Category: 177760-04-2

These common heterocyclic compound, 177760-04-2, name is Ethyl 2-amino-1-methyl-1H-imidazole-5-carboxylate, 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. Formula: C7H11N3O2

To a solution of sodium nitrite (18.3 g, 266 mmol) in water (55 mL)cooled around 5 C in an ice-salt bath, was added dropwise asolution of the amino ester 4 (6.42 g, 38.0 mmol) in acetic acid (42 mL). The temperature was allowed to rise gradually to rt and the reaction mixture was stirred overnight. The reaction mixturewas extracted with dichloromethane (3 50 mL). The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using cyclohexane/ethyl acetate (7/3,v/v) as eluent. After concentration under vacuum, the residue was washed with water (2 50 mL). The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure to yield nitro ester 5 as yellow crystals (5.67 g, 28.5 mmol). Yield 75%; mp 56-58 C (Lit. 56-58 C [40] and 65-66 C [37]); Rf 0.40(SiO2, cyclohexane/ethyl acetate, 7/3, v/v); IR (ATR) n cm1 1723,1552, 1486, 1519, 1364, 1233, 767; 1H NMR (CDCl3, 300 MHz) delta 7.70(s, 1H, CHAr), 4.39 (q, 2H, 3J 7.1 Hz, OCH2CH3), 4.31 (s, 3H, NCH3),1.39 (t, 3H, 3J 7.1 Hz, OCH2CH3); 13C NMR (DMSO-d6, 126 MHz) delta 158.71 (CO), 147.61 (CArNO2), 133.70 (CHAr), 126.07 (CArCO), 61.34(OCH2), 35.14 (NCH3), 13.91 (CH2CH3).

The synthetic route of Ethyl 2-amino-1-methyl-1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

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

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. 177760-04-2, name is Ethyl 2-amino-1-methyl-1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 177760-04-2

A solution of the amino ester (36.94 g, 0.218 mol) in 200 ml of acetic acid was added drop wise to a solution of sodium nitrite (100 g, 1.449 mol) and water (300 ml) cooled in an ice-water bath, and stirred. The temperature of the reaction mixture, which was measured to be around -5 – 1O0C was raised to rt and and the reaction mixture stirred overnight. The reaction mixture was extracted with DCM (3 x 150 mL). The combined DCM layers were dried and evaporated to yield a reddish residue which was separated by column chromatography on silica gel employing as eluent EA/hexane (30%) to yield 1-N- methyl-2-nitroimidazole-5-carboxylic acid ethyl ester (“nitro ester”) as a light brown solid (27 g, yield 62%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 177760-04-2.

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

Application of 177760-04-2, 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. 177760-04-2, name is Ethyl 2-amino-1-methyl-1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Aminoimidazole (0.700 g, 4.14 mmol) in acetic acid (7.3 mL) was added dropwise to an aqueous solution of sodium nitrite (3.6 mL, 11 M). The solution was stirred at room temperature for 4 h until no more N2 was formed. The reaction mixture was extracted with CH2Cl2 (1 x 20 mL), washed with brine (1 x 20 mL) and a saturated aqueous solution of Na2SO3 (1 x 20 mL). The organic layer was then dried over Na2SO4, filtered and concentrated to afford a crude yellow solid. Purification by flash chromatography using a prepacked 25 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 7%A / 93%B (4 CV), 7%A / 93%B ? 60%A / 40%B (10 CV), 60%A / 40%B (2 CV); flow rate: 70 mL/min; monitored at 254 and 280 nm] afforded the nitroimidazole analogue 27 (0.510 g, 2.60 mmol, 63%) as a yellow solid.1H NMR (600 MHz, CDCl3) delta 7.74 (1H, s), 4.40 (2H, q, J = 7.1 Hz), 4.35 (3H, s), 1.41 (3H, t, J = 7.1 Hz).13C NMR (151 MHz, CDCl3) delta 159.08, 147.46, 134.67, 126.29, 61.84, 35.39, 14.18.

The synthetic route of Ethyl 2-amino-1-methyl-1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Winn, Blake A.; Shi, Zhe; Carlson, Graham J.; Wang, Yifan; Nguyen, Benson L.; Kelly, Evan M.; Ross, R. David; Hamel, Ernest; Chaplin, David J.; Trawick, Mary L.; Pinney, Kevin G.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 636 – 641;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem