Category: 816-27-3

Synthetic Route 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,
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Related Products 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

Reference of 816-27-3, These common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, 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.

a) 5-Benzyl-1H-[1,2,4]triazole-3-carboxylic acid butyl ester Ethyl-2-ethoxy-2-iminoacetate (1.318 g, 9.08 mmol) and phenyl acetic acid hydrazide (1.364 g, 9.08 mmol) were mixed together in ethanol (20 ml) and stirred at 80 C. for 1 h. Ethanol was evaporated. The residue was dissolved in n-butanol (20 ml). The reaction mixture was stirred at 150 C. for 20 h, then solvents were evaporated. The residue was suspended in acetonitrile and the precipitate was filtered off. The filtrate was purified by prep. HPLC (column: Interchrom C18 ODB, 10 um, 250*28 mm, 23 C.; A: water+0.1% HCOOH, B: ORG+0.1% HCOOH [ORG=methanol/acetonitrile 4:1]; gradient 20% B 2.5 min, 20-100% B in 35 min, 100% B for 2.5 min) to give the title compound. UPLC-MS (method F) Rt=0.85 min, [M+H]+=260.3; HPLC (method G) Rt=1.861 min.

Statistics shows that Ethyl 2-ethoxy-2-iminoacetate is playing an increasingly important role. we look forward to future research findings about 816-27-3.

Reference:
Patent; NOVARTIS AG; US2012/35168; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 816-27-3, 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.

A mixture of 4-chloropyridine-3-sulfonamide (500 mg, 2.6 mmol), ethyl 2-ethoxy-2- iminoacetate (565 mg, 3.9 mmol) and DBU (790 mg, 5.2 mmol) in ethanol (10 mL) was heated in a sealed tube at 150 C for 0.5 h then cooled to r.t.. The mixture was diluted with water (5 mL), adjusted to pH 5 with 1 M aqueous HCI and exacted with DCM (10 mL x 3). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by preparative TLC (MeOH/DCM = 1 :20, v/v) to give the product as a yellow solid (100 mg, 15% yield). LCMS (ES-API) Rt 0.47 min; m/z 256 [M+H]+. 1H NMR (400 MHz, d6-DMSO), 9.05 (s, 1H), 8.76 (d, J = 5.6 Hz, 1H), 7.64 (d, J = 5.6 Hz, 1H), 4.40 (q, J = 7.2 Hz, 2H), 1.37 (t, J = 7.2 Hz, 3H).

The synthetic route of Ethyl 2-ethoxy-2-iminoacetate has been constantly updated, and we look forward to future research findings.

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

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. COA of Formula: C6H11NO3

(3) A mixture of ethyl 2-imino-2-ethoxyacetate (60 g) (purity 78.8%) and ammonium chloride (17.4 g) in methanol (180ml) was stirred for 3 hours at room temperature and cooled to -15 to -10 C. To the resulting mixture containing 1-methoxycarbonyl formamidine hydrochloride were dropwise added bromine (51.2 g) over a period of 10 minutes, triethylamine (71.1 g) over a period of 30 minutes and a solution of potassium thiocyanate (31.0 g) in methanol (150 ml) over a period of 30 minutes. The resulting mixture was stirred at -10 to -5 C. for 15 minutes and at 0 to 5 C. for an additional 1.5 hours. Precipitates were collected by filtration, washed with methanol and thereto was added cold water (200 ml). The mixture was stirred and the precipitates were collected by filtration, washed with cold water and dried to give methyl 5-amino-1,2,4-thiadiazole-3-carboxylate (32.5 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 816-27-3, its application will become more common.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4425340; (1984); A;,
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., Recommanded Product: Ethyl 2-ethoxy-2-iminoacetate

A mixture of 2-chloropyridine-3-sulfonamide (115) (50 mg, 0.26 mmol), ethyl 2-ethoxy-2- iminoacetate (56 mg, 0.39 mmol) and DBU (79 mg, 0.52 mmol) in ethanol (5 mL) was heated in a sealed tube at 130 C for 0.5 h then cooled to r.t.. The mixture was diluted with water (5 mL), adjusted to pH 5 with 1 M aqueous HCI and extracted with DCM (10 mL x 3). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by preparative TLC (MeOH/DCM = 1 :20) to give the product as a yellow solid (10 mg, 15% yield). LCMS (ES-API) Rt 0.51 min; m/z 256.1 [M+H]+. 1H NMR (400 MHz, d6-DMSO) 8.81 (dd, J = 4.8, 2.0 Hz, 1H), 8.43 (dd, J = 8.0, 1.6 Hz, 1H), 7.63 (dd, J = 8.0, 4.8 Hz, 1H), 4.41 (q, J = 7.2 Hz, 2H), 1.37 (t, J = 7.2 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; 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

Synthetic Route of 816-27-3, These common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, 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.

A mixture of cis-l-amino-4-((tert-butyldimethylsilyl)oxy)-5-phenylpyrrolidin-2-one (9.0 g, 29.4 mmol) and ethyl 2-ethoxy-2-imino-acetate (21.3 g, 146.8 mmol) in toluene (500 mL) was heated at 90 C for 18 h and concentrated under reduced pressure. The residue was diluted with water (200 mL) and extracted with ethyl acetate (3 x 150 mL). The combined organic layers were concentrated under reduce pressure to afford crude ethyl cis-2-((3-((tert-butyldimethylsilyl)oxy) -5-oxo-2- phenylpyrrolidin-l-yl)amino)-2-iminoacetate (10.0 g, 84%) as a brown oil. LC-MS RT= 1.128 min, m/z = 406.4 [M + H]+. LCMS (10 to 80% acetonitrile in water + 0.03% trifluoacetic acid over 2.0 in, ESI+ found [M+H] = 406.4.

Statistics shows that Ethyl 2-ethoxy-2-iminoacetate is playing an increasingly important role. we look forward to future research findings about 816-27-3.

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, name: Ethyl 2-ethoxy-2-iminoacetate

To a solution of cis-1-amino-3-[tert-butyl(dimethyl)silyl]oxy-5-phenyl-pyrrolidin-2-one (9.5 g, 31.0 mmol) in ethanol (250 mL) was added ethyl 2-ethoxy-2-imino-acetate (6.7 g, 46.5 mmol). The reaction mixture was stirred at 60 C. for 6 h and subsequently concentrated under reduced pressure to afford crude ethyl 2-[[cis-3-[tert-butyl(dimethyl)silyl]oxy-2-oxo-5-phenyl-pyrrolidin-1-yl]amino]-2-imino-acetate as a yellow oil (10.6 g, 84%), used in the next step without further purification. LCMS RT=2.106 min, m/z=406.2 [M+H]-. LCMS (10 to 80% acetonitrile in water+0.1% ammonia water over 3.0 mins) retention time 2.106 mm, ESI+ found [M+H]=406.2.

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

Reference of 816-27-3, 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.

To a suspension of 3-methoxy-benzene-1,2-diamine sulfate, Example 25(b), (2.36 g, 10 mmol) in EtOH (15 mL) and H2O (1 mL) was added NaHCO3 (1.68 g, 20 mmol, J T Baker). When gas evolution was complete, ethoxy-imino-acetic acid ethyl ester (1.6 g, 11 mmol, prepared according to J. Chem. Soc. Perkin. Trans. 1, 1999, 1789) was added and the mixture was stirred at room temperature for 16 h. The reaction was diluted with sat. aq. NaHCO3 and extracted with 25% i-PrOH(CHCl3 (5¡Á). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (gradient: 0-5% MeOH/CH2Cl2) afforded 3-amino-8-methoxy-1H-quinoxalin-2-one as a light-brown powder [MS (ESI, pos. ion) m/z: 192 (M+1)] and 3-amino-5-methoxy-1H-quinoxalin-2-one as a light-brown powder [MS (ESI, pos. ion) m/z: 192 (M+1)].

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; Wang, Hui-Ling; Balan, Chenera; Doherty, Elizabeth M.; Falsey, James R.; Gore, Vijay Keshav; Katon, Jodie; Norman, Mark H.; US2005/176726; (2005); 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.

2-(3-Fluorophenyl)acetohydrazide (2.90 g, 17.22 mmol) and ethyl 2-ethoxy-2- iminoacetate (2.5 g, 17.22 mmol) in ethanol (30 mL) was stirred under nitrogen at rt overnight. The resultant suspension was filtered. The white solid was washed with EtOH and dried under vacuum to give the title compound ethyl 2-amino-2-(2-(2-(3- fluorophenyl)acetyl)hydrazono)acetate (3 g, 11.23 mmol, 65.2 % yield), which was used without further purification. MS (m/z) 268 (M+H+).

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; JEONG, Jae U.; KANG, Jianxing; LEISTER, Lara Kathryn; ROMANO, Joseph J.; (82 pag.)WO2018/7973; (2018); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics