 mg, 6.0 pmol, 27 % yield). LCMS, [M + H]+ = 499.3. NMR (500 MHz, DMSO-de) d 8.05 (d, ,7=5.6 Hz, 1H), 7.87 (d, ,7=8.5 Hz, 1H), 7.51 (d, ,7=8.6 Hz, 1H), 7.46 – 7.40 (m, 2H), 7.38 – 7.32 (m, 3H), 6.85 – 6.80 (m, 2H), 5.04 (d, J=5.5 Hz, 2H), 4.79 – 4.72 (m, 1H), 4.14 (s, 3H), 2.59 – 2.54 (m, 1H), 2.39 (s, 3H), 2.01 – 1.45 (m, 8H). hLPAi IC5o = 32 nM.

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. 60781-83-1, 4-Phenylpyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; WANG, Ying; CHENG, Peter Tai Wah; SHI, Jun; TAO, Shiwei; CORTE, James R.; FANG, Tianan; LI, Jun; KENNEDY, Lawrence J.; KALTENBACH, III, Robert F.; JUSUF, Sutjano; (316 pag.)WO2019/126093; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1256805-54-5, 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. 1256805-54-5, name is 6-Chloro-4-methoxypyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 6-chloro-4-methoxypyridin-3-ylamine (0.95 mmol, 160 mg) in dichloromethane (1 mL) and pyridine (2 mmol, 165 microliter) (3,4-dichlorophenyl)- methanesulfonyl chloride ((275 mg, 0.95 mmol) was added and the mixture was stirred overnight and then concentrated on a rotary evaporator. To the residue ethanol (99.5 %, 5 mL) and NaOH (1 M, 2 mL) were added and the mixture was heated at 60 C until all material went into solution (took less than 5 min). The mixture was cooled, water (5 mL) and glacial acetic acid were added to pH 3-4 (checked with pH sticks). The precipitate was collected by filtration and dried to afford the intermediate N-(6-chloro-4-methoxy- pyridin-3-yl)-3,4-dichlorophenyl-methanesulfon-amide which was dissolved in dichloromethane (2 mL), cooled on an ice-bath and boron tribromide (1M solution in dichloromethane, 2 mmol, 2 mL) was added dropwise. The mixture was stirred at room temperature overnight. The mixture was then partitioned between dichloromethane and aqueous sodium hydroxide at pH 13. The aqueous phase was collected, pH was adjusted to approx. 3-4 with acetic acid and the mixture was extracted with ethylacetate (20 mL). The organic phase was collected and evaporated and the residue was crystallized from methanol/water to afford the title compound (158 mg, 43%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1256805-54-5, 6-Chloro-4-methoxypyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; ACTIVE BIOTECH AB; FRITZSON, Ingela; LIBERG, David; EAST, Stephen; MACKINNON, Colin; PREVOST, Natacha; WO2014/184234; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 100155-73-5, Adding some certain compound to certain chemical reactions, such as: 100155-73-5, name is 1-(2-Pyridyl)-1-propylamine,molecular formula is C8H12N2, 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 100155-73-5.

Example 45 7-[(4′-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl-pyridin-2-ylmethyl-amide The title compound was provided by the reaction of 7-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid and ethyl-pyridin-2-ylmethyl-amine in a procedure analogous to Examples 1-34. MS (APCI) 555 (M+1)+; 553 (M-1)-

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. 100155-73-5, 1-(2-Pyridyl)-1-propylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer, Inc.; US6369075; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 709652-82-4, 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 709652-82-4 as follows.

Example 2; 5-bromo-2-chloropyridine-3-carbonitrile (3) ; [00141] Compound 2 was dissolved in cone. HCl at O2C, to which 1.1 equivalent of NaNO2 in H2O was added dropwise. Precipitation was formed. The white solid was filtered off, which gave the title compound 3. Overall yield was 70%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,709652-82-4, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/59219; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 4021-07-2, 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 4021-07-2 as follows.

Weighing 3-methylpyridine-2-carboxylic acid (56.7 mg, 0.3 mmol), sodium hydroxide (16.0 mg, 0.15 mmol), TBAC (26.3 mg, 0.45 mmol), DTBP (165 muL, 0.9 mmol) into 25 mL of Schlenk 25 mL of Schlenk, Then CH3CN (0.5 mL) was added and placed in a 50 °C oil bath for 20 h. After completion of the reaction, the solvent was removed under reduced pressure and eluted with petroleum ether / ethyl acetate.The solvent was separated on a silica gel column, The yield of 2-chloro-3-methylpyridine was 70percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4021-07-2, its application will become more common.

Reference:
Patent; Dalian University of Technology; Feng Xiujuan; Zhang Xitao; Zhang Haixia; Bao Ming; (27 pag.)CN108586334; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 39998-25-9, 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. 39998-25-9, name is Methyl 2-(pyridin-3-yl)acetate, molecular formula is C8H9NO2, 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.

Into a 500-mL flask to which a nitrogen gas introduction tube, thermometer, and Dimroth condenser had been attached were introduced 21.29 g (0.141 mol) of the methyl 3-pyridylacetate obtained above and 250 mL of anhydrous methanol. The contents were stirred at room temperature. The atmosphere in the flask was replaced with nitrogen, and 15.62 g (0.372 mol) of sodium borohydride was added to the contents little by little. The resultant mixture was heated and reacted for further 3.5 hours with refluxing. Thereafter, the liquid reaction mixture was cooled to room temperature, and 100 mL of water was added thereto to hydrolyze the excess sodium borohydride remaining unreacted. The methanol was distilled away under vacuum. Thereafter, an extraction operation using 100 mL of chloroform was conducted twice, and the resultant organic phase was washed with 100 mL of saturated aqueous sodium chloride solution and dried by adding anhydrous sodium sulfate thereto. The anhydrous sodium sulfate was removed by decantation. Thereafter, vacuum distillation was conducted to obtain 12.59 g (0.102 mol) of 3-pyridylethanol.

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 39998-25-9, Methyl 2-(pyridin-3-yl)acetate.

Reference:
Patent; Mitsubishi Chemical Corporation; EP2390243; (2011); 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. 582303-10-4, name is (2,6-Dimethylpyridin-3-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

To a mixture of tri-n-butylphosphine (0.240 mL) , (2,6- dimethylpyridin-3-yl) methanol (92 mg) , methyl ( 6-hydroxy-4 , 7- dimethyl-l-benzofuran-3-yl) acetate (150 mg) and THF (6.0 mL) was added ADDP (242 mg) at room temperature. The mixture was stirred at room temperature overnight under nitrogen atmosphere. The mixture was concentrated. To the residue was added IPE and the precipitate was filtered off and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (163.9 mg) . XK NMR (300 MHz, CDC13) delta 2.33 (3H, s) , 2.54 (3H, s) , 2.55 (3H, s), 2.58 (3H, s), 3.73 (3H, s) , 3.80 (2H, d, J = 1.1 Hz), 5.04 (2H, s), 6.68 (1H, s) , 7.02 (1H, d, J = 7.6 Hz), 7.51 (1H, s) , 1.63 (1H, d, J = 7.9 Hz)

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, 582303-10-4, (2,6-Dimethylpyridin-3-yl)methanol.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKAKURA, Nobuyuki; BANNO, Yoshihiro; TERAO, Yoshito; OCHIDA, Atsuko; MORIMOTO, Sachie; KITAMURA, Shuji; TOMATA, Yoshihide; YASUMA, Tsuneo; IKOMA, Minoru; MASUDA, Kei; WO2013/125732; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 832735-60-1, 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 832735-60-1 as follows.

Example 444 (1538) N-tert-Butyl-3?-fluoro-4?[1,2,4]triazolo[4,3-a]pyridin-7-ylbiphenyl-2-sulfonamide (1539) To a 20 mL vial were added N-(tert-butyl)-3?-fluoro-4?-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1?-biphenyl]-2-sulfonamide (45 mg, 0.10 mmol), 7-bromo-[1,2,4]triazolo[4,3-a]pyridine (21 mg, 0.10 mmol) K2CO3 (29 mg, 0.21 mmol), Pd(dppf)Cl2.CH2Cl2 (4 mg, 0.005 mmol), and a stir bar. The vial was sealed with a teflon lined cap and the vial sparged with N2. The vial was then charged with freshly sparged DMSO (2 mL) and stirred for 16 hours at 80 Celsius. The reaction mixture was then cooled to rt, filtered, and purified by HPLC to give the title compound (30 mg, 53%). MS (ESI): mass calcd. for C22H21FN4O2S, 424.14; m/z found, 425.1 [M+H]+. 1H NMR (400 MHz, CD3OD) delta 9.40 (s, 1H), 8.79 (s, 1H), 8.20-8.11 (m, 2H), 7.77 (m, 1H), 7.70-7.57 (m, 3H), 7.47-7.38 (m, 3H), 1.10 (5, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,832735-60-1, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Bacani, Genesis M.; Eccles, Wendy; Fitzgerald, Anne E.; Goldberg, Steven D.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Lee-Dutra, Alice; Liu, Jing; McClure, Kelly J.; Meduna, Steven P.; Pippel, Daniel J.; Rosen, Mark D.; Sales, Zachary S.; US2015/259357; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 3279-76-3, 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. 3279-76-3, name is 6-Methylpyridin-2(1H)-one, molecular formula is C6H7NO, 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.

PREPARATION 133 2-Methoxy-6-methylpyridine Trimethyloxonium tetrafluoroborate (10.0 g, 67.6 mmol) was added portionwise to a suspension of 6-methylpyridin-2-one (7.3 g, 67.0 mmol) in dichloromethane (100 ml), and once addition was complete, the reaction was stirred at room temperature for 24 hours. Dichloromethane (50 ml) and aqueous sodium hydroxide solution (50 ml, 2N) were added and the layers separated. The aqueous phase was extracted with dichloromethane (2*50 ml), the combined organic solutions washed with brine (50 ml), dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel, using an elution gradient of pentane: dichloromethane (66:34 to 0:100) to afford the title compound (2.25 g, 27%) as a colourless oil. delta (CDCl3): 2.49 (3H, s), 3.90 (3H, s), 6.38-6.73 (2H, m), 7.23-7.40 (1 H, br d).

According to the analysis of related databases, 3279-76-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US6251904; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54916-65-3, 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. 54916-65-3, name is 5-Chloro-2-methoxynicotinic acid, molecular formula is C7H6ClNO3, 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-Chloro-2-methoxy-pyridine-3 -carboxylic acid (182 mg, 0.97 mmol) and 6-[4-[(lS)- 2,2,2-trifluoro-l-methyl-ethyl]-l,2,4-triazol-3-yl]pyridin-2-amine (250 mg, 0.97 mmol) were dissolved in triethylamine (1.35 mL, 9.72 mmol). Propylphosphonic anhydride (> 50 wt % in EtOAc, 1.0 mL) was added and the reaction was heated at 80 C for 3 h. The reaction was cooled to rt, quenched by addition of MeOH (5 mL) and stirred for 1 h. The resulting solid was filtered and dried under vacuum to give the title compound (200 mg, 48 %) as a white solid. 1H NMR (400 MHz, CDCI3) d 10.37 (s, 1H), 8.58 (d, 7=2.51 Hz, 1H), 8.43 – 8.49 (m, 2H), 8.31 (d, 7=2.51 Hz, 1 H), 8.16 (dd, 7=0.75, 7.78 Hz, 1H), 7.95 (t, 7=7.91 Hz, 1H), 6.71 (quin, 7=7.22 Hz, 1H), 4.19 (s, 3H), 1.82 (d, 7=7.28 Hz, 3H). MS (ESI): 427.0 [M + H]+.

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 54916-65-3, 5-Chloro-2-methoxynicotinic acid.

Reference:
Patent; BIOGEN MA INC.; GONZALEZ LOPEZ DE TURISO, Felix; DECHANTSREITER, Michael; XIN, Zhili; JONES, John, H.; HIMMELBAUER, Martin; (0 pag.)WO2020/6031; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem