Category: 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, Product Details of 39021-62-0

To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (3.0 g, 6.97 mmol, Intermediate 5: 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 then 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 to dryness. Chromatography on silica gel (30% acetone-DCM increasing to 5% MeOH) provided the title compound.

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-imidazole-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

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.; (53 pag.)US2017/258782; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature 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.

Scheme 1; tert-Butyl (2-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-5- yl)methyl(2-methoxyethyl)carbamate (46); Step 1. 5-alpha.3-Dioxan-2-yl)-1-methyl-1H-imidazole (38) [Shafiee A., Rastkary N., Jorjani M., Shafaghi B., Arch.Pharm.Pharm.Med.Chem. 2002, 2, 69-76]; To a solution of 1 -methyl- 1 H- 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).

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; METHYLGENE INC.; WO2009/26717; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39021-62-0, 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.

n-BuLi (2.5 M in hexanes, 0.52 mL, 1.3 mmol) was added dropwise to a solution of 6-bromo-2,4-dichloro-3-(2-chlorophenyl)quinolone (387.5 mg. 1 mmol, Intermediate 2: step c) in dry THF (10 mL) in a 100 mL three necked round bottomed flask at -78 C. under N2. Stirring was continued for 30 minutes then a solution of 1-methyl-1H-imidazole-5-carbaldehyde (110 mg, 1 mmol) in dry THF (10 mL) was added at -78 C. The cooling bath was removed and the mixture was gradually warmed to room temperature and stirred for 2 hours. The mixture was quenched by adding H2O (10 mL) and then extracted with CH2Cl2 (2*50 mL). The combined organic phase was dried over Na2SO4, concentrated to dryness and purified by prep-TLC (developed by CH3OH/CH2Cl2 1:40) to afford the title compound as a white solid. MS (ESI): 418.1 [M+H]+. 1H NMR (300 MHz, CD3OD) delta ppm 8.47 (s, 1H), 8.06 (d, J=8.6 Hz, 1H), 7.98-7.84 (m, 1H), 7.68-7.34 (m, 5H), 6.57 (d, J=3.3 Hz, 1H), 6.17 (s, 1H), 3.71 (s, 3H).

The synthetic route of 1-Methyl-1H-imidazole-5-carbaldehyde has been constantly updated, and we look forward to future research findings.

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

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., Recommanded Product: 39021-62-0

Example 2: (2,4-Dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanoln-BuLi (2,5 M in hexanes, 0,52 mL, 1 .3 mmol) was added dropwise to a solution of 6-bromo-2,4-dichloro-3-phenylquinoline (353 mg, 1 mmol, intermediate 1 : step c) in dry THF (10 mL) in a 100 mL three necked round bottomed flask at -78 C under N2. Stirring was continued for 30 minutes then a solution of 1-methyl-1H-imidazole-5-carbaldehyde (110 mg, 1 mmol) in dry THF (10 mL) was added at -78 C. The cooling bath was removed and the mixture was gradually warmed up to room temperature and stirred for 2 hours. The mixture was quenched by adding H2O (10 mL) and then extracted with CH2Cl2 (2 x 50 mL). The combined organic phase was dried over Na2SO4, concentrated to dryness and purified by prep-TLC (developed by CH3OH/CH2Cl2 1 :5) to afford the title compound as a white solid. MS (ESI): 384.1 [M+H]+. 1H NMR (300 MHz, CD3OD) delta ppm 8.45 (s, 1H), 7.94 (dd, J = 42.2, 8.0 Hz, 2H), 7.73-7.24 (m, 6H), 6.56 (s, 1H), 6.16 (s, 1H), 3.70 (s, 3H).

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

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.; WO2015/57206; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 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.

EXAMPLE 6A 1-(1-methyl-1H-imidazol-5-yl)-3-phenylprop-2-yn-1-ol A suspension of 1-methyl-1H-imidazole-5-carbaldehyde (prepared according to the procedure described in J. Org. Chem. 1993, 58, 1159-1166, 170 mg, 1.55 mmol) in dioxane (10 mL) was treated with 1M phenylethynylmagnesium bromide in THF (7.73 mL, 7.73 mmol), heated to 80 C. for 1 hour, cooled to room temperature, treated with brine, and extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 2% methanol/ethyl acetate with 0.2% NH4OH to provide the desired product (210 mg, 64%). MS (DCI/NH3) m/e 213 (M+H)+; 1H NMR (300 MHz, CDCl3) delta7.52 (s, 1H), 7.47 (m, 2H), 7.34 (m, 3H), 7.15 (s, 1H), 5.74 (s, 1H), 3.83 (s, 3H).

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-imidazole-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gwaltney II, Stephen L.; Nelson, Lissa T.J.; O’Connor, Stephen J.; Sham, Hing L.; Sullivan, Gerard M.; Wang, Weibo; US2003/216441; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 39021-62-0, 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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

A 20 mL vial equipped with a stir bar was charged with the recovered amine 62 and product mixture (0.330 mmol, 1 equiv.), 43.3 mg of l-methyl-lH-imidazole-4-carbaldehyde (0.390 mmol, 1.2 equiv.), 0.019 mL of CH3COOH (0.330 mmol, 1 equiv.) and 3.4 mL of CH2CI2 and stirred at rt for 3 h. Then 111 mg of NaBH(OAc)3 (0.520 mmol, 1.6 equiv.) was added. After stirring at rt for 12 h, the reaction mixture was quenched by addition of sat. NaHCCb solution and sat. Na2CCb sol., and the product was extracted with CH2CI2 (3x) and dried over Na2S04. The crude product was purified on silica gel column (12 g) using 0-30 % MeOH in EA as eluent affording 116 mg (43%) of N-((S)-3-((R)-3-(((4-(l,3-dioxoisoindolin-2-yl)butyl)((S)-5,6,7,8-tetrahydroquinolin-8- yl)amino)methyl)-4-((1 -methyl- lH-imidazol-5-yl)methyl)piperazin- 1 -yl)- 1 -phenylpropyl)-4,4- difluorocyclohexane-l -carboxamide 78 as a yellowish foam.

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; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; ALTAS TAHIROVIC, Yesim; WILSON, Lawrence; PELLY, Stephen Christopher; (102 pag.)WO2019/183133; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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, Product Details of 39021-62-0

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]+.

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.

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

Application of 39021-62-0, These common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-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.

Under N2 at -78 100 mL 3-neck round bottom flask at nBuLi (hexane of 2.5 M, 0.52 mL, 1.3 mmol) to dry THF (10 mL) of 6-bromo-2,4-dichloro-3 – phenyl quinoline (353 mg, 1 mmol, intermediate 1: step c) was added dropwise to a solution of. Continuous stirring for 30 minutes, was added a solution of dry THF (10 mL) of 1-methyl -1H- imidazole-5-carbaldehyde (110 mg, 1 mmol) at -78 . The cooling bath was removed and was gradually The mixture was warmed to RT, stirred for 2 hours. The mixture was then quenched by the addition of H2O (10 mL), extracted with CH2Cl2 (2 × 50 mL). Dry the combined organic phases with Na2SO4 and concentrated to dryness, prep-TLC: Purification of (CH3OH / CH2Cl2 1 evolves to 5) to give the title compound as a white solid.

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:
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

Reference of 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.

General procedure: A solution (0.05mol-%) of the appropriate furan-2-one (1 eq.) in dry diethyl ether (DEE) was mixed with the N-heterocyclic carbaldehyde (1, 2 or 3 eq.) under a nitrogen atmosphere at 0C. After stirring for 30min, excess dry diethylamine (4 eq.) was added dropwise. Stirring was continued for 30min. The solution was allowed to warm up over night and the product usually precipitated as fluffy powder. The precipitate was washed with cold DEE and dried in vacuo.

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

Reference:
Article; Uhrner, Fabian; Lederle, Felix; Namyslo, Jan C.; Gjikaj, Mimoza; Schmidt, Andreas; Huebner, Eike G.; Tetrahedron; vol. 73; 30; (2017); p. 4472 – 4480;,
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.

N-(4-Fluorobenzyl)-3-hydroxy-10-(((4-((1-methyl-1H-imidazol-5-yl)methyl)-1-piperazinyl)(oxo)acetyl)amino)-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide. To a solution of 7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide, 10-[[1,2-dioxo-2-(1-piperazinyl)ethyl]amino]-N-[(4-fluorophenyl)methyl]-4,6,7,8,9,10-hexahydro-3-hydroxy-4-oxo- (0.025 g, 0.040 mmol) in 1,2-dichloroethane (1 mL) and diisopropyl ethylamine (6.97 muL, 0.040 mmol) cooled to 0 C. was added 1-methyl-1H-imidazole-5-carbaldehyde (4.39 mg, 0.040 mmol) and the mixture stirred at 0 C. for 15 min. Acetic acid (2.284 muL, 0.040 mmol) and sodium triacetoxyborohydride (9.30 mg, 0.044 mmol) were added and the mixture stirred at room temperature for 4 h. The solvent was removed under a stream of air and the residue purified by preparative HPLC: Solvent A=10% methanol/90% H2O/0.1% trifluoroacetic acid; Solvent B=90% methanol/10% H2O/0-1% trifluoroacetic acid; Start % B=0; Final % B=100; Gradient time=15 min; Stop time=15 min; Column=Sunfire 19×100 mm, C18, 5 mum to give the title compound as a trifluoroacetic acid salt as a purple solid (14.7 mg, 49% yield). 1H NMR (500 MHz, MeOD) delta: 9.67 (1H, brs), 8.94 (1H, brs), 8.86 (1H, brs), 7.60 (1H, brs), 7.32-7.48 (2H, m), 7.03 (2H, t, J=8.39 Hz), 4.56 (2H, brs), 4.19 (2H, brs), 3.77-4.08 (4H, m), 3.50-3.77 (4H, m), 2.69 (3H, brs), 2.51 (1H, brs), 2.39 (2H, d, J=5.80 Hz), 2.21 (2H, brs), 1.96 (2H, d, J=4.88 Hz), 1.74 (2H, brs). (M+H) calcd for C30H36FN8O5: 607.27; found: 607.44.

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; US2009/253677; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem