Category: 39070-14-9

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 39070-14-9 as follows. Safety of (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol

General procedure: To a solution of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (6) (1 eq.) in freshly distilled anhydrous THF (10?mL for 3?mmol of alcohol 6) was added dropwise lithium bis(trimethylsilyl)amide (1?M in THF, 1.1 eq.) at -78?C under an inert atmosphere. The reaction mixture was stirred around 5?min?at -78?C, and a solution of bis(2-chloroethyl)phosphoramidic dichloride (8) (1.1 eq.) in THF (3.3?mmol in 10?mL), previously cooled at -78?C, was added all at once at the same temperature (T0). The reaction mixture was stirred for 15-80?min, before the addition of a solution of the appropriate amine 18-22 (2-2.2 eq.) in THF (3?mL for 5?mmol of amine) and stirring was maintained at -78?C for 5?min to 75?min. These reaction times were determined by 31P NMR monitoring for each compound. The reaction was stopped by addition of water (20?mL for 3?mmol of alcohol 6), concentrated in vacuum and then extracted with EtOAc (3?*?50?mL for 3?mmol of alcohol 6). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using an eluent gradient (EtOAc/EtOH with TEA or NH4OH) to afford compounds 23-27 as yellow to orange oils.

According to the analysis of related databases, 39070-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, 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. category: imidazoles-derivatives

2,4-Dichloro-phenol (190 mg, 1.17 mmol) is dissolved in methylene chloride (2 mL). To the solution is added (3-methyl-2-nitro-3H-imidazol-4-yl)-methanol (115 mg, 0.732 mmol) and triphenylphosphine (211 mg, 0.805 mmol). The mixture is stirred at room temperature until a solution is achieved. The solution is then cooled in an ice bath and treated with diisopropyl azodicarboxylate, DIAD (158 xL, 0.805 mmol). After 1 hour the ice bath is removed and the mixture is stirred overnight at room temperature. Crude product is purified on a silica gel column to isolate the product mixed with triphenylphosphine oxide. The solids are triturated with t-butyl methyl ether to remove the triphenylphosphine oxide to afford 5-(2,4-dichloro- phenoxymethyl)-l-methyl-2-nitro-lH-imidazole. MS (ESI+) for C11H9Cl2N3O3m/z 301.1 (M+H)+.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENCIA CORPORATION; KHAN, Shaharyar; (80 pag.)WO2018/129258; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39070-14-9, 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 39070-14-9 as follows.

A mixture of 2-(1-methyl-5-nitro-1H-imidazol-2-yl)-ethanol (1.32 mmol) and 1-fluoro- 3 -nitrobenzene (1.67 mmol) and K2C03(465 mg, 3.36 mmol) in DMF (5 mL) was stirred 2 hours at ambient temperature followed by heating. The reaction was worked-up by extraction. The residue was purified by prep-HPLC with the following condition: column: XBridge preparative CI 8 OBD column 19x 150 mm, 5 um; mobile phase A: water (10 mmol/L NH4HCO3), mobile phase B: ACN; flow rate: 20 mL/min; gradient elution. The product-containing fractions were collected and then lyophilized to give l-methyl-5-nitro-2-(3-nitro-phenoxymethyl)-lH- imidazole. LC-MS: (ES, m/z) 279.07 (M+H)+; analysis: C, 47.53; H, 3.69; N, 20.24; O, 28.85.

According to the analysis of related databases, 39070-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENCIA CORPORATION; KHAN, Shaharyar; (80 pag.)WO2018/129258; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 39070-14-9, A common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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.

To a suspension of bis(2-chloroethyl)ammonium chloride (1.43 g, 8.01 mmol) in dichloromethane (DCM) phosphorus trichloride (0.32 ml, 3.64 mmol) was added at rt followed by addition of TEA (3.05 ml, 21.84 mmol). The reaction mixture was stirred at rt for 30 minutes and then N-methyl 2-nitroimidazolyl methanol (0.474 g, 3.31 mmol) in DME was added. After stirring for 0.5 hour, the reaction mixture was cooled to -2O0C and tert- butyl hydroperoxide (0.7 ml, 3.82 mmol, 5.5 M in Decane) was added. The reaction mixture was warmed to rt over a period of one hour, and poured into 10% aqueous HCl. The organic layer was separated and the aqueous layer was extracted with DCM. The combined organic solution was dried with MgSO4 and concentrated to yield a residue which was purified by flash chromatography with 6-12% methanol in DCM yielding 6.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; WO2007/2931; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem