Tag: M.W:100-200

Reference of 1346575-64-1, 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.1346575-64-1, name is 3-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-one, molecular formula is C10H16N2O, molecular weight is 180.25, as common compound, the synthetic route is as follows.

Example 11l-(l-Methylethyl)- V-[(6-methyl-2-oxo-4-propyl-l,2-dihydro-3-pyridinyl)methyl]-6-(4- pyridinyl)-l -pyrazolo[3,4-6]pyridine-4-carboxamidel-(l-Methylethyl)-6-(4-pyridinyl)-l H-pyrazolo [3, 4-b]pyridine-4-carboxylic acid (150 mg, 0.531 mmol), 3-(aminomethyl)-6-methyl-4-propyl-2(lH)-pyridinone (1 15 mg, 0.531 mmol), EDC (122 mg, 0.638 mmol), HOAt (72.3 mg, 0.531 mmol), and N- methylmorpholine (0.233 mL, 2.12 mmol) were suspended in DMF (5 mL) and stirred at room temperature overnight, water was added to the reaction mixture, and the contents were filtered. The filter cake was washed with addional water (2x). The crude solid was purified by reverse phase HPLC (mobile phase: 10-30% ACN in H20, 0.1% TFA). The isolated solid was then neutralized with saturated NaHC03, and washed with EtOAc (5 x 15 mL). The combined organic layers were dried over Na2S04, filtered, and concentrated in vacuo to afford the title compound as an off-white solid, 0.060 g (24%). LCMS E-S (M+H) = 445.3. 1H NMR (400 MHz, DMSO-d6) ? ppm 0.84 – 0.92 (m, 3 H), 1.47 – 1.54 (m, 2 H), 1.57 (d, J=6.82 Hz, 6 H), 2.14 (s, 3 H), 2.48 – 2.52 (m, 2 H), 4.42 – 4.49 (m, 2 H), 5.33 – 5.43 (m, 1 H), 5.90 – 5.96 (m, 1 H), 8.28 – 8.37 (m, 3 H), 8.44 – 8.48 (m, 1 H), 8.82 – 8.87 (m, 2 H), 8.99 – 9.04 (m, 1 H), 11.58 (s, 1 H).

Statistics shows that 1346575-64-1 is playing an increasingly important role. we look forward to future research findings about 3-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-one.

Reference:
Patent; GLAX0SMITHKLINE LLC; BURGESS, Joelle, Lorraine; JOHNSON, Neil, W.; KNIGHT, Steven, David; LAFRANCE, Louis, Vincent, III; MILLER, William, H.; NEWLANDER, Kenneth, Allen; ROMERIL, Stuart, Paul; ROUSE, Meagan, B.; SUAREZ, Dominic; TIAN, Xinrong; VERMA, Sharad, Kumar; WO2013/39988; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6188-23-4, 6-Bromoimidazo[1,2-a]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, Recommanded Product: 6188-23-4, blongs to pyridine-derivatives compound. Recommanded Product: 6188-23-4

A mixture of the compound of example 1 (1.0 g, 5.08 mmol) and t-butyl 4-(5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate (1.97 g, 5.08 mmol) were treated with [1 ,1 ‘-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.124 g, 0.152 mmol) and sodium carbonate (2.15 g, 20.30 mmol) in dry dimethylformamide (100 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1.05 g (54.68 %); 1H NMR (DMSO-d6, 300 MHz): delta 1.39 (s, 9H, 3CH3), 3.44 (s, 4H, 2CH2), 3.55 (s, 4H, 2CH2), 6.95 (d, 1H, J=8.7 Hz, Ar), 7.50-7.62 (m, 3H, Ar), 7.87 (d, 1H, J=2.4 Hz, Ar), 7.90 (s, 1H, Ar), 8.46 (d, 1H, J=2.4 Hz, Ar), 8.83 (s, 1H, Ar); MS (ES+): m/e 380 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6188-23-4, 6-Bromoimidazo[1,2-a]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; GHOSH, Usha; MORE, Tulsidas; KULKARNI, Mahesh; BAJAJ, Komal; BURUDKAR, Sandeep; RIZVI, Zejah; WO2014/80241; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1174229-72-1, Ethyl 2-(6-aminopyridin-3-yl)acetate, 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, 1174229-72-1, blongs to pyridine-derivatives compound. Recommanded Product: 1174229-72-1

A 20-mL vial was charged with 4-chloro-2-(3-chlorophenyl)-6- cyclopropylpyrimidine (0.380 g, 1.43 mmol), ethyl 2-(6-aminopyridin-3-yl)acetate (0.410 g, 2.27 mmol), palladium acetate (0.016 g, 0.071 mmol), rac-BINAP (0.069 g, 0.11 mmol) and cesium carbonate (1.17 g, 3.58 mmol) in dioxane (10 mL) under argon. The reaction mixture was heated to 110 C under microwave irradiation for 1.25 h. The reaction mixture was cooled, and diluted with ethyl acetate and filtered through celite. The filtrate was washed with saturated sodium chloride (2 x 10 mL), dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on silica using hexanes/ethyl acetate (10:0 to 0: 10) as eluent to afford the title compound (0.504 g, 86%) as an off-white solid. MW = 408.88. M.p. 133-135 C. ]H NMR (DMSO- , 500 MHz) delta 10.13 (s, 1H), 8.31-8.29 (m, 1H), 8.27 (dt, / = 7.0, 1.5 Hz, 1H), 8.22 (d, / = 2.0 Hz, 1H), 7.75-7.68 (m, 2H), 7.62 (br s, 1H), 7.59-7.52 (m, 2H), 4.10 (q, / = 7.5 Hz, 2H), 3.68 (s, 2H), 2.07 (septet, / = 4.5 Hz, 1H), 1.21 (t, / = 7.0 Hz, 3H), 1.14-1.10 (m, 2H), 1.06-1.00 (m, 2H); APCI MS m/z 409 [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,1174229-72-1, its application will become more common.

Reference:
Patent; TETRA DISCOVERY PARTNERS, LLC.; GURNEY, Mark, E.; HAGEN, Timothy, J.; MO, Xuesheng; VELLEKOOP, A.; ROMERO, Donna, L.; CAMPBELL, Robert, F.; WALKER, Joel, R.; ZHU, Lei; WO2014/66659; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 677728-92-6, 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 677728-92-6, name is 2-Fluoropyridine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 24: (trans-4-{ri-(5-formylpyridin-2-yl)piperidin-4-yl1oxy|cvclohexyl)acetic acidA mixture of [trans-4-(piperidin-4-yloxy)cyclohexyl] acetic acid (0.8 g, 3.32 mmol), 3- fluoro-5-formylpyridine (0.415 g, 3.32 mmol) and sodium bicarbonate (1.67 g, 19.89 mmol) in NMP (6 ml) was heated at 110C in an oil bath over night under N2. The reaction mixture was cooled to room temperature then concentrated under vacuum. The residual was applied onto a silica gel column and eluted with acetone/dichloromethane 0-100%. This resulted in 0.28 g (24.4%) of: (trans-4-{[l-(5-formylpyridin-2-yl)piperidin-4-yl]oxy}cyclohexyl)acetic acid as a white solid. LC-MS (ES, m/z): Ci9H26N204: 346; Found: 347 [M+H]+.

According to the analysis of related databases, 677728-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTERVET INTERNATIONAL B.V.; DE VITA, Robert, J.; HONG, QingMei; LAI, Zhong; DYKSTRA, Kevin, D.; YU, Yang; LIU, Jian; SPERBECK, Donald; JIAN, Tianying; GUIADEEN, Deodial; XU-QIANG YANG, Ginger; WU, Zhicai; HE, Shuwen; TING, Pauline, C.; ASLANIAN, Robert; KUETHE, Jeffrey, T.; BALKOVEC, James, M.; KUANG, Rongze; ZHOU, Gang; WU, Heping; WO2012/164071; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 54221-96-4 ,Some common heterocyclic compound, 54221-96-4, molecular formula is C7H7NO2, 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.

6-Methoxy-2-pyridinecarboxaldehyde (1.0 mL, 8.31 mmol) and 2-naphthylamine (1.19 g,8.33 mmol) were dissolved in 25 mL of anhydrous methanol and the resulting mixture washeated at reflux temperature for 6 h. The solvent was removed under reduced pressure togive brown solids. Yield: 1.58 g (72percent). Anal. Calcd (percent) for C17H14N2O (M = 262.31 g mol?1): C,77.84; H, 5.38; N, 10.68. Found: C, 77.88; H, 5.43; N, 10.71. FT-IR (KBr, cm?1): 3439(w), 3051(w),2976(w), 2840(w), 1632(m), 1586(s), 1569(m), 1508(w), 1467(s), 1438(m), 1413(w), 1350(w),1334(m), 1321(m), 1267(s), 1229(w), 1208(w), 1167(w), 1151(m), 1120(w), 1078(w), 1032(m),985(w), 961(w), 911(w), 887(w), 860(s), 824(m), 808(s), 750(s), 734(w), 666(w), 626(w), 603(w),523(w), 504(w), 478(w), 430(w). 1H NMR (400 MHz, CDCl3): delta 8.63 (s, 1H, CH = N), 7.52?7.87(m, 7H, Naphthalene-H), 6.84?7.02 (m, 3H, Py-H3,4,5), 4.03 (s, 3H, ?OCH3) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54221-96-4, its application will become more common.

Reference:
Article; Dong, Yu-Wei; Wang, Ping; Fan, Rui-Qing; Chen, Wei; Wang, A-Ni; Yang, Yu-Lin; Journal of Coordination Chemistry; vol. 70; 11; (2017); p. 1953 – 1972;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 109-04-6 , The common heterocyclic compound, 109-04-6, name is 2-Bromopyridine, molecular formula is C5H4BrN, 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 solution of n-BuLi (15.00 mmol) in diethyl ether (30.0 mL) at78 C was added dropwise to a solution of bromopyridine(15.00 mmol) in diethyl ether (25.0 mL). The resulting solutionwasstirred at 78 C for 2 h. And then, the solution of Bu3SnCl orMe3SnCl (15.00 mmol) in THF (10.0 mL) was added dropwise andstirred at 78 C for another 3 h. The resulting deep-red solutionwas warmed to room temperature over night and a heavy precipitateformed. Hydrolysis was achieved with a saturated aqueoussolution of NH4Cl. Subsequent treatments (Et2O extraction, dryingon anhydrous Na2SO4, concentration and flash chromatography)afforded pure product.

The synthetic route of 109-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma, Gaizhi; Leng, Yuting; Wu, Yusheng; Wu, Yangjie; Tetrahedron; vol. 69; 2; (2013); p. 902 – 909;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71255-09-9, Adding some certain compound to certain chemical reactions, such as: 71255-09-9, name is 2-Methoxynicotinaldehyde,molecular formula is C7H7NO2, 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 71255-09-9.

[0706] A mixture of trans-3-(4-amino-phenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1 eq.), 2-methoxy-3-formyl-pyridine (1.05 eq.), sodium triacetoxyborohydride (3.4 eq.) and acetic acid (3.4 eq) was stirred in anhydrous 1,2-dichloroethane for 16 hours. The reaction mixture was concentrated under reduced pressure, quenched with saturated solution of sodium bicarbonate in water and concentrated again. The residue was purified by preparative HPLC (Hypersil C18, 8 mum, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield the desired products. The following two compounds were prepared according to the procedure above: trans-3-(4-[(2-methoxy-3-pyridyl)methyl]aminophenyl)-1-[4-(4-methyl-piperazino)cyclohexyl]-1H-pyrazolo [3,4-d]pyrimidin-4-amine Diacetate [0707] 1H NMR (DMSO-d6, 400 MHz) delta 8.18 (s, 1H), 8.06 (dd, 1H), 7.61 (d, 1H), 7.35 (d, 2H), 6.95 (dd, 1H), 6.69 (d, 2H), 6.51 (t, 1H), 4.60 (m, 1H), 4.26 (d, 2H), 3.94 (s, 3H), 2.64 (s, 3H), 2.6-2.2 (br, 9H), 2.13 (s, 3H), 2.05 (m, 6H), 1.91 (s, 6H), 1.46 (m, 2H); [0708] RP-HPLC (Delta Pak C18, 5 mum, 300A, 15 cm; 5%-85% acetonitrile-0.1M ammonium acetate over 20 min, 1 mL/min) Rt 12.07 min. [0709] MS: MH+ 528.

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. 71255-09-9, 2-Methoxynicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hirst, Gavin C.; Rafferty, Paul; Ritter, Kurt; Calderwood, David; Wishart, Neil; Arnold, Lee D.; Friedman, Michael M.; US2004/6083; (2004); 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. 113293-71-3, name is (6-Aminopyridin-3-yl)methanol. A new synthetic method of this compound is introduced below., Quality Control of (6-Aminopyridin-3-yl)methanol

General procedure: Triphenylphosphine (TPP) (280 mg, 1.07 mmol) was added in portions to a freshly prepared solution of the designated alcohol (1.0 mmol) and the specified phenolic acid (1.0 mmol equivalent) in anhydrous THF (3.5 mL) at 0 C. Diisopropylazodicarboxylate (DIAD) (208 mL, 1.0 mmol) was then added dropwise to the mixture. The reaction mixture was stirred at 0 C for 30 min. The mixture was then warmed and stirring was continued for 48 h at rt [19]. Reactions were monitored till completion by TLC. The reaction mixture was then worked up by removal of the solvent under reduced pressure, saturated solution of NaHCO3 (10 mL) was added, and then the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate was evaporated under reduced pressure to dryness. The crude product was collected and purified by column chromatography(CC) on Sephadex LH-20 using isocratic CH2Cl2 followed by chromatography on Si gel 60 using n-hexane-EtOAc system, gradient elution, to afford 5-9 and 13-47 (Supplementary Information).

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, 113293-71-3, (6-Aminopyridin-3-yl)methanol.

Reference:
Article; Mohyeldin, Mohamed M.; Busnena, Belnaser A.; Akl, Mohamed R.; Dragoi, Ana Maria; Cardelli, James A.; El Sayed, Khalid A.; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 299 – 315;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 72990-37-5, 3-Chloroisonicotinaldehyde, 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-Chloroisonicotinaldehyde, blongs to pyridine-derivatives compound. Safety of 3-Chloroisonicotinaldehyde

Magnesium (86.5 mg, 3.60 mmol) was stirred vigorously under nitrogen for 30 min. THF (2 mL) and dibromoethane (2 drops) were added and the reaction mixture was warmed to 50 C. A solution of 4-bromotetrahydropyran (495 mg, 3.00 mmol) in THF (4 mL) was added drop-wise over 5 min and the reaction mixture was heated at reflux for 2 h. A solution of 3-chloro-4-pyridaldehyde (170 mg, 1.20 mmol) in THF (4 mL) was added drop-wise over 5 min and the reaction mixture was heated at reflux for 6 h, stirred at room temperature overnight and heated at reflux for 8 h. The reaction mixture was cooled to 0 C and quenched with sat aq NH4C1 (10 mL). The reaction mixture was diluted with EtOAc (40 mL) and the aqueous fraction was extracted with EtOAc (3 x 40 mL). The combined organic fractions were washed with sat aq Na2C03 (20 mL), dried (MgS04) and concentrated in vacuo. The residue was purified by normal phase column chromatography to give the crude title compound as a pale yellow gum (69.0 mg, 25%). LCMS (ES+): 228.2 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72990-37-5, 3-Chloroisonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Proximagen Limited; EVANS, David; CARLEY, Allison; STEWART, Alison; HIGGINBOTTOM, Michael; SAVORY, Edward; SIMPSON, Iain; NILSSON, Marianne; HARALDSSON, Martin; NORDLING, Erik; KOOLMEISTER, Tobias; WO2011/113798; (2011); A2;,
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. 66358-23-4, name is Imidazo[1,2-a]pyridin-5-amine. A new synthetic method of this compound is introduced below., Application In Synthesis of Imidazo[1,2-a]pyridin-5-amine

Example 69: 4-[3-(4-Chloro-phenoxy)-benzyl1-piperazine-1 -carboxylic acid imidazo[1 ,2-aipyridin-5-ylamide.; To a solution of imidazo[1 ,2-a]pyridin-5-ylamine (56.0 mg, 0.421 mmol) in CH2CI2 (2.0 ml_) were added N,N’-disuccinimidyl carbonate (108 mg, 0.421 mmol) and DMAP (51.0 mg, 0.417 mmol). The reaction mixture was stirred at rt for 6 h, then treated with 1-[3-(4-chloro-phenoxy)-benzyl]-piperazine hydrochloride (158 mg, 0.420 mmol) and diisopropylethylamine (109 mg, 0.840 mmol) and stirred for an additional 16 h at rt. The reaction mixture was diluted with EtOAc and extracted with H2O then saturated aqueous NaCI. The organic layer was dried (MgSO4), and concentrated. The crude residue was purified (FCC, 2 N NH3 in MeOH/DCM) to give 4-[3-(4-chloro- phenoxy)-benzyl]-piperazine-1 -carboxylic acid imidazo[1 ,2-a]pyridin-5-ylamide (90.0 mg, 46%). MS (ESI+): calcd for C25H24CIN5O2 m/z 461.17, found 462.2 (M+H)+. 1H NMR (d6-DMSO): 9.21 (br s, 1 H), 7.57 (s, 1 H), 7.54 (d, J = 1.2, 1 H), 7.47-7.35 (m, 4H), 7.23 (dd, J = 9.0, 7.2, 1 H), 7.15 (d, J = 7.6, 1 H), 7.06-7.01 (m, 3H), 6.94 (dd, J = 8.1 , 1.9, 1 H), 6.73 (d, J = 7.1 , 1 H), 3.54 (s, 2H), 3.52-3.45 (m, 4H), 2.46-2.40 (m, 4H).

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, 66358-23-4, Imidazo[1,2-a]pyridin-5-amine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BREITENBUCHER, J., Guy; KEITH, John, M.; TICHENOR, Mark, S.; CHAMBERS, Alison, L.; JONES, William, M.; HAWRYLUK, Natalie, A.; TIMMONS, Amy, K.; MERIT, Jeffrey, E.; SEIERSTAD, Mark, J.; WO2010/68453; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem