Category: 1260243-04-6

These common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-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. Recommanded Product: 1260243-04-6

To a mixture of ethyl 5-amino- lH-pyrazole-4-carboxylate (150.00 g, 1.08 mmol) and ethyl (E)-3-ethoxyprop-2-enoate (292.16 g, 2.03 mol) in DMF (3.2 L) was added Cs2C03 (656.77 g, 2.02 mol) in one portion at 20 °C under N2. The mixture was stirred at 110 °C for 6 h. TLC (PE: EtOAc=l : 1) showed the reaction was completed. The mixture was cooled to 20 °C and filtered through a celite pad. The filter cake was washed with ethyl acetate (3X30 mL). The filtrate was added to H20 (2 L) and acidified with HOAc to pH=4. The resultant precipitate was filtered to afford A-1-7 (173.00 g, 834.98 mmol, 86.36percent yield) as a white solid: 1H NMR (400 MHz, DMSO-d6) delta 8.54 (d, 7=7.91 Hz, 1H), 8.12 (s, 1H), 6.13 (d, 7=7.91 Hz, 1H), 4.27 (q, 7=7.11 Hz, 2H), 1.28 (t, 7=7.09 Hz, 3H).

The synthetic route of Ethyl 5-amino-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TP THERAPEUTICS, INC.; CUI, Jingrong J.; LI, Yishan; ROGERS, Evan W.; ZHAI, Dayong; DENG, Wei; UNG, Jane; (170 pag.)WO2017/4342; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1260243-04-6, These common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-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.

Step 3: preparation of ethyl 5-acetamido-1 H-pyrazole-4-carboxylate. A mixture of ethyl 5-amino-1H-pyrazole-4-carboxylate (100 g, 0.65 mol) and acetyl chloride (441.2 g, 5.62 mol) at 0°C was heated to reflux for 4h. The reaction was concentrated in vacuo to remove excess acetyl chloride. Water (1.0 L) was added and the mixture was stirred for 16 h, after which it was filtered to afford the title compound as an off white solid (120g, 94percent). MS (M+H) m/z 198. 1H NMR (400 MHz, CDCI3) 6 ppm: 9.57(1 H, s), 7.75 (1H, s), 4.33-4.28 (2H, q, J = 7.08), 2.27 (3H, s), 1 .37-1.34 (3H, s).

The synthetic route of 1260243-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; SPRINGER, John Robert; DEVADAS, Balekudru; GARLAND, Danny James; GRAPPERHAUS, Margaret Lanahan; HAN, Seungil; HOCKERMAN, Susan Landis; HUGHES, Robert Owen; SAIAH, Eddine; SCHNUTE, Mark Edward; SELNESS, Shaun Raj; WALKER, Daniel Patrick; WAN, Zhao-Kui; XING, Li; ZAPF, Christoph Wolfgang; SCHMIDT, Michelle, Ann; WO2014/68527; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1260243-04-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1260243-04-6 name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example C.22 5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid; a. A mixture of ethyl 3-(4-chloro-phenyl)-3-oxo-propionate (18.1 g, 0.080 mol) and ethyl 5-amino-1H-pyrazole-4-carboxylate (13.7 g, 0.088 mol) was stirred at for 3 h 160° C. Ethyl acetate (40 mL) and hexane (40 mL) were successively added to the cooled mixture and stirring was continued at 0° C. for 0.5 h. The crystals were isolated by filtration and triturated for 1.2 h with 0.2 N HCl (80 mL). The solid was filtered off, washed with water and dried to give ethyl 5-(4-chloro-phenyl)-7-hydroxy-pyrazolo[1,5-a]pyrimidine-3-carboxylate (13.3 g, 52percent). White solid. MS (ISN) 316.3 [(M-H)-]; mp 190-192° C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-amino-1H-pyrazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; McArthur, Silvia Gatti; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2007/72879; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, belongs to pyrazoles-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 1260243-04-6, category: pyrazoles-derivatives

Cs2CO3 (64.20 g, 197.20 mmol) was added to a solution of ethyl 5-amino-1H-pyrazole- 4-carboxylate (20.40 g, 131.40 mmol) and ethyl-3-ethoxyacrylate (28.6 mL, 197.20 mmol) in DMF (250 mL). The reaction mixture was stirred at 110 C for 16 h. The mixture was cooled to room temp and the pH was adjusted to 4 by the addition of AcOH (80 mL). The mixture was concentrated in vacuo and the residue partitioned between CH2Cl2 H2O (1000 mL, 1:1). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3 X 500 mL). The combined organics were washed with brine, dried (MgS04) and concentrated. The crude residue was suspended in EtOH (300 mL) and heated to boiling. After cooling to room temperature the solid was collected by filtration, rinsed with EtOH, then Et20 and dried under vacuum to give ethyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate (25.16 g, 92 %). MS (ESI) calcd for C9H9N3O3 (m/z): 207.06; found: 208 [M+H]

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; WO2013/59587; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, belongs to pyrazoles-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 1260243-04-6, Computed Properties of C6H9N3O2

Example C.22 5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid; a. A mixture of ethyl 3-(4-chloro-phenyl)-3-oxo-propionate (18.1 g, 0.080 mol) and ethyl 5-amino-1H-pyrazole-4-carboxylate (13.7 g, 0.088 mol) was stirred at for 3 h 160 C. Ethyl acetate (40 mL) and hexane (40 mL) were successively added to the cooled mixture and stirring was continued at 0 C. for 0.5 h. The crystals were isolated by filtration and triturated for 1.2 h with 0.2 N HCl (80 mL). The solid was filtered off, washed with water and dried to give ethyl 5-(4-chloro-phenyl)-7-hydroxy-pyrazolo[1,5-a]pyrimidine-3-carboxylate (13.3 g, 52%). White solid. MS (ISN) 316.3 [(M-H)-]; mp 190-192 C.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; McArthur, Silvia Gatti; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2007/72879; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1260243-04-6,Some common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, molecular formula is C6H9N3O2, 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 solution of ethyl 5-amino-lH-pyrazole-4-carboxylate (13.7 g, 88.0 mmol) in DMF (150 mL) was added ethyl (//)-3 -ethoxy aery late (15.2 g, 106.0 mmol) and the reaction mixture was stirred at 1 l0C for 1 h. The reaction mixture was diluted with water, adjusted pH to 2 with 2 N HC1 aqueous. The mixture was filtrated and the residue was washed with water and ethyl acetate and the filtrate was concentrated under reduced pressure to give the title compound as a white solid (18.3 g, 100 %), which used in next step without further purification. ‘H NMR (400 MHz, CDCb): d, 1.28 (t, J= 6.8Hz, 3H), 4.27 (q, J= 12 Hz, 2H), 6.15 (d, J= 7.6 Hz, 1H), 8.13 (s, 1H), 8.57 (d, J= 8.0 Hz, 1H), 11.74 (brs, 1H). ESI-MS (EI+, m/z): 208.1.

The synthetic route of 1260243-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; HATCHER, John M.; POWELL, Chelsea E.; JANNE, Pasi A.; (439 pag.)WO2020/69106; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – 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. 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Safety of Ethyl 5-amino-1H-pyrazole-4-carboxylate

A mixture of ethyl 5-methyl-7,8-dihydro-6H-cyclopenta[e]pyrazolo[1 ,5-a]pyrim idine-3-carboxylate (major isomer) and ethyl 8-methyl-6, 7-dihydro-5H-cyclopenta[d]pyrazolo[1 ?5-a]pyrimidine-3-carboxylate (minor isomer) (1 .28 g, 5.22 mmol, ratio of isomers ca 85/15) was stirred in a mixture of lithium hydroxide (26 ml, 26 mmol, 1 M aqueous solution), tetrahydrofuran (43 ml) and methanol (9.1 ml) for 3 days at room temperature. For work-up, aqueous hydrochloric acid (2 M) was added and the precipitate formed was collected byfiltration, washed with water and dried to yield the title compounds as mixture of isomers (ca10:1) (770 mg, 68percent).Maior isomer:[C-MS (Method 1): R = 0.71 mm; MS (ESIpos) m/z = 218.1 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 12.83-11.51 (br. s, 1H), 8.48 (5, 1H), 3.03 (t, 2H),2.55 (5, 3H), 2.30-2.21 (m, 2H).Minor isomer (characteristic sicinals ciiven):1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 8.45 (5, 1H), 3.00-2.95 (m, 2H), 2.68 (5, 3H), 2.20-2.10 (m, 2H). (benzotriazol-1 -yloxy)tripyrrolidinophosphonium hexafluorophosphate (172 mg, 0.331 mmol)was added to a mixture of 5-methyl-7,8-dihydro-6H-cyclopenta[e]pyrazolo[1 ,5-a]pyrim idine-3-carboxylic acid (major isomer) and 8-methyl-6, 7-dihydro-5H-cyclopenta[d]pyrazolo[1 ?5- a]pyrimidine-3-carboxylic acid (minor isomer) (60.0 mg, 0.276 mmol, ratio of isomers: 10/1), trans-4-am ino-N-(2-chloro-4-f luorophenyl)cyclohexanecarboxam ide hydrochloride (76.4 mg, 0.249 mmol) and 192 hI (1.11 mmol) N-ethyl-N-isopropylpropan-2-amine in 2.0 ml N,N10 dimethylformamide and the mixture was stirred over night at room temperature. For work-up,water was added and the precipitate was collected by filtration, washed with water and dried under vacuum at 500 to provide the title compound (103 mg) together with its isomer N{trans-4-[(2-chloro-4-fluorophenyl)carbamoyl]cyclohexyl}-8-methyl-6,7-dihydro-5H-cyclopenta[d]pyrazolo[1 ,5-a]pyrimidine-3-carboxamide (ratios of isomers ca. 10/1 by 1 HNMR). The two isomers were separated by preparative HPLC [Instrument: Labomatic PumpeHD-5000, Labomatic SP-3000, Labocord 5000, Labomatic Labcol Vario 4000, Gilson GX241; Colum: Chiralpak IE Slim 250×30 mm Nr.027; Solvent: ethanol / methanol / diethylamine 50:50:0.1 (v/v/v), flow: 30 mI/mm; temperature: room temperature; MWD 254 nm] to give N-{trans-4-[(2-chloro-4-fluorophenyl)carbamoyl]cyclohexyl}-5-methyl-7,8-dihydro-6H-cyclopenta[e]pyrazolo[1 ,5-a]pyrimidine-3-carboxamide (76.0 mg, 57percent yield). The minor isomer was not isolated in pure form.LC-MS (Method 2): R = 1 .23 mm; MS (ESIpos) m/z = 470.1 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 9.51 (br. s, 1H), 8.47 (5, 1H), 8.05 (d, 1H), 7.62(dd, 1H), 7.51 (dd, 1H), 7.23 (td, 1H), 3.87-3.72 (m, 1H), 3.40-3.36 (m, 2H), 3.07-3.01 (m,2H), 2.60 (5, 3H), 2.32-2.22 (m, 2H), 2.15-2.06 (m, 2H), 2.02-1.93 (m, 2H), 1.68-1.50 (m,2H), 1.47-1.32 (m, 2H).

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; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – 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. 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Formula: C6H9N3O2

General procedure: A mixture of ethyl-5-amino-1H-pyrazole-4-carboxylate 1 (1.0 mmol), an appropriate aldehyde 2 (1.0 mmol) and aterminal alkyne 3 (1.0 mmol) in acetic acid (5 mL) was stirred at 25 C for 10 min. The mixture was then stirred at 60 C under ultrasound using a laboratory ultrasonic bath SONOREX SUPER RK 510H model producing irradiationof 35 kHz for 30 min in the presence of air. The increase of bath temperature beyond 60 C due to the prolonged ultrasound irradiation was controlled by adding cold water time to time. After completion of the reaction the mixture was cooled to room temperature, poured into ethyl acetate (25 mL) and washed with brine solution (2 x 15 mL) followed by 10% NaHCO3 solution (2 x 15 mL). The organiclayer was collected, dried over anhydrous Na2SO4, filteredand concentrated under low vacuum. The residue isolatedwas purified by column chromatography over silica gel using3-8% petroleum ether-EtOAc to give the desired product.

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:
Article; Suresha, Namburi; Durgaraoa, Bodapati Veera; Ratnakar; Kolli, Sunder Kumar; Ashfaq, Mohd Ashraf; Rao, Mandava V. Basaveswara; Pal, Manojit; Letters in drug design and discovery; vol. 14; 10; (2017); p. 1176 – 1183;,
Pyrazole – Wikipedia,
Pyrazoles – 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. 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

General procedure: A mixture of ethyl-5-amino-1H-pyrazole-4-carboxylate 1 (1.0 mmol), an appropriate aldehyde 2 (1.0 mmol) and aterminal alkyne 3 (1.0 mmol) in acetic acid (5 mL) was stirred at 25 °C for 10 min. The mixture was then stirred at 60 °C under ultrasound using a laboratory ultrasonic bath SONOREX SUPER RK 510H model producing irradiationof 35 kHz for 30 min in the presence of air. The increase of bath temperature beyond 60 °C due to the prolonged ultrasound irradiation was controlled by adding cold water time to time. After completion of the reaction the mixture was cooled to room temperature, poured into ethyl acetate (25 mL) and washed with brine solution (2 x 15 mL) followed by 10percent NaHCO3 solution (2 x 15 mL). The organiclayer was collected, dried over anhydrous Na2SO4, filteredand concentrated under low vacuum. The residue isolatedwas purified by column chromatography over silica gel using3-8percent petroleum ether-EtOAc to give the desired product.

The synthetic route of 1260243-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Suresha, Namburi; Durgaraoa, Bodapati Veera; Ratnakar; Kolli, Sunder Kumar; Ashfaq, Mohd Ashraf; Rao, Mandava V. Basaveswara; Pal, Manojit; Letters in drug design and discovery; vol. 14; 10; (2017); p. 1176 – 1183;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1260243-04-6,Some common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, molecular formula is C6H9N3O2, 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.

General procedure: A mixture of ethyl-5-amino-1H-pyrazole-4-carboxylate 1 (1.0 mmol), an appropriate aldehyde 2 (1.0 mmol) and aterminal alkyne 3 (1.0 mmol) in acetic acid (5 mL) was stirred at 25 °C for 10 min. The mixture was then stirred at 60 °C under ultrasound using a laboratory ultrasonic bath SONOREX SUPER RK 510H model producing irradiationof 35 kHz for 30 min in the presence of air. The increase of bath temperature beyond 60 °C due to the prolonged ultrasound irradiation was controlled by adding cold water time to time. After completion of the reaction the mixture was cooled to room temperature, poured into ethyl acetate (25 mL) and washed with brine solution (2 x 15 mL) followed by 10percent NaHCO3 solution (2 x 15 mL). The organiclayer was collected, dried over anhydrous Na2SO4, filteredand concentrated under low vacuum. The residue isolatedwas purified by column chromatography over silica gel using3-8percent petroleum ether-EtOAc to give the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 5-amino-1H-pyrazole-4-carboxylate, its application will become more common.

Reference:
Article; Suresha, Namburi; Durgaraoa, Bodapati Veera; Ratnakar; Kolli, Sunder Kumar; Ashfaq, Mohd Ashraf; Rao, Mandava V. Basaveswara; Pal, Manojit; Letters in drug design and discovery; vol. 14; 10; (2017); p. 1176 – 1183;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics