Category: 53014-84-9

Reference of 53014-84-9, 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.53014-84-9, name is 2-Methyl-5-formylpyridine, molecular formula is C7H7NO, molecular weight is 121.1366, as common compound, the synthetic route is as follows.

154. (+)-2- 3,4-trans)-4-methyl-l-g6-methylpyridin-3- yl)methyl)pyrrolidin-3-yl)-7-ftetrahvdro-2H-pyran-4-yl)imidazo[5,l- f] ri,2,41triazin-4(3H)-one [1113] To a stirred solution of (-)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7- (tetrahydro-2H-pyran-4-yl)imidazo[5,l- J[l,2,4]triazin-4(3H)-one (150 mg, 0.49 mmol) in MeOH (10 mL) was added 6-methylnicotinaldehyde (71 mg, 0.59 mmol) at room temperature and stirred for 2 h under argon atmosphere. To the resulting solution was added NaCNBH3 (93 mg, 1.48 mmol) and stirring was continued for another 8 h at room temperature. The volatiles were evaporated under reduced pressure. The residue was diluted with water and extracted with CH2CI2 (2 x 20 mL). Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford (+)-2-((3,4-trans)-4-methyl-l-((6-methylpyridin-3- yl)methyl)pyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4-yl)imidazo[5, 1 -f [ 1 ,2,4]triazin- 4(3H)-one (43 mg, 21%) as an off-white solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.38 (s, 1H), 7.67 (s, 1H), 7.58 (d, 1H), 7.21 (d, 1H), 3.97-3.91 (m, 2H), 3.64-3.59 (m, 2H), 3.52-3.49 (m, 1H), 2.94-2.92 (m, 1H), 2.87-2.84 (m, 2H), 2.79-2.71 (m, 2H), 2.67-2.61 (m, 2H), 2.42 (s, 3H), 2.24-2.21 (m, 1H), 1.87-1.82 (m, 4H), 1.09 (d, 3H); Mass (ESI): 409.3 [M++l]; LC-MS: 96.82%; 409.4 (M++l); (column; Eclipse XDB C-18, (150×4.6 mm, 5.0mu); RT 5.58 min. 0.05% TFA (Aq): ACN; 1.0 ml/min); UPLC (purity): 98.45%; (column; Acquity UPLC HSS-T3, 100×2.1 mm, 1.8mu; RT 2.83 min. 0.025% TFA (Aq): ACN; 0.30 ml/min; Chiral HPLC: 99.61%, R,= 9.69 min (Chiralpak IA, 250 x 4.6mm, 5mu; mobile phase (A) 0.1% DEA in n-Hexane (B) DCM:MeOH (80:20) (A: B : 80:20); flow Rate: 1.00 mL/min); Optical rotation [a]D20: + 18.96 (c = 0.25, DCM). TLC: 5% MeOH/DCM (Rf: 0.3).

The chemical industry reduces the impact on the environment during synthesis 53014-84-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53014-84-9, 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.53014-84-9, name is 2-Methyl-5-formylpyridine, molecular formula is C7H7NO, molecular weight is 121.1366, as common compound, the synthetic route is as follows.

INTERMEDIATE 552- [(Hydroxy)(6-methylpyridin-3-yl)methyll acrylic acid ethyl esterTo a solution of 6-methylpyridine-3-carbaldehyde (5.0 g, 41 mmol) in ethyl acrylate (10 mL) at room temperature was added DABCO (1.0 g, 9 mmol), and the mixture was stirred overnight. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography (Si02, hexane to 40%> ethyl acetate), to give the title compound (5.6 g, 62%) as a yellow oil. LCMS (ES+) 222.2 (M+H)+, RT 0.98 minutes.

The chemical industry reduces the impact on the environment during synthesis 53014-84-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; UCB PHARMA S.A.; PARTON, Andrew Harry; ALI, Mezher Hussein; BROOKINGS, Daniel Christopher; BROWN, Julien Alistair; FORD, Daniel James; FRANKLIN, Richard Jeremy; LANGHAM, Barry John; NEUSS, Judi Charlotte; QUINCEY, Joanna Rachel; WO2012/32334; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 53014-84-9 ,Some common heterocyclic compound, 53014-84-9, molecular formula is C7H7NO, 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.

A. Alpha-amino-alpha-(6-methyl-3-pyridinyl)acetonitrile To a solution of potassium cyanide (6.96 g, 107 mmol) and ammonium chloride (5.72 g, 107 mmol) in water (5 ml) was added 6-methyl-3-pyridin-carboxaldehyde (8.68 g, 71.5 mmol) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was basified with 50% NaOH and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated to give the crude desired product in 7 g yield. The product was used without further purification.

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. 53014-84-9, 2-Methyl-5-formylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Novo Nordisk A/S; US5328923; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 53014-84-9, 2-Methyl-5-formylpyridine, 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: GeneralReductive Amination Procedure: A 2-dram round-bottomed vial was charged withthe crude amine/TFA salt prepared using the general displacement procedure followed by the general TFA de-protection procedure (0.115 mmol), DCE(2 mL), DIPEA (6 eq. 0.690 mmol), DMF (1 mL), the aldehyde (1 equiv., 0.115mmol), and the reaction mixture was shaken for 1 h at RT. The reaction mixture was then treated with NaBH(OAc)3(2.5 equiv., 0.230 mmol) and the reaction was shaken 16 h at RT. Ther eaction mixture was then diluted with DCE (2 mL) and NaHCO3 (2mL). The aqueous layer was back extracted with DCE (2 x 2 mL) and the combined organic layer was concentrated under reduced pressure (Genevac HT-4) and the crude residue was purified usin greverse phase HPLC (MS-triggered fraction collection) with an acetonitrile/water or methanol/water gradient and trifluoroacetic acid as the modifier. The pure fractions were then concentrated under reduced pressure (Genevac HT-4) to afford the pure productsas the TFA salt. General De-Protection Procedure:The crude protected products were prepared using the General Displacement Procedure and were then treated with 2 mL DCE and 500muL of TFA and shaken for24 h. The solvent was removed underreduced pressure (Genevac HT-4) and the crude residues were purified using reverse phase HPLC (MS-triggered fraction collection) with an acetonitrile/water or methanol/water gradient and trifluoroacetic acid as a modifier. The pure fractions were then concentrated under reduced pressure (Genevac HT-4).(Z)-5-((2-(4-((((6-methylpyridin-3-yl)methyl)amino)methyl)piperidin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione(21) was prepared using the general reductive amination procedure and the general de-protection procedure with compound 13 and 6-methylnicotinaldehyde (15.5 mg, 41.7 mg theoretical,37.2%). LC-MS m/z 397.5 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53014-84-9, 2-Methyl-5-formylpyridine, and friends who are interested can also refer to it.

Reference:
Article; Flanders, Yvonne; Dumas, Stephane; Caserta, Justin; Nicewonger, Robb; Baldino, Michael; Lee, Chee-Seng; Baldino, Carmen M.; Tetrahedron Letters; vol. 56; 23; (2015); p. 3186 – 3190;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 53014-84-9, 2-Methyl-5-formylpyridine, 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, Application In Synthesis of 2-Methyl-5-formylpyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Methyl-5-formylpyridine

C. Preparation of 6-methylnicotinaldehyde oxime To a solution of 6-methylnicotinaldehyde (1.67 g, 13.79 mmol) in 27.6 mL MeOH, hydroxylamine (50% weight in water, 0.87 mL, 14.2 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and then at 40 C. for an additional 2 h. The reaction mixture was concentrated to obtain 1.76 g (94%) of the title compound as a light brown solid. HPLC: retention time=0.20 min.

The synthetic route of 53014-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun, Chongqing; Sher, Philip M.; Wu, Gang; Ewing, William R.; Huang, Yanting; Lee, Taekyu; Murugesan, Natesan; Sulsky, Richard B.; US2007/4772; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53014-84-9 , The common heterocyclic compound, 53014-84-9, name is 2-Methyl-5-formylpyridine, molecular formula is C7H7NO, 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.

Example 15 Preparation of 2-methyl-5-(oxiran-2-yl)py?dme [0380] The title compound was prepared by following general procedure 3 DMSO (4mL) was added to NaH 60% dispersion in oil (0 314 g, 7 8 mmol, 1 3 equiv ) and heated to 65 0C for 1 h THF (1OmL) was added at the same temperature and heated for another 10 mm After 10 mm , the reaction mixture was cooled to 00C T?methylsulfomum iodide (1 2 g, 5 9 mmol, 1 equiv ) was added and stirred for 10 mm and then a solution of 6-methylmcotmaldehyde (0 720 g, 5 9 mmol, 1 equiv ) in THF was added dropwise After complete addition, the reaction mixture was stirred at RT for 2 h, the product was detected by LCMS The reaction mixture was poured into ice water and the product was extracted in diethyl ether (4 x 5OmL), dried over Na2SO4 and concentrated at 25 0C to get the crude product 2-methyl-5-(oxiran-2-yl)py?dme (1 1 g crude)

The synthetic route of 53014-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; HUNG, David, T.; PROTTER, Andrew, Asher; JAIN, Rajendra, Parasmal; CHAKRAVARTY, Sarvajit; GIORGETTI, Marco; WO2010/51503; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 53014-84-9, 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. 53014-84-9, name is 2-Methyl-5-formylpyridine. A new synthetic method of this compound is introduced below.

Ethyl cyanoacetate (607 mg, 5,36 mmol), 6-methylpyridine-3~carbaldehyde (650 mg, 5.36 mmol), piperidine (0.26 mL) and acetic acid (48 mg) were siiiTed in eihanol (10 mL) at RT for 16 h. The mixture was diluted in TBME/Heptane and cooled on dry ice to induce precipitation. Solid formed was filtered off and washed with peniane to give the title compound as a white solid (0.89 g, 70%), 1H NMR (500 MHz, Chlorofonn-d) delta 8.78 (d, J – 2.3 Hz, 1H) 8.51 (dd, J – 8.3, 2.4 Hz, 1H), 8.23 (s, 1H), 7.32 (d, J = 8.3 Hz, 1 H), 4.40 (q, J = 7.1 Hz, 2H), 2.65 (s, 3H), 1.40(t, J – 7, 1 Hz, 3H). LCMS Method C: rt 1.08 min; 91 % m/z 216.9 (MH?),

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53014-84-9, 2-Methyl-5-formylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; EVOTEC INTERNATIONAL GMBH; GAMPE, Christian, M.; KAHNE, Daniel, Evan; KAHNE, Suzanne, Walker; QIAO, Yuan; EAST, Stephen; PARKES, Alastair, L.; SOUTHEY, Michelle; HUNTER, James; WHITTAKER, Mark; ARTHUIS, Martin; (359 pag.)WO2016/191658; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53014-84-9, 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 53014-84-9, name is 2-Methyl-5-formylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution containing the product from Example 6F (0.150 g, 0.65 mmol) in a mixture of toluene (2.5 mL) and methanol (2.5 mL) was treated with the product from Example 13A (0.079 mL, 0.65 mmol), stirred at 50 C. for 16 hours, cooled to 25 C., treated with sodium borohydride (0.049 g, 1.29 mmol), stirred at 25 C. for 1 hour, quenched with 1N NaHCO3 and stirred for 1 hour, and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. A solution of the concentrate (0.194 g) in 1,2-dichloroethane (10 mL) was treated with N,N-disuccinimidyl carbonate (0.20 g, 0.781 mmol) and triethylamine (0.11 mL, 0.789 mmol), stirred at 25 C. for 16 hours, and partitioned with 10% Na2CO3. The aqueous was extracted with additional chloroform. The combined organic phase was dried over MgSO4, filtered and concentrated. A solution of the concentrate (0.223 g) in dichloromethane (2.5 mL) was treated with trifluoracetic acid (2.5 mL), and the mixture was stirred at 25 C. for 2 hours. The solvent was concentrated to give the title compound (0.379 g) as the trifluoroacetic acid salt, which was used without further purification.

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 53014-84-9, 2-Methyl-5-formylpyridine.

Reference:
Patent; DeGoey, David A.; Flentge, Charles A.; Flosi, William J.; Grampovnik, David J.; Kempf, Dale J.; Klein, Larry L.; US2005/131017; (2005); 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. 53014-84-9, name is 2-Methyl-5-formylpyridine. A new synthetic method of this compound is introduced below., Safety of 2-Methyl-5-formylpyridine

EXAMPLE 3 2-[[4-(3-Methoxy-2-pyridyl)butyl]amino]-5-[(6-methyl-3-pyridyl)hydroxymethyl]-4-(1H)-pyrimidinone 2-[[4-(3-Methoxy-2-pyridyl)butyl]amino]-4-(1H)-pyrimidinone (1.42 g, 0.005 mol) was dissolved in concentrated hydrochloric acid (10 ml) and 2-methyl-5-formylpyridine (1.35 g, 0.012 mol) was added. The solution was stirred at reflux temperature for 24 hours, cooled, basified with 10N sodium hydroxide to pH 8.5 and the product left to separate as an oil. The aqueous mother liquor was decanted and the oil subjected to medium pressure liquid chromatography (Kieselgel 60, 230-400 mesh) with methanolic ammonia: dichloromethane (10:90) as eluent. The relevant fractions were combined and evaporated under reduced pressure to afford the title compound (0.63 g). Crystallisation from aqueous methanol afforded the title product as a white crystalline solid, m.p. 82 C.; delta(CDCl3) 1.6 (4H, m), 2.5 (3H, s) 2.75 (2H, m), 3.3 (2H, m), 3.8 (3H, s), 5.7 (1H, s), 7.1 (3H, m), 7.4 (1H, s), 7.65 (1H dd), 7.9 (1H, dd), 8.5 (1H, m) ppm.

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, 53014-84-9, 2-Methyl-5-formylpyridine.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4569996; (1986); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem