Category: 816-27-3

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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H11NO3

To a solution of cyclopropanecarbohydrazide (6.9 g, 69 mmol, 1 equiv) in ethanol (20mL) was added ethyl 2-ethoxy-2-iminoacetate (10 g, 69 mmol, 1 equiv). The mixture was stirred at 40C overnight. The resulting solid was filtered and the filter cake was washed with cool ethanol to afford ethyl 2-(2-(cyclopropanecarbonyl)hydrazinyl)-2- iminoacetate as a white solid, which was used for next step without further purification(5.8 g, 42.7% yield). LC-MS: m/z 200.1 (M+H) +

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 816-27-3.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 816-27-3,Some common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, molecular formula is C6H11NO3, 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.

A mixture of (3-chloro-quinolin-6-yl)-acetic acid hydrazide (4.0 g, 16.97 mmol, 1.0 eq) and ethoxy-imino-acetic acid ethyl ester (4.9 g, 33.95 mmol, 2.0 eq) in EtOH (200 mL) and AcOH (10 mL) was stirred at rt for 30 min, and then concentrated. The resulting residue was dried in vacuo to afford amino-{[2-(3-chloro-quinolin-6-yl)-acetyl]-hydrazono}-acetic acid ethyl ester (5.0 g, 89%) as a white solid.

The synthetic route of 816-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (183 pag.)WO2019/142053; (2019); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 816-27-3,Some common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, molecular formula is C6H11NO3, 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.

Sodium hydride (60% in oil, 0.390 g, 9.7 mmol) was added to a solution of 3-[tert- butyl(dimethyl)silyl]oxy-5-(3-fluoro-2-pyridyl)pyrrolidin-2-one (2.0 g, 6.4 mmol) in N,N- dimethylformamide (64 mL) at 0C. After 30 min, O-diphenylphosphorylhydroxylamine (2.3 g, 9.7 mmol) was added. The reaction was warmed to rt and stirred for 16h. The reaction was filtered and the filtrate was evaporated under reduced pressure. The crude residue was submitted to the next reaction without further purification. LCMS RT = 1.34 min, m/z = 326.0 [M + H]+ and LCMS RT = 1.30 min, m/z = 326.0 [M + H]+. Ethyl 2-ethoxy-2-iminoacetate (2.50 g, 16 mmol) and the crude residue were dissolved in ethanol (23 mL) and the reaction was heated at 90C for 16h. After cooling to rt, the reaction was filtered and the filtrate was concentrated under reduced pressure. The crude residue was submitted to the next reaction without further purification. LCMS RT = 1.38 min, m/z = 425.0 [M + H]+ and LCMS RT = 1.34 min, m/z = 425.0 [M + H]+. p-Toluenesulfonic acid monohydrate (1.5 g, 7.7 mmol) was added to a solution of the crude residue in toluene (25 mL). The reaction was heated at 120C for 16 h. After cooling to rt the reaction was filtered and the filtrate was concentrated under reduced pressure. The crude residue was submitted to the next reaction without further purification. LCMS RT = 1.55 min, m/z = 407.0 [M + H]+ and LCMS RT = 1.50 min, m/z = 407.1 [M + H]+. Tetrabutylammonium fluoride (1.0 M in THF, 6.4 mL, 6.4 mmol) was added to a solution of the crude residue in THF (21 mL) and the reaction was heated at 40C for 1 h. After cooling to rt saturated aqueous ammonium chloride was added. The aqueous layer was extracted with isopropyl acetate (4 x 50 mL). The combined organic layers were dried over sodium sulfate, concentrated and the crude residue was purified by flash column chromatography (silica 0% to 10% methanol/ dichloromethane) to give ethyl 5-(3-fluoro-2-pyridyl)-7-hydroxy-6,7-dihydro-5H- pyrrolo[l ,2-b] [l ,2,4]triazole-2-carboxylate (0.800 g, 2.74 mmol, 42% yield). NMR (400 MHz, Chloroform-if) 1 : 1 mixture of diastereomers delta 8.41 – 8.29 (m, 1H), 7.63 – 7.26 (m, 2H), 6.12 (dd, J = 8.1 , 4.4 Hz, 0.5H), 6.07 (d, J = 8.2 Hz, 0.5H), 5.64 (dd, J = 7.6, 4.0 Hz, 0.5H), 5.21 (d, J = 6.5 Hz, 0.5H), 4.51 – 4.38 (m, 2H), 3.45 (ddd, J = 14.7, 8.3, 6.6 Hz, 0.5H), 3.29 (ddd, J = 13.8, 7.5, 4.3 Hz, 0.5H), 3.10 (ddd, J = 13.8, 8.1 , 4.0 Hz, 0.5H), 2.74 (d, J = 14.4 Hz, 0.5H), 1.40 (t, J = 7.1 Hz, 3H). LCMS RT = 0.89 min, m/z = 292.9 [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 Ethyl 2-ethoxy-2-iminoacetate, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, belongs to esters-buliding-blocks 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 816-27-3, category: esters-buliding-blocks

To 2-phenylacetohydrazide (39.5 g, 263 mmol) in ethanol (150 mL) was added ethyl 2- ethoxy-2-iminoacetate (39.5 g, 272 mmol) and diethyl ether (200 mL). The reaction mixture was stirred for 10 min and solid formed. The reaction mixture was stirred for 5 hours and diethyl ether (50 mL) was added. The resulting mixture was stirred for 17 hours The solid was filtered, rinsed with diethyl ether, and dried to give ethyl 2-amino-2-(2-(2- phenylacetyl)hydrazono)acetate as a white solid (59 g, 85 % yield). The filtrate sat for 5 days and additional white solid precipitated out. The solid was filtered and dried to give 2-amino-2-(2-(2-phenylacetyl)hydrazono)acetate as a white solid (4.8 g) (92% total yield). MS ES+ m/z 250.1 [M+H]+; NMR (400 MHz, DMSO-d6) delta 9.95 (d, J=17.18 Hz, 1H), 7.13-7.37 (m, 5H), 6.50 (d, 2H), 4.24 (dq, J=7.07, 10.86 Hz, 2H), 3.86 (s, 1H), 3.50 (s, 1H), 1.27 (dt, J=7.07, 17.43 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-ethoxy-2-iminoacetate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANBARI, Jill Marinis; BERTIN, John J.; JEONG, Jae U.; (139 pag.)WO2018/154520; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 816-27-3, 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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-aminopyridine-4-sulfonamide (112) (500 mg, 2.89 mmol), ethyl 2-ethoxy-2- iminoacetate (629 mg, 4.34 mmol) and DBU (879 mg, 5.78 mmol) in EtOH (10 mL) was heated in a microwave at 135 C for 30 min then allowed to cool to r.t.. The mixture was concentrated and the residue was dissolved in water, acidified to pH 2 with 1 M aqueous HCI and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04, filtered, concentrated and the residue was purified by preparative TLC (MeOH/DCM = 1 :20) to give the product (50 mg, 7% yield) as a yellow solid. LCMS (ES- API): Rt 0.51 min; m/z 255.9 [M+H] +. 1 H NMR (400 MHz, d6-DMSO) delta 13.2 (brs, 1H), 9.09 (s, 1H), 8.81 (d, J = 5.2 Hz, 1H), 7.88 (d, J =5.2 Hz, 1H), 4.42 (t, J = 7.2 Hz, 2H), 1.37 (t, J = 7.2 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-ethoxy-2-iminoacetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin Joseph; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; LAGIAKOS, Helen Rachel; WALKER, Scott Raymond; BOZIKIS, Ylva Elisabet Bergman; STEVENSON, Graeme Irvine; CUZZUPE, Anthony Nicholas; STUPPLE, Paul Anthony; (313 pag.)WO2019/43139; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, belongs to esters-buliding-blocks 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 816-27-3, Product Details of 816-27-3

2-(3-Chloroquinolin-6-yl)acetohydrazide (170.0 mg, 0.723 mmol, 1.0 eq) and ethyl 2-ethoxy-2-iminoacetate (231.0 mg, 1.591 mmol, 2.0 eq) in ethanol (20.0 mL) were stirred at 30 C for 72.0 h. The solvent was removed in vacuo, to provide (Z)-ethyl 2-amino- 2-(2-(2-(3-chloroquinolin-6-yl)acetyl)hydrazono)acetate (242.0 mg, ca. 100%).

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-ethoxy-2-iminoacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, A new synthetic method of this compound is introduced below., SDS of cas: 816-27-3

2-(2-fluorophenyl)acetohydrazide (7.05 g, 41.9 mmol) was partially dissolved in ethanol (30 mL), and then ethyl 2-ethoxy-2-iminoacetate (6.39 g, 44.0 mmol) and diethyl ether (35 mL) were added. The reaction mixture was stirred for 0.5 hours, and diethyl ether (100 mL) was added. The resulting mixture was stirred for 18 hours. The solid was filtered off, rinsed with diethyl ether, and dried to give ethyl 2-amino-2-(2-(2-(2- fluorophenyl)acetyl)hydrazono)acetate as an off-white solid (10 g, 89% yield). MS ES+ m/z 26% [M+H]+; NMR (400 MHz, DMSO-de) delta 9.80-10.25 (m, 1H), 7.25-7.43 (m, 2H), 7.09-7.21 (m, 2H), 6.42-6.60 (m, 2H), 4.23 (dq, J=1.52, 7.07 Hz, 2H), 3.92 (s, 1H), 3.58 (s, 1H), 1.26 (dt, J=5.05, 7.07 Hz, 3H).

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANBARI, Jill Marinis; BERTIN, John J.; JEONG, Jae U.; (139 pag.)WO2018/154520; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H11NO3

A mixture of l -amino-3-[tert-butyl (dimethyl) silyl] oxy-5-cyclopropyl-pyrrolidin-2-one (10.5 g, 38.83 mmol) and ethyl 2-ethoxy-2-imino-acetate (14.1 g, 97.06 mmol) in ethanol (150 mL) was stirred at 90 C for 12 h and concentrated under reduced pressure to afford crude ethyl 2-[[3-[tert- butyl (dimethyl) silyl] oxy-5-cyclopropyl-2-oxo-pyrrolidin-l-yl] amino]-2-imino-acetate (10.0 g, 70%) as a yellow oil. LCMS RT = 0.804 min, m/z =370.2 [M + H]+. LCMS (5 to 95% acetonitrile in water + 0.03%o trifluoacetic acid over 1.5 mins) retention time 0.804 min, ESI+ found [M+H] =370.2.

The synthetic route of 816-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 816-27-3 as follows. SDS of cas: 816-27-3

To a solution of 1-amino-5-(1,1-difluoropropyl)pyrrolidin-2-one (120 mg, 0.67 mmol) in ethanol (5 mL) was added ethyl 2-ethoxy-2-imino-acetate (489 mg, 3.37 mmol). The reaction mixture was stirred at 60 C. for 16 h and subsequently concentrated under reduced pressure to afford ethyl 2-[[2-(1,1-difluoropropyl)-5-oxo-pyrrolidin-1-yl]amino]-2-imino-acetate (600 mg, 80%, 40% purity) as a yellow oil, used as is in the next step.

According to the analysis of related databases, 816-27-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Patel, Snahel; Hamilton, Gregory; (73 pag.)US2018/170927; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 2-ethoxy-2-iminoacetate

To a solution of cyclopropanecarbohydrazide (6.9 g, 69 mmol, 1 equiv) in ethanol (20mL) was added ethyl 2-ethoxy-2-iminoacetate (10 g, 69 mmol, 1 equiv). The mixture was stirred at 40C overnight. The resulting solid was filtered and the filter cake was washed with cool ethanol to afford ethyl 2-(2-(cyclopropanecarbonyl)hydrazinyl)-2- iminoacetate as a white solid, which was used for next step without further purification(5.8 g, 42.7% yield). LC-MS: m/z 200.1 (M+H) +

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 816-27-3.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics