Category: 17289-26-8

Related Products of 17289-26-8, These common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-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.

Step 1: Synthesis of 4-ethynyl-1-methyl-1H-imidazole A solution of l-methyl-1H-imidazole-4-carbaldehyde (2 g, 1 eq) in MeOH (180 ml) was cooled at 0 C. K2CO3(5.02 g, 2 eq) and dimethyl (1-diazo-2-oxopropyl)phosphonate (7.7 g, 2.2 eq) was added. The mixture was stirred for 4 hr at 0 C., and extracted with dichloromethane and water. The organic layer was washed with sat. aq. NH4Cl, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified with column chromatography to prepare the title compound (1.2 g, 62%). 1H NMR (600 MHz, CDCl3-d1); delta7.60 (s, 1H), 7.32 (m, 1H), 3.37 (s, 3H), 3.48 (s, 1H). MS (ESI, m/z): 107.1 [M+H]+.

Statistics shows that 1-Methyl-1H-imidazole-4-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 17289-26-8.

Synthetic Route of 17289-26-8,Some common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-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.

General procedure: The L-Proline or L-tert-Leucine-based amine was dissolved in DCM (2 M), followed by the additionof the imidazole based aldehyde (1-1.3 equiv.) and MgSO4H2O (1 g/5 mL solvent). The mixture wasstirred overnight at room temperature. Afterwards, solids were removed by filtration and the resultingsolution was concentrated in vacuo. The residue was dissolved in MeOH (2 M) and the solution wascooled to 0 C. NaBH4 (3 equiv.) and a catalytic amount of conc. HCl were added to this solution. Themixture was stirred for 30 min at 0 C, and 1 h at room temperature; after this period, an equal volumeof saturated NaHCO3 solution was added to quench the reaction. After washing with DCM and brine,the organic phase was separated, dried over anhydrous Na2SO4 and concentrated in vacuo to afford theraw product. Purification of the resulting raw material was carried out via column chromatography usingDCM and MeOH, eluted compound might be subsequently recrystallized from DCM and pentane.

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-4-carbaldehyde, its application will become more common.

Adding a certain compound to certain chemical reactions, such as: 17289-26-8, name is 1-Methyl-1H-imidazole-4-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 17289-26-8, category: imidazoles-derivatives

To a solution of 15 (1.01 g, 9.18 mmol) in dry THF (10 mL) were added 5a (3.35 g. 10.1 mmol, 1.1 eq)and TMG (1.7 mL, 13.8 mmol, 1.5 eq) at 0 C, and the mixture was stirred for 24 h at rt. The reaction mixture was quenched with water and acidified with 1N aqueous HCl, and extracted with CH2Cl2. The aqueous layer was neutralized with sat. aqueous NaHCO3 and extracted with CH2Cl2. The combined organic extracts wered ried over anhydrous MgSO4, concentrated in vacuo to afford the crude product. The residue was purified by silica gel flash column chromatography (40:1 CHCl3 / MeOH). The obtained residue was washed with Et2O and the cake was dried in a house vacuum oven to afford 11a (1.90 g, 65%) as a white solid. IR (solid, cm-1) 1063, 1225, 1273, 1462, 1728, 2951, 32291H NMR (500 MHz, CDCl3) delta 3.68 (s, 3H), 3.79 (s, 3H), 5.18 (s, 2H), 6.56 (s, 1H), 6.95 (s, 1H), 7.31-7.43 (m,6H)13 C NMR (125 MHz, CDCl3) delta 33.5, 52.2, 67.1, 112.9, 121.4, 126.6, 128.0, 128.1, 128.4, 136.2, 137.7, 154.1,165.8FAB-MS : m/z 316 (M+H)+HRMS (ESI) Calculated for C16H18N3O4 316.1291 Found 316.1299

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-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

These common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-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. HPLC of Formula: C5H6N2O

2-Amino-5-methyl-4-phenylthiophene-3-carboxamide 123 (1.0 eq) was refluxed with 1-methylimidazole-4-carboxaldehyde (1.1 eq) in acetic (5 mL) acid for 24h. After completion of the reaction (confirmed by TLC), solution was cooled and diluted with water. The precipitate was filtered off and dried to give compound 126 (Yield -87%) as a brown solid. The scale was calculated on 700 mg theoretical yield of product. Yield: 609 mg (87 %).

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

Electric Literature of 17289-26-8, A common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-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.

14.1 Methyl (E) -3- (l-methyl-lH-imidazol-4-yl) acrylate1 ml (5.5 mmol) of methyl diethylphosphonoacetate are added to a suspension of 220 mg (5.5 mmol) of sodium hydride at 60% in 5 ml of tetrahydrofuran cooled to 00C. After stirring for 1 h, 500 mg (4.5 mmol) of 1- methyl-lH-imidazole-4-carbaldehyde are added and the mixture is stirred for 4 hours at ambient temperature and then hydrolysed with water and extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over magnesium sulphate, filtered and evaporated. The product obtained is precipitated from heptane and filtered. 430 mg of methyl (E) -3- (1-methyl-lH-imidazol- 4-yl) acrylate are obtained in the form of a yellow powder with a yield of 57%.

The synthetic route of 17289-26-8 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 17289-26-8, 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. 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

190c) (Z)-tert-Butyl 3-(1 -methyl- -imidazol-4-yl)acrylate To a solution of tert-butyl 2-(diethoxyphosphoryl)acetate (9.62 g, 38.1 mmol) in tetrahydrofuran (THF) (50 mL), sodium hydride (1 .831 g, 45.8 mmol) was added. The reaction mixture was stirred at 0 C under N2 for 10 mins. Then a solution of 1 -methyl- 1 H-imidazole-4-carbaldehyde (4.2 g, 38.1 mmol) in THF (50 mL) was added and the reaction mixture was stirred at 0 C for 150 mins. Water (100 mL) was added and extracted with ethyl acetate (3x). The organic layer was washed with water (2x) and brin (2x), dried over Na2S04 and concentrated. The crude product was purified on silica gel chromatography (hexane:ethyl acetate :TEA= 1 :1 :0.01) to afford the title compound (Z)- tert-butyl 3-(1 -methyl-1 H-imidazol-4-yl)acrylate (6.1 g, 28.7 mmol, 75 % yield) as colorless oil. LC-MS m/z 201 .1 (M+H)+, 1 .72 min (ret. time).

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-imidazole-4-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; CALLAHAN, James Francis; KERNS, Jeffrey K.; LI, Peng; LI, Tindy; MCCLELAND, Brent W.; NIE, Hong; PERO, Joseph E.; DAVIES, Thomas Glanmor; GRAZIA CARR, Maria; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; VERDONK, Marinus Leendert; WOOLFORD, Alison Jo-Anne; WILLEMS, Hendrika Maria Gerarda; (664 pag.)WO2017/60854; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-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-imidazole-4-carbaldehyde

A 10 litre round bottomed flask fitted with an overhead stirrer with a large paddle was charged with 5- bromo-2-(4-chlorobenzoyl)-3-fluorobenzoic acid (178.25 g; 0.5 mol) and anhydrous THF (2610 mL) added. This solution was cooled to -5CPatent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; CHESSARI, Gianni; HOWARD, Steven; BUCK, Ildiko Maria; CONS, Benjamin David; JOHNSON, Christopher Norbert; HOLVEY, Rhian Sara; REES, David Charles; ST. DENIS, Jeffrey David; TAMANINI, Emiliano; GOLDING, Bernard Thomas; HARDCASTLE, Ian Robert; CANO, Celine Florence; MILLER, Duncan Charles; CULLY, Sarah; NOBLE, Martin Edward Maentylae; OSBORNE, James Daniel; PEACH, Joanne; LEWIS, Arwel; HIRST, Kim Louise; WHITTAKER, Benjamin Paul; WATSON, David Wyn; MITCHELL, Dale Robert; (293 pag.)WO2017/55860; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 17289-26-8, A common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-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.

[00215] Examples 22 and 33 were synthesized via parallel synthesis according to the following method. To each microwave vial containing an aldehyde (0.08 mmol) corresponding to the R3 group contained in Examples 13-36 was added MeOH (0.65 mL) and CH3NH2 (2.0 M in THF; 0.04 mL, 0.08 mmol). The reaction mixtures were heated to 60 C for 10 min using microwave irradiation, then cooled to rt. To each reaction mixture was added a 0.24 M solution of Intermediate 5 in MeOH (0.22 mL, 0.05 mmol). The resulting reaction mixtures were heated to 100 C for 20 min using microwave irradiation. After cooling to rt, they were diluted with MeOH (0.25 mL). Examples 22 and 33 were purified from their corresponding solutions by RP preparative HPLC using Method H. HPLC/MS data for each compound was collected using Method E, and the molecular masses of the compounds were determined by MS (ES) by the formula m/z. Both the retention time and MS data are listed in Table 2.

The synthetic route of 17289-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ABELL, Lynn; ADAM, Leonard; CAVALLARO, Cullen L.; FINLAY, Heather; FRIENDS, Todd J.; HANGELAND, Jon J.; JIANG, Ji; LAWRENCE, R. Michael; LLOYD, John; PI, Zulan; TORA, George O.; QIAO, Jennifer X.; HU, Carol Hui; WANG, Tammy C.; WO2013/48982; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 17289-26-8,Some common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-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.

To a solution of OI-14a (4 g, 36.36 mmol, 1.0 eq) in chloroform (40 mL) was added NBS (7.12 g, 40 mmol, 1.1 eq). The mixture was stirred at 70 C. for 3 h. Then the mixture was cooled to room temperature and diluted with a saturated aqueous solution of Na2CO3 (50 mL) and DCM (100 mL). The organic layer washed with brine and water, dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give OI-14b (333 mg, 4.8%).

The synthetic route of 17289-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Foresee Pharmaceuticals Co., Ltd.; YANG, Wenjin; CHANG, Kai-Wei; LIU, Suying; TSAI, Cheng-Han; (98 pag.)US2019/352288; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem