Category: 149520-94-5

Electric Literature of 149520-94-5, The chemical industry reduces the impact on the environment during synthesis 149520-94-5, name is Ethyl 2-amino-1H-imidazole-5-carboxylate, I believe this compound will play a more active role in future production and life.

a) Ethyl 7-oxo-5,6,7,8-tetrahydroimidazo[l,2-a]pyrimidine-2-carboxylateEthyl 2-amino-lH-imidazole-4-carboxylate (6.45 mmol, 1 g) and triethyl- amine (10.04 mmol, 1.016 g) were suspended in dry ACN (30 ml) and cooled to 0 C. Acryloyl chloride (9.67 mmol, 0.875 g) dissolved in dry ACN (4 ml) was added dropwise. The resulting mixture was slowly warmed to RT and subsequently heated to 50 C for 16 h. The solvent was evaporated and the residue purified by flash chromatography. 0.358 g of the title compound was obtained. lH-NMR (400 MHz, CDC13): delta 1.37 (t, 3H), 2.92 (t, 2H), 4.18 (t, 2H), 4.37 (q, 2H), 7.40 (s, IH), 8.78 (bs, IH).

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, Ethyl 2-amino-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ORION CORPORATION; TOeRMAeKANGAS, Olli; WOHLFAHRT, Gerd; SALO, Harri; RAMASUBRAMANIAN, Rathna, Durga; PATRA, Pranab, Kumar; MARTIN, Arputharaj, Ebenezer; HEIKKINEN, Terhi; VESALAINEN, Anniina; MOILANEN, Anu; KARJALAINEN, Arja; WO2012/143599; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 149520-94-5, A common heterocyclic compound, 149520-94-5, name is Ethyl 2-amino-1H-imidazole-5-carboxylate, molecular formula is C6H9N3O2, 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.

The mixture of 2-amino-lH-imidazole-4-carboxylic acid ethyl ester (220 mg, 1.42 mmol, 1.0 eq), 3-chloro-6-chloromethyl-quinoline (301 mg, 1.42 mmol, 1.0 eq) and K2C03 ( 294 mg, 2.13 mmol, 1.5 eq) in DMF ( 8 mL) was stirred at 50 C overnight. The reaction mixture was diluted with water and extracted with EA. The combined organic layers was dried and concentrated. The resulting residue was purified by chromatography on a silica gel column (DCM/MeOH = 20/1, v/v) to give 2-amino-l-(3-chloro-quinolin-6- ylmethyl)-lH-imidazole-4-carboxylic acid ethyl ester (100 mg, 21%) and 2-amino-3-(3- chloro-quinolin-6-ylmethyl)-3H-imidazole-4-carboxylic acid ethyl ester (120 mg, 26%) as a yellow solid.

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; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 149520-94-5, name is Ethyl 2-amino-1H-imidazole-5-carboxylate, 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 149520-94-5, HPLC of Formula: C6H9N3O2

a) Ethyl 7-oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidine-2-carboxylate Ethyl 2-amino-1H-imidazole-4-carboxylate (6.45 mmol, 1 g) and triethylamine (10.04 mmol, 1.016 g) were suspended in dry ACN (30 ml) and cooled to 0 C. Acryloyl chloride (9.67 mmol, 0.875 g) dissolved in dry ACN (4 ml) was added dropwise. The resulting mixture was slowly warmed to RT and subsequently heated to 50 C. for 16 h. The solvent was evaporated and the residue purified by flash chromatography. 0.358 g of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): delta 1.37 (t, 3H), 2.92 (t, 2H), 4.18 (t, 2H), 4.37 (q, 2H), 7.40 (s, 1H), 8.78 (bs, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-amino-1H-imidazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ORION CORPORATION; Toermakaengas, Olli; Wohlfahrt, Gerd; Salo, Harri; Ramasurbamanian, Rathna Durga; Patra, Pranab Kumar; Martin, Arputharaj Ebenezer; Heikkinen, Terhi; Vesalainen, Anniina; Moilanen, Anu; Karjalainen, Arja; US2014/94474; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 149520-94-5, 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. 149520-94-5, name is Ethyl 2-amino-1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 2-amino-1H-imidazole-4-carboxylate (980 mg, 6.8 mmol) and tert- butyl 2-(2,4-dichloroben2ylidene)-3-oxobutanoate (2.03 g, 6.4 mmol) were dissolved in ethanol (15 mL) and the reaction was heated to 75 C for 16 h. The reaction was concentrated under reduced pressure to obtain a 10: 1 mixture (by EtaPLC) of 6-tert- butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine- 2,6-dicarboxylate and 6-tert~butyl 3-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8- dihydroimidazo[1,2-a]pyrimidine-3,6-dicarboxylate (3.07 g, 100% crude yield) as a yellow foam. A small amount of this mixture (350 mg) was purified by silica gel chromatography to obtain 6-tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8- dihydroimidazo[1,2-a]pyrimidine-2,6-dicarboxylate (190 mg, 54%) and 6-tert-butyl 3-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-diliydroimidazo[1,2-a]pyrimidine-3 ,6- dicarboxylate (19 mg, 5.4%) as white solids.[00249] For 2-isomer: 1H NMR (400 MHz, CDCl3) delta 10.19 (br s, 1H), 7.43 (d, J= 2.2 Hz, IH), 7.38 (s, 1H), 7.34 (d, J= 7.2 Hz, 1H), 7.21 (dd, J= 2.2, 7.2 Hz, 1H), 6.67 (s, 1H), 4.29 (m, 2H), 2.57 (s, 3H), 1.34 (t, J= 7.0 Hz, 3H), 1.26 (s, 9H).[00250] HPLC-MS Phenomenex LUNA C- 18 4.6 X 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 4.13 rnin, 98% homogeneity index. [00251] LCMS: Anal. Calcd. for C21H23Cl2N3O4451.11 found: 452.24 (M+H)+. [00252] For 3-isomer: 1H NMR (400 MHz, CDCl3) delta 11.72 (br s, 1H), 7.59 (d, J= 8.4 Hz, 1H), 7.50 (br s, 1H), 7.27 (d, J= 3.5 Hz, 1H), 7.18 (dd, J= 3.0, 8.4 Hz, 1H), 6.91 (s, 1H), 4.16 (m, 2H), 2.44 (s, 3H), 1.41 (s, 9H), 1.26 (t, J= 7.0 Hz, 3H). [00253] HPLC-MS Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 4.24 min, 99% homogeneity index.[00254] LCMS: Anal. Calcd. for C21H23Cl2N3O4451.11 found: 452.24 (M+H)+. [00255] To a stirred solution of 6-tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7- methyl-5,8-dmydroimidazo[1,2-a]pyrimidrne-2,6-dicarboxylate (191 mg, 0.42 mmol) in acetone (5 mL) was added KMnO4 (66 mg, 0.42 mmol). After 1 h, the reaction was filtered through celite and concentrated under reduced pressure. The resulting residue was diluted with CH2Cl2 and extracted with H2O (2x). The organic layer was dried EPO over MgSO4, concentrated under reduced pressure and recrystallized from EtOAc to obtain 6-tert-butyl 2-ethyl 5-(2,4-dicMorophenyl)-7-methylimidazo[1,2-a]pyrimidirie- 2,6-dicarboxylate (107 mg, 57%) as white crystals.[00256] To a stirred solution of 6-tert-butyl 3 -ethyl 5-(2,4-dichlorophenyl)-7- methyl-5,8-dihydroimidazo[l ,2-alpha]pyrimidine-3,6-dicarboxylate (19 mg, 0.04 mmol) in acetone (2 mL) was added KMnO4 (7 mg, 0.04 mmol). After 1 h, the reaction was filtered through celite and concentrated under reduced pressure. The resulting residue was diluted with CH2Cl2 and extracted with H2O (2x). The organic layer was dried over MgSO4, concentrated under reduced pressure and purified by silica gel chromatography to obtain 6-tert-butyl 3-ethyl 5-(2,4-dichlorophenyl)-7- methylimidazo[1,2-a]pyrimidine-2,6-dicarboxylate (14 mg, 74%) as white solid. [00257] For 2-isomer: 1H NMR (400 MHz, CDCl3) delta 7.68 (d, J= 1.8 Hz, 1H), 7.53 (s, 1H), 7.50 (dd, J= 1.8, 7.6 Hz, 1H), 7.35 (d, J= 7.6 Hz, 1H), 4.43 (m, 2H), 2.77 (s, 3H), 1.41 (t, J= 7.2 Hz, 3H), 1.29 (s, 9H). [00258] 13C NMR (500 MHz, CDCl3) 6 163.7, 162.7, 159.8, 147.0, 141.1, 138.5, 138.2, 134.5, 131.4, 130.3, 128.1, 127.8, 119.0, 114.1, 83.8, 61.4, 27.7, 24.3, 14.3. [00259] HPLC-MS Phenomenex LUNA C-18 4.6 X 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 3.89 min, 99% homogeneity index. [00260] LCMS: Anal. Calcd. for C21H21Cl2N3O4449.09 found: 450.11 (M+H)+. [00261] HRMS: Anal. Calcd. for C21H22Cl2N3O4 450.0987 found: 450.0981 (M+H)+.[00262] For 3-isomer: 1H NMR (400 MHz, CDCl3) delta 8.38 (s, 1H), 7.41 (d, J= 1.7 Hz, 1H), 7.41 (m, 2H), 3.98-4.17 (m, 2H), 2.77 (s, 3H), 1.27 (s, 9H), 1.22 (t, J= 7.0 Hz, 3H).[00263] 13C NMR (400 MHz, CDCl3) delta 164.0, 159.1, 158.3, 150.5, 144.4, 142.4, 137.0, 134.8, 131.7, 129.9, 128.9, 126.9, 121.1, 117.6, 83.9, 61.0, 27.5, 23.5, 14.3. [00264] HPLC-MS Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 3.89 min, 99% homogeneity index.[00265] LCMS: Anal. Calcd. for C21H21Cl2N3O4449.09 found: 450.20 (M+H)+. EPO [00266] The regiochemistry for the 2- and 3-isomers were unequivocally established by single crystal X-ray analysis for both compounds.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/71752; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem