Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 733757-89-6, tert-Butyl 3-(trifluoromethyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate, 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, 733757-89-6, blongs to pyridine-derivatives compound. Application In Synthesis of tert-Butyl 3-(trifluoromethyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate

Description 21 : 6-methyl-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4- c] pyridineUnder an inert atmosphere of argon, LiAIH4 (2.3 M in THF; 7.5ml; 17.3mmol) was added dropwise over 2 minutes to a cool (O0C) stirring solution of 6-tert-butoxycarbonyl-3- (trifluoromethyl)-4,5,6,7-tetrahydro-1 H-pyrazolo[3,4-c]pyridine (2.0Og; 8.45mmol) in anhydrous THF (42ml). The resulting mixture was stirred in an oil bath at 580C for 17 hours, cooled to O0C, and quenched by the careful addition of an aqueous solution of sodium potassium tartrate (1 M; 50ml). After stirring at room temperature for 1 hour, the mixture was diluted with diethyl ether (50ml) and more aqueous sodium potassium tartrate (1 M; 50ml). After stirring at this temperature for a further 1 hour, the mixture was partitioned between water (100ml) and diethyl ether (200ml). The separated aqueous phase was extracted with ethyl acetate (200ml), and the combined organic phase was dried (MgSO4) and concentrated in vacuo. The resulting off-white solid (1.39g) was purified using an SCX column giving the title compound as a yellow solid (1.23g; 6.01 mmol)LC/MS (ES): Found 206 (ES+), retention time 1.81 mins. C8H10F3N3 requires 205.1 H-NMR (400MHz, CDCI3): 2.48 (3H, app s), 2.74 (4H, app s), 3.58 (2H, app s), 5.01(1 H, br s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,733757-89-6, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/113795; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 230301-11-8, tert-Butyl 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate, 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: tert-Butyl 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate, blongs to pyridine-derivatives compound. Recommanded Product: tert-Butyl 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate

To a stirred solution of tert-butyl 1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-5-carboxylate(1 g, 4.479 mmol, 1 equiv.) in MeCN(120 mL) was added NIS(1.11 g, 4.927 mmol, 1.1 equiv.) at room temperature. The resulting mixture was stirred for 4 h at 60 degrees C. The reaction was monitored by LCMS. The resulting mixture was concentrated under reduced pressure. The residue was purified by reverse phase flash with the following conditions (Column: C18, 330 g; Mobile Phase A: Water/0.05% TFA, Mobile Phase B: ACN; Flow rate: 80 mL/min; Gradient: 35%B to 55%B in 25 min; Detector, 220nm; Monitor,254 nm) to afford tert-butyl 3-iodo- 1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-5-carboxylate(390 mg, 24.94%) as a dark yellow solid

The synthetic route of 230301-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
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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.40296-46-6, name is Ethyl 4,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, molecular weight is 220.0527, as common compound, the synthetic route is as follows.Product Details of 40296-46-6

Example IX Preparation of [(4,6-dichloropyridin-3-yl)methyl](methyl)-oxido lambda4-sulfanylidenecyanamide (9) To a stirred solution of ethyl 4,6-dichloronicotinate (8.8 g, 40 mmol) in anhydrous THF (75 mL) cooled in an ice-water bath was added in a dropwise fashion 1 M LiAlH4 solution in THF (25 mL, 25 mmol). During the addition, the temperature was not allowed to rise above 25 C. After the addition was over, the reaction was warmed to 40 C. for 15 min, cooled, then quenched by the successive dropwise addition of water (0.95 mL), 15% aqueous NaOH (0.95 mL) and water (1.85 mL). The mixture was filtered through celite and the filtrated was dried (MgSO4), passed through a short pad of silica gel and concentrated to give a red oil. Ether (100 mL) was added whereupon a gummy precipitate immediately appeared, which was removed by filtration. The ether solution was allowed to stand at room temperature overnight, during which time more precipitate was formed which was removed again by filtration. The ether solution was concentrated and dried to give 3.25 g of the product 2,4-dichloro-5-hydroxy-methylpyridine in 46% yield as a nearly colorless oily solid. 1H NMR (300 MHz, CDCl3) delta 8.5 (s, 1H), 7.4 (s, 1H), 4.8 (s, 2H), 2.7 (bs, 1H); GC-MS: mass calcd for C6H5Cl2NO [M]+, 177. Found

At the same time, in my other blogs, there are other synthetic methods of this type of compound,40296-46-6, Ethyl 4,6-dichloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Zhu, Yuanming; Loso, Michael R.; Nugent, Benjamin M.; Huang, Jim X.; Rogers, Richard B.; US2008/108667; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89856-44-0, 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 89856-44-0, name is 5-Bromo-4,6-dimethylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Preparation Example 38 Synthesis of 3-bromo-6-fluoro-2,4-dimethylpyridine 2-amino-5-bromo-4,6-dimethylpyridine (2 g) was suspended in fluoroboric acid (48% aqueous solution, 7.5 mL). Sodium nitrite (890 mg) dissolved in water (3 mL) was added to the solution at 0 C. The reaction mixture was stirred at 0 C. for 10 minutes. The precipitated solid was collected by filtration and suspended in n-heptane (100 mL). The solution was stirred with heating under reflux for two hours. After cooling to room temperature, the precipitated solid was collected by filtration. The resulting solid was dried under reduced pressure to give the title compound (500 mg). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.43 (s, 3H), 2.62 (s, 3H), 6.67 (s, 1H).

According to the analysis of related databases, 89856-44-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki; US2013/143907; (2013); A1;,
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Pyridine | C5H5N – PubChem

Related Products of 130722-95-1, Adding some certain compound to certain chemical reactions, such as: 130722-95-1, name is 3-(Benzyloxy)-5-bromopyridine,molecular formula is C12H10BrNO, 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 130722-95-1.

3-Benzyloxy-5-bromopyridine (15.0 g, 56.8 mmol), prepared as described in (US 5,733,912), and 30% HBr/acetic acid (200 mL) were stirred at ambient temperature for 16 hours. The reaction was diluted with diethyl ether (500 mL) and the resulting white solid (12.9 g) was isolated by filtration. The solid was taken up in methanol (300 mL) and concentrated NH4OH (50 mL) was added. After stirring at ambient temperature for 12 hours, the mixture was concentrated under reduced pressure to provide the title compound as a white solid (9.8 g, 89%). MS (DCI/NH3) m/z 174/176 (M+H)+.

According to the analysis of related databases, 130722-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; EP1428824; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 98273-19-9, 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.98273-19-9, name is Methyl 4,6-dichloropicolinate, molecular formula is C7H5Cl2NO2, molecular weight is 206.03, as common compound, the synthetic route is as follows.

Methyl 4-chloro-6- and methyl 6-chloro-4-morpholinopicolinateA screw-cap vial was charged with methyl 4,6-dichloropicolinate (0.300 g, 1.456 mmol), potassium carbonate (0.302 g, 2.184 mmol), palladium (II) acetate (0.016 g, 0.073 mmol), XPhos (0.104 g, 0.22 mmol), morpholine (0.127 mL, 1.46 mmol), and toluene (5 mL). The yellow solution was stirred at 100 C for 18 h, then filtered through Celite and concentrated. The crude material was purified by column chromatography (silica, 0-50% ethyl acetate in hexanes) to afford (in order of elution) methyl 4-chloro-6-morpholinopicolinate and methyl 6-chloro-4- morpholinopicolinate as white amorphous solids. Isomers assigned by NOESY. Mass Spectrum (ESI) m/e = 257.0 (M + 1); 257.0 (M + 1).

Statistics shows that 98273-19-9 is playing an increasingly important role. we look forward to future research findings about Methyl 4,6-dichloropicolinate.

Reference:
Patent; AMGEN INC.; DRANSFIELD, Paul John; GONZALEZ LOPEZ DE TURISO, Felix; PATTAROPONG, Vatee; SIMARD, Jillian L.; WO2012/3264; (2012); 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. 52718-95-3, name is Methyl 2-bromonicotinate. A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-bromonicotinate

Step 1) Methyl 2-[(4-Hydroxymethyl)phenyl]-3-pyridinecarboxylate To a stirred solution of methyl 2-bromo-3-pyridinecarboxylate (3.45 g, 14.39 mmol) and 4-(trimethylstannyl)benzyl alcohol (3.90 g, 14.39 mmol), prepared as described in Step 1 of Example 3, in DMF (25 mL) was added bis(acetonitrile)palladium dichloride (0.19 g, 0.72 mmol) and CuI (0.27 g, 1.44 mmol). After 18 h, bis(triphenylphosphine)palladium dichloride (0.20 g, 0.28 mmol) and CuI (0.11 g, 0.57 mmol) were added and stirring was continued for 2 days at room temperature. The mixture was concentrated, taken up in water, and extracted with EtOAc. The combined extracts were washed with brine, dried, and concentrated. Purification by flash chromatography (50% EtOAc/hexane) gave 277 mg (8%) of product as a yellow oil. 1 H NMR (CDCl3) delta 3.69 (s, 3H), 4.69 (s, 2H), 7.35 (m, 1H), 7.38 (d, J=8.2 Hz, 2H), 7.49 (d, J=8.2 Hz, 2H), 8.08 (dd, J=7.9, 1.8 Hz, 1H), 8.75 (m, 1H).

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, 52718-95-3, Methyl 2-bromonicotinate.

Reference:
Patent; American Home Products Corporation; US5283242; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1214334-70-9 ,Some common heterocyclic compound, 1214334-70-9, molecular formula is C7H6BrNO3, 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.

5-bromo-6-methoxy-N,N-dimethylpicolinamide (0305) To a solution of 5-bromo-6-methoxypyridine-2-carboxylic acid (1.0 g, 4.31 mmol) in DMF (10 mL) were added dimethylamine (1.5 g, 33.27 mmol), HATU (2.0 g, 5.13 mmol) and DIEA (1.7 g, 12.77 mmol) at room temperature. The resulting solution was stirred for 2 h at 100 C. The reaction mixture was cooled to room temperature and treated with water (50 mL). The resulting mixture was extracted with ethyl acetate (100 mL×3). The organic phases were combined, washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to yield 5-bromo-6-methoxy-N,N-dimethylpyridine-2-carboxamide as black oil (1.2 g, crude). MS: m/z=259.0 [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,1214334-70-9, its application will become more common.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 524955-09-7, 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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. A new synthetic method of this compound is introduced below.

Following hydrogenation to form the first aniline intermediate, acid catalyzed coupling was performed to prepare 4-[3-chloro-4-(2-pyridylmethoxy)anilino]-3-cyano-7-ethoxy-6-N-acetylaminoquinoline, as shown below: To perform the coupling reaction, the two reactants were heated together in alcohol at 65-78 C. over 4-6 hours, yielding the product. The reaction begins as an amber slurry and thickens to a lighter beige slurry as it approaches completion. Upon scaling up from 75 g to 350 g, it proved necessary to add a catalytic amount (0.025 eq.) of methanesulfonic acid to initiate the reaction. As a specific example, 4-chloro-3-cyano-7-ethoxy-6-N-acetylaminoquinoline (0.141 kg, 0.49 mole) was added to the mixture of Example 2, followed by ethanol (0.037 L) to give a suspension. A catalytic amount of methanesulfonic acid (1.17 g) was added at 20-25 C. The resulting slurry was heated to 70-75 C. and held for a minimum of 4 hours. Thickening of the slurry was evident after 1.5 hours. Following reaction completion, the mixture was cooled to room temperature and may be used ?as is? in the telescoped reaction of Example 4 below.; As solvents EtOH, DMF or other suitable solvent may be used. Experimental results obtained using different solvents and reaction conditions are shown in Table 3. Difficulty filtering the product of this step (noted in several entries on Table 3) was circumvented by not isolating the solid at this point, but telescoping the reaction with the next step. It has been found that on the order of 20 volumes of EtOH were necessary to achieve reasonable stirring, but that the reaction can proceed in only 10 volumes of DMF, without significant loss in purity. In Table 3, where the entry is labelled NI, the intermediate product was not isolated, but carried into the next reaction step. TABLE 3 Coupling Reaction Coupling Temp Time Yield Solvent Solvent ( C.) (h) (%) Comments IPA EtOH 78 4 85.4 contains impurity THF EtOH 78 4 90.5 v. slow filtration THF THF 68 4 NA Only 16% product formed THF EtOH 78 4 94.2 v. slow filtration EtOH IPA 82 5 NA No reaction EtOH MeOH 65 5 60.0 v. slow filtration THF EtOH 78 1.5 80.3 v. slow filtration (MeSO3H) THF EtOH 78 4 86.0 v. slow filtration THF EtOH 78 3 85.7 4 h filtration – hard, green (MeSO3H) coated solid on drying THF Dimethoxy 85 2 74.2 Faster filtration (<1 hr) ethane Nice yellow solid THF Diethoxy 85 5 - - Methane THF Dimethoxy 70 6 - - Ethane THF EtOH 78 6 96.6 Slow filtration THF DMF 78 0.5 65.6 Some product lost in filtrate (MeSO3H) THF DMF 70 8 NI See Note 1 (MeSO3H) THF EtOH 78 6 ND See Note 2 (MeSO3H) THF EtOH 78 4 NI Yield to the free base is (MeSO3H) 80.4%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 83%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 86%3/ NR = no reaction, NI = not isolated; ND = not determined; NA = not available 1. Carried through to the deprotection and generation of free base to give 69.5% overall yield. 2. The overall yield after the deprotection and generation of the free base is 76.1% 3This reaction was not filtered at all but taken as slurry to the next step. At the same time, in my other blogs, there are other synthetic methods of this type of compound,524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, and friends who are interested can also refer to it. Reference:
Patent; WYETH; US2006/270668; (2006); 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. 152460-10-1, name is N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine. This compound has unique chemical properties. The synthetic route is as follows. Safety of N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine

General procedure: The final target compounds were synthesized from 6-methyl-N-(4-(pyridin-3-yl) pyrimidin-2-yl) benzene-1,3-diamine 8(2 mmol), DMF (10 mL), and DIPEA (4 mmol) followed by substituted aromatic acid (2 mmol) was added and stirred at room temperature for 1 h. After completion of the reaction mixture was poured into ice-cold water. The obtained yellow precipitate washed with water and dried to get target titled product pyrimidine scaffold benzamide derivatives (9 a-k).

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, 152460-10-1, N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine.

Reference:
Article; Thirumurugan; Lakshmanan, Sivalingam; Govindaraj, Dharman; Daniel Prabu, D. Sam; Ramalakshmi; Arul Antony; Journal of Molecular Structure; vol. 1171; (2018); p. 541 – 550;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem