Category: 25016-11-9

25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C5H6N2O

EXAMPLE 51 (Z)-2-(5-methoxy-1H-indol-3-yl)-3-(1-methyl-1H-pyrazol-3-yl)-acrylonitrile To a solution of sodium methanolate (204 mg, 3.8 mmol, 1.4 eq.) in anhydrous ethanol (30 mL) were added, under an argon atmosphere, (5-methoxy-1H-indol-3-yl)-acetonitrile (500 mg, 2.7 mmol, 1.0 eq.) and, after 30 minutes stirring, 1-methyl-1H-pyrazole-4-carbaldehyde (326 mg, 3.0 mmol, 1.1 eq.). The reaction apparatus was protected from light and the mixture heated at 50 C. for 18 hours. The reaction was allowed to cool to room temperature and then, the solvent was removed under reduced pressure and the crude taken up in ethyl acetate. The organic layer was washed with water and brine, dried over MgSO4 and then, evaporated. The residue was purified by silica gel flash-column chromatography (eluent: CH2Cl2/EtOH, 99/1 to 98/2) to afford, after trituration with diethyl ether, the compound (51) as a beige powder (640 mg, 85%). mp: 178 C.; 1H NMR (DMSO, 300 MHz) delta (ppm): 3.81 (3H, s, 5′-methoxy), 3.92 (3H, s, N-methyl), 6.90 (1H, dd, J6′-7’=8.7 Hz, J6′-4’=2.3 Hz, H6′), 7.37 (1H, d, J7′-6’=8.7 Hz, H7′), 7.38 (1H, m, H4′), 7.55 (1H, s, H3), 7.61 (1H, s, H2′), 8.00 (1H, s, H3″), 8.24 (1H, s, H5″), 11.43 (1H, s, indolic H); 13C NMR (DMSO, 75.5 MHz) delta (ppm): 38.8 (N-methyl), 55.6 (5′-methoxy), 101.5 (C2), 101.5 (C4′), 109.8 (C3′), 111.9 (C6′), 112.9 (C7′), 117.4 (C4″), 119.3 (C1), 124.0 (C3a’), 125.6 (C2′), 128.5 (C3), 131.0 (C5″), 132.1 (C7a’), 138.8 (C3″), 154.1 (C5′); MS: ESI-MS: m/z 264.1 ([M+H]+), 286.1 ([M+Na]+); HRESI-MS: m/z 301.1060 (calcd for C16H14N4ONa+, 301.1065); Anal. Calcd for C19H14N4O, 0.1H2O: C, 68.61; H, 5.11; N, 20.00; O, 6.55. Found: C, 68.73; H, 5.33; N, 19.69.

The synthetic route of 25016-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COMMISSARIAT A L’ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; Guillou, Catherine; Kozielski, Frank; Labriere, Christophe; Gueritte, Francoise; Tcherniuk, Sergey; Skoufias, Dimitrios; Thal, Claude; Husson, Henri-Philippe; US9212138; (2015); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 25016-11-9, 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. 25016-11-9 name is 1-Methyl-1H-pyrazole-4-carbaldehyde, This 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.

Acetic acid (101muL; 1.76mmol) was added under nitrogen atmosphere, at rt to a solution of intermediate 27 (430mg; 0.88mmol) and 1-methyl-1H-pyrazole-4- carbaldehyde( CAS [25016-11-9]) (194mg; 1.76mmol) in THF (15mL). The mixture was stirred at rt for 3 hours. Subsequently, NaBH(OAc)3 (561mg; 2.65mmol) was added portionwise and the mixture was stirred at rt for 15 hours. The mixture was poured into a mixture of water, and a 10% solution of K2CO3. EtOAc was added and stirred at rt for 15 min and extracted with EtOAc (x2). The organic layers were combined, dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (Stationary phase: irregular SiOH 15-40mum 24g GRACE, Mobile phase: Gradient from 0.1% NH4OH, 97% DCM, 3% MeOH to 0.1% NH4OH, 95% DCM, 5% MeOH). The fractions containing product were collected and evaporated to dryness yielding 420 mg (82%) of intermediate 28.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-pyrazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PATRICK, Aaron, Nathaniel; PILATTE, Isabelle, Noelle, Constance; (157 pag.)WO2018/109088; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C5H6N2O, 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. Application In Synthesis of 1-Methyl-1H-pyrazole-4-carbaldehyde

General procedure: Benzaldehyde (30muL, 0.30mmol) was added to a mixture of 14 (100mg, 0.24mmol) and acetic acid (4.1muL, 0.07mmol) in CH2Cl2 (2.5mL). The mixture was stirred at room temperature for 0.5h. Sodium trisacetoxyborohydride (101mg, 0.48mmol) was added and the mixture was stirred at room temperature overnight. The mixture was neutralized with sat. NaHCO3(aq) and extracted with CHCl3. The organic layer was washed with brine, dried over Na2SO4, and concentrated at reduced pressure. The residue was purified by silica gel column chromatography (CHCl3/MeOH) to give the desired compound as a colorless solid (82.7mg, 68%).Compound 15i was prepared by a procedure similar to that described for 15h to give a colorless solid (yield 61%). 1H-NMR (DMSO-d6) delta 1.84-1.94 (1H, m), 2.37-2.48 (2H, m), 2.73-2.82 (2H, m), 2.88-2.94 (1H, m), 3.08 (3H, s), 3.49 (2H, s), 3.76-3.78 (3H, m), 4.01 (3H, s), 4.04 (3H, s), 5.36-5.42 (1H, m), 7.14 (1H, s), 7.31-7.33 (1H, m), 7.58 (1H, s), 8.07 (1H, s), 8.42 (1H, d, J?=?2.2?Hz), 8.82 (1H, d, J?=?2.2?Hz), 9.37 (1H, br). ESI-MS m/z 513.4 [(M?+?H)+]. HRMS(ESI) m/z calcd for C23H29N8O4S [(M?+?H)+]: 513.2027, found: 513.2027.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25016-11-9, its application will become more common.

Reference of 25016-11-9, A common heterocyclic compound, 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C5H6N2O, 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 mixture of the combined organic layer having 1-methyl-1H-pyrazole-4-carbaldehyde and ethyl acetate obtained from step 1, hydroxylamine hydrochloride (63.48 gm, 0.9135 moles) were refluxed at 70-80 C. for 2-4 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 0-5 C., to this added DM water (100 ml) and 25% aqueous ammonia solution (100 ml) at 0-5 C. The reaction mixture was stirred for 10 min at 20-30 C. The organic layer was separated and aqueous layer was extracted with ethyl acetate (250 ml). The entire organic layer was transferred to the reaction vessel and washed with 10% brine solution (500 ml). Stirred for 10 min and separated the final aqueous layer and organic layer. The organic layer was evaporated to obtain the 1-methyl-1H-pyrazole-4-carbaldehyde oxime.

The synthetic route of 25016-11-9 has been constantly updated, and we look forward to future research findings.

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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Methyl-1H-pyrazole-4-carbaldehyde

Step 2) Potassium ?-butoxide (23.47 g, 199.1 mmol, 2.44 eq.) was suspended in anhydrous DME (90 mL) and cooled to – 60C. Tosyl methyl isocyanide (23.76 g, 121.7 mmol, 1.49 eq.) was dissolved in anhydrous DME (75 mL) and the solution was added drop-wise to the potassium ?-butoxide solution over 20 minutes. After stirring for 20 minutes between – 60 and – 55C, the aldehyde from Step 1 in anhydrous DME (55 mL) was added over 23 minutes. The reaction was stirred for one hour at – 55 to – 50C, and then methanol (90 mL) was added. The cooling bath was removed, and after stirring for 5 minutes in air, the reaction flask was immersed in an oil bath preheated to 85C. The reaction was stirred for 1 hour. After cooling, the mixture was concentrated and the resulting tan solid was dissolved in water (180 mL) with acetic acid (9 mL). This was extracted with ethyl acetate (3 x 250 mL), and these extracts were combined, washed with brine (100 mL), dried over sodium sulfate, filtered and concentrated to yield a brown oil (13.71 g). This oil was dissolved in dichloromethane and purified by silica-gel chromatography using a gradient from 0% to 15% dichloromethane-acetone to yield a bright yellow oil in 63% yield (7.89 g).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Application of 25016-11-9, The chemical industry reduces the impact on the environment during synthesis 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

General procedure: To the solution of 45.0 g aldehyde 10 (0.363 mol) in 225 cm3 pyridine, 45.4 g malonic acid (0.436 mol) and 0.900 g piperidine (10.9 mmol) were added. The resulting mixture was heated at 70 C for 3 days. The solvent was removed in vacuo, and the residue was triturated with H2O. The precipitate was filtered to give the product 11

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, 1-Methyl-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

These common heterocyclic compound, 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, 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. Quality Control of 1-Methyl-1H-pyrazole-4-carbaldehyde

General procedure: A mixture of appropriate aldehyde (10 mmol) from the list a-t, compound 4 (10 mmol), ZnO Nano particles (2 mmol) and ethanol (25 mL) was stirred at rt for 30 min to 1 h. After completion of reaction (monitored by TLC), the reaction mixture was filtered through a nanofiltration membrane (Make: Synder, Model: NFS 100-250Da). The filtrate was evaporated under reduced pressure and dried to obtain crude product 5a-t which was further purified by recrystallization in ethanol to afford pure compounds.

The synthetic route of 1-Methyl-1H-pyrazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference of 25016-11-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1 : methyl 14-cvclohexyl-6-f(l -methyl- 1 H-pyrazol-4-yl )methyl]-5.6.7, 8-tetrahvdroindolo[2, 1 – a] [2,5 Jbenzodiazocine-] 1 -carboxylate; To a solution of methyl 14-cyclohexyl-5,6,7,8-tetrahydroindolo[2,l-a][2,5]-benzodiazocine-l l- carboxylate (prepared as described in Example 48, Step 3) in MeOH (0.06 M), 1 -methyl- lH-pyrazole-4- carbaldehyde (3 eq) was added and the pH adjusted to pH 4 with acetic acid. The solution was stirred at RT for 30 mins before addition of NaBH3CN (1.5 eq). The reaction was stirred at RT for 16 h. The reaction was quenched with saturated aqueous NaHCO3 and extracted with EtOAc (x2). The combined organics were washed with brine, dried (Na2SO1O, filtered and concentrated in vacuo to give the title compound as a viscous oil (quantitative); MS (ES+) m/z 483 (M+H)+

The synthetic route of 1-Methyl-1H-pyrazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Related Products of 25016-11-9, 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 25016-11-9 as follows.

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[(S)-hydroxy(1-oxidopyridin-2-yl)methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (200 mg) and 4-formyl-1-methylpyrazole (0.4 g) in 1,2-dichloroethane (10 ml) were added sodium triacetoxyborohydride (0.22 g) and acetic acid (1 droplet) at room temperature and the mixture was stirred for 5 days. To the reaction solution was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (ethanol:ethyl acetate 1:3 ? 1:2) and recrystallized from ethyl acetate-diisopropylether to give 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[(S)-hydroxy(1-oxidopyridin-2-yl)methyl]phenyl]-1-(1-methylpyrazol-4-ylmethyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 87) (96.1 mg) as yellow crystals. m.p. 94 to 97C 1H-NMR (200 MHz, CDCl3) delta 0.93 (3H, t, J = 7.1 Hz), 1.32 to 1.46 (2H, m), 1.51 to 1.68 (2H, m), 2.80 to 2.89 (2H, m), 3.29 to 3.39 (2H, m), 3.55 (2H, t, J = 6.6 Hz), 3.81 (2H, t, J = 5.0 Hz), 3.90 (3H, s), 4.16 (2H, t, J = 5.0 Hz), 4.44 (2H, s), 6.07 (1H, d, J = 4.4 Hz), 6.43 (1H, d, J = 4.4 Hz), 6.91 to 7.00 (4H, m), 7.24 to 7.28 (2H, m), 7.32 (1H, s), 7.38 to 7.63 (8H, m), 7.62 to 7.67 (3H, m), 8.24 to 8.28 (1H, m). IR (KBr) 3274, 1653, 1605, 1516, 1499, 1433, 1404, 1316, 1240, 1184, 1123, 818 cm-1 Elemental Analysis for C40H43N5O5¡¤0.75H2O Calcd. C, 69.90; H, 6.53; N, 10.19: Found. C, 69.98; H, 6.77; N, 9.90.

According to the analysis of related databases, 25016-11-9, the application of this compound in the production field has become more and more popular.

Synthetic Route of 25016-11-9, 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 25016-11-9 as follows.

Intermediate 69 (600mg, 1 eq.) was dissolved in tetrahydrofuran, and lithium aluminum hydride (210 mg, 1 eq.) was added under ice bath and the mixture was reacted at room temperature for 2 h. After completion of the reaction, 210 mul of water, 210 mul of 10% aqueous sodium hydroxide solution, and 630 mul of water were successively added, followed by addition of anhydrous magnesium sulfate. The mixture was stirred for a while, filtered and evaporated to dryness to give 400 mg of an oil. MS (ESI): 113(M+H)

According to the analysis of related databases, 25016-11-9, the application of this compound in the production field has become more and more popular.