Category: 39021-62-0

Related Products of 39021-62-0,Some common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-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.

-78 in N2under a 100 mL 3-neck round bottom flask in then-BuLi(hexane of 2.5 M, 0.52 mL, 1.3 mmol) to dry THF (10 mL) of 6-bromo-2,4-dichloro- 3- (2-chlorophenyl) quinolone (387.5 mg, 1 mmol, intermediate 2: step c) was added dropwise to a solution of.30 bungan continuous stirring, and then the, -78 in dry THF (10 mL) of 1-methyl -1H-imidazole-5-carbaldehyde(110 mg, 1 mmol) was added to the solution.The cooling bath was removed and was gradually The mixture was warmed to RT, stirred for 2 hours.The mixture H2next quenched by the addition of O (10 mL), CH2Cl2and extracted with (2 ¡Á 50 mL).The combined organic phases Na2SO4dried and concentrated dry, prep-TLC (CH3OH / CH2Cl2to give evolves to 1:40) to give the title compound as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-5-carbaldehyde, its application will become more common.

Reference:
Patent; Janssen Pharmaceuticals N.V; Leonardo, Christi.A.; Barvei, Kent; Edward, James P.; Gloita, Kevin D.; Kummer, David .A.; Maharoof, Umar; Nishimura, Rachael; Urbanski, Mode; Venkatesan, Hariharan; Wang, Ai Hua; Olin, Ronald L.; Woods, Craig; Fourier, Anne; Shu, Jih; Cumings, Maxwell D.; (86 pag.)KR2016/68948; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 1-Methyl-1H-imidazole-5-carbaldehyde

A mixture of D100 (30.mg, 0.09mmol) and 1-methyl-1H-imidazole-5-carbaldehyde (52mg,0.47mmol) in IPA (2mL) was treated with 4N HCl in dioxane (22.5uL, 0.61mmol) and heated at70C for 5min. Solvent was removed in vacuo and the residue purified by preparative HPLC(HzO,CH3CN 0.1% HCOOH, giving the title compound E37 (17mg) as white solid. Method 3; Rt:2.54min. m/z: 438.11 (M+Ht. 1H NMR (300 MHz, DMSO-d6) 8 ppm 3.70 (s, 3 H) 6.08 (br d,1=7.79 Hz, 1 H) 7.08 (d, 1=8.89 Hz, 1 H) 7.18 (s, 1 H) 7.64- 7.84 (m, 3 H) 7.96 (dd, 1=8.80, 2.02Hz, 1 H) 8.18 (br s, 2 H) 8.32 (d, 1=1.83 Hz, 1 H) 10.44 (s, 1 H)

The synthetic route of 39021-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSPEDALE SAN RAFFAELE S.R.L.; IRBM S.P.A.; PROMIDIS S.R.L.; ISTITUTO NAZIONALE DI GENETICA MOLECOLARE – INGM; DE FRANCESCO, Raffaele; DONNICI, Lorena; GUIDOTTI, Luca; IANNACONE, Matteo; DI FABIO, Romano; SUMMA, Vincenzo; BENCHEVA, Leda Ivanova; DE MATTEO, Marilenia; FERRANTE, Luca; PRANDI, Adolfo; RANDAZZO, Pietro; (238 pag.)WO2020/16434; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 39021-62-0,Some common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-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.

To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (3.0 g, 6.97 mmol, Intermediate 10: step d) was added THF (40 ml) and the solution was cooled to -70 C. n-BuLi (2.5 M in hexanes, 2.8 mL, 7 mmol) was added dropwise. After 2 minutes, 1-methyl-1H-imidazole-5-carbaldehyde (1.2 g, 9 mmol, in 10 mL THF) was introduced. After 15 minutes, the dry-ice bath was replaced with a 0 C. bath. After 35 minutes the reaction mixture was quenched with aqueous NH4Cl solution and the aqueous portion was extracted with EtOAc:THF (10:2) 5*50 mL. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Chromatography on silica gel (30% acetone-DCM increasing to 5% MeOH) provided the title compound. 1H NMR (500 MHz, CDCl3) delta ppm 8.21 (s, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.60 (dd, J=8.6, 1.9 Hz, 1H), 7.50 (d, J=8.2 Hz, 2H), 7.39 (d, J=8.1 Hz, 2H), 7.33 (s, 1H), 6.65 (s, 1H), 6.04 (s, 1H), 4.34 (s, 2H), 4.07 (s, 3H), 3.55 (s, 3H). MS (ESI): mass calcd. for C23H19ClF3N3O2, 461.1, m/z found 462.1 [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 1-Methyl-1H-imidazole-5-carbaldehyde, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; US2015/105372; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Methyl-1H-imidazole-5-carbaldehyde

Example 18 rac-(3aR,14bR)-10-CyclohexyI-N7-(dimethylsulfamoyl)-13-methoxy-N3a,N3a- dimethyl-2-((l-methyl-lH-imidazol-5-yl)methyl)-l,2,3,14b-tetrahydroindolo[2,l~ a]pyrrolo[3,4-d][2]benzazepine-3a,7(4H)-dicarboxamide. 1 -Methyl- 1H-imidazole- 5-carbaldehyde (16.3 mg, 0.15 mmol) and then NaCNBH3 (9.3 mg, 0.15 mmol) were added to a slurry of rac-(3aR,14bR)- 10-cyclohexyl-N7-(dimethylsulfamoyl)- 13- methoxy-N3a,N3a-dimethyl-l,2,3,14b-tetrahydroindolo[2,1-alpha]pyrrolo[3,4-d][2]benzazepine-3a,7(4H)-dicarboxamide (30 mg, 0.049 mmol) in MeOH (2 mL). The reaction mixture was stirred at rt for 4h, diluted with THF (1 mL) and treated with additional 1 -methyl- 1H-imidazole-5-carbaldehyde (25 mg). The reaction mixture was stirred at rt for 16h, diluted with DMF (1 mL) and treated with additional NaCNBH3 (10 mg). The reaction mixture was stirred at rt for Id, diluted with MeOH, and purified by preparative HPLC (H2O/MeOH with 0.1% TFA buffer) to yield rac-(3aR,14bR)- 10-cyclohexyl-N7-(dimethylsulfamoyl)- 13-methoxy-N3a,N3a- dimethyl-2-((l -methyl- lH-imidazol-5-yl)methyl)-l ,2,3 , 14b-tetrahydroindolo[2, 1 – alpha]pyrrolo[3,4-d] [2]benzazepine-3a,7(4H)-dicarboxamide (20.2 mg, 0.029 mmol, 58% yield) as a white solid. 1H NMR (300 MHz, CD3OD) delta 1.25 – 1.65 (m, 4H), 1.77 – 2.23 (m, 7H), 2.66 (d, J= 10.6 Hz, IH), 2.94 – 3.07 (m, 2H), 3.05 (s, 6H), 3.10 – 3.35 (m, 6H), 3.51 (d, J= 15.0 Hz, IH), 3.58 (d, J= 15.0 Hz, IH), 3.64 (s, 3H), 3.79 (d,J = 10.6 Hz, IH), 3.91 (s, 3H), 4.04 (d, J= 15.0 Hz, IH), 4.15 (dd, J= 10.6, 7.7 Hz, IH), 4.52 (d, J= 15.0 Hz, IH), 7.06 – 7.15 (m, 3H), 7.41 (d, J= 8.4 Hz, IH), 7.65 (dd, J= 8.4, 1.5 Hz, IH), 7.95 (d, J= 8.4 Hz, IH), 8.03 (d, J= 1.5 Hz, IH), 8.55 (br s, IH). LCMS: m/e 702 (M+H)+, ret time 3.16 min, 4 minute gradient.

The synthetic route of 39021-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/120733; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – 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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, A new synthetic method of this compound is introduced below., Formula: C5H6N2O

Intermediate 80: step a (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanol To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifiuoromethyl)benzyl)quinoiine (Intermediate 12: step d, 3.0 g, 6,97 mmol) was added THF (40 ml) and the solution was cooled to -70 C. K-BuLi (2.5 M in hexanes, 2.8 mL, 7 mmol) was added dropwise. After 2 minutes, 1- methyl-lH-imidazole-5-carbaldehyde (1.2 g, 9 mmol, in 10 mL THF) was introduced. After 15 minutes, the dry-ice bath was replaced with a 0 C bath. After 35 minutes the reaction mixture was quenched with aqueous NH4CI solution and the aqueous portion was extracted with EtOAc:THF (10:2) 5 x 50 mL. The combined organics were washed with brine, dried over Na2S04, filtered and concentrated to dryness to give the title compound.

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.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39021-62-0, Adding a certain compound to certain chemical reactions, such as: 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, belongs to imidazoles-derivatives compound, 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 39021-62-0.

Step 1 A solution of 1-methyl-1H-imidazole-5-carbaldehyde (1.46 g, 13.26 mmol), (R)-2-methylpropane-2-sulfinamide (2.893 g, 23.87 mmol), and tetraethoxytitanium (10.89 g, 47.73 mmol) in THF (100 mL) was heated to 65 C. for 12 h. The reaction was cooled and poured onto water. The solids were filtered off, and the filtrate was extracted with EtOAc. The layers were separated, and the organic layer was concentrated. The resulting residue was purified by SiO2 eluting with a DCM/MeOH gradient (1.5 to 2% MeOH) to afford 1.444 g (51.1%) of (R,E)-2-methyl-N-((1-methyl-1H-imidazol-5-yl)methylene)propane-2-sulfinamide (128).

According to the analysis of related databases, 39021-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Array BioPharma Inc.; Blake, Jim; Chen, Huifen; Chicarelli, Mark; Gaudino, John; Gazzard, Lewis; Kintz, Sam; Mohr, Pete; Robarge, Kirk; Schwarz, Jacob; Zhou, Aihe; US2014/66453; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39021-62-0, 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 39021-62-0 as follows.

A mixture of (E)-4-(benzylideneamino) isobenzofuran-1(3H)-one (474 mg, 2 mmol) and 1-methyl-1H-imidazole-5-carbaldehyde (220 mg, 2 mmol) in ethyl propionate (20 mL) was cooled to 0 C. Then a solution of sodium ethoxide in ethanol [sodium (184 mg, 8 mmol) in ethanol (10 mL)] was added dropwise. After the addition, the mixture was stirred at room temperature for 3 hr. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (100 mL¡Á4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=5:1 to 3:7) to give ethyl 3-(1-methyl-1H-imidazol-5-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (170 mg, yield 23%). LC-MS (ESI) m/z: 376 (M+1)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 39021-62-0, and friends who are interested can also refer to it.

Reference:
Patent; LEAD THERAPEUTICS, INC.; US2010/35883; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39021-62-0, Name is 1-Methyl-1H-imidazole-5-carbaldehyde, 39021-62-0, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

General procedure: Into a round-bottom flask, equipped with a condenser and containing a suspension of 6 (2.0 mmol, 1 equiv) in ethanol (15 mL), was introduced the aldehyde (2.2 mmol, 1.1 equiv) and two drops of concentrated HCl. The reaction mixture was stirred and heated at 80 C for approximately 18 h. While cooling down the crude mixture in an ice bath, a precipitate was formed which was subsequently filtered off and washed with both water (2 ¡Á 10 mL) and cold ethanol (3 ¡Á 15 mL). The solid residue was then dried in vacuum at 60 C.

Statistics shows that 1-Methyl-1H-imidazole-5-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 39021-62-0.

Reference:
Article; Pevet, Isabelle; Brule, Cedric; Tizot, Andre; Gohier, Arnaud; Cruzalegui, Francisco; Boutin, Jean A.; Goldstein, Solo; Bioorganic and Medicinal Chemistry; vol. 19; 8; (2011); p. 2517 – 2528;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39021-62-0, A common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-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 solution of 2-(3 ,4-dimethoxyphenyl)-3 -i sopropyl -5 -(piperidin-4-yl)- 1 H-indole, HC1 (25 mg, 0.060 mmol) in DCM (0.5 mL) was neutralized by adding triethylamine drop wise (checked by pH paper). The solution was added to a vial containing i-methyliH-imidazole-5-carbaldehyde (9.95 mg, 0.090 mmol), acetic acid (0.01 ml, 0.175 mmol) at room temperature. The mixture was stirred at room temperature for 16 h. Sodium triacetoxyborohydride (19.15 mg, 0.090 mmol) was added to the reaction mixture and the mixture was stirred for another 6 h at room temperature. The reaction mixture was purified by reverse phase prep LCMS to provide 2-(3,4-dimethoxyphenyl)-3-isopropyl-5-(1 -((1 -methyl- 1H-imidazol-5-yl)methyl)piperidin-4-yl)- 1H-indole (1.27 mg, 4.34% yield,97.2% purity) as a pale solid. LC retention time = 1.734 mm [E]. MS (E) m/z: 473.2 (M+H).

The synthetic route of 39021-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; MUSSARI, Christopher P.; HAQUE, Tasir S.; POSS, Michael A.; LOMBARDO, Louis J.; MACOR, John E.; PASUNOORI, Laxman; KUMAR, Sreekantha Ratna; (296 pag.)WO2018/26620; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39021-62-0, The chemical industry reduces the impact on the environment during synthesis 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, I believe this compound will play a more active role in future production and life.

To a solution of 1 -methyl- lH-imidazole-5-carbaldehyde (2.9 g, 26.3 mmol) in toluene (20 mL) was added propane- 1 , 3 -diol (4.01 g, 52.7 mmol) and CSA (0.306g, 1.317 mmol) and the reaction mixture was heated to reflux with azeotropic removal of the evolved water for 24 hours. The reaction mixture was cooled to RT, diluted with DCM and washed with NaHCO3 solution. It was then dried over Na2SO4, filtered and concentrated. Purification by column chromatography (80% EtOAc in Hexane to EtOAc) afforded 38 (2.53 g, 57% yield) as a yellow oil which solidified on standing to a yellow solid. MS (m/z): 169.2 (M+H)

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-imidazole-5-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; METHYLGENE INC.; WO2009/109035; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem