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9/1/2021 News Introduction of a new synthetic route about 1280210-79-8

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, and friends who are interested can also refer to it.

Electric Literature of 1280210-79-8, 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. 1280210-79-8 name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-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.

To a solution of tert-butyl 4,6-dihydropyrrolo[3,4- c]pyrazole-5(2H)-carboxylate (15.0 g, 71.8 mmol) in DMF (150 mL) was added NaH (60% in mineral oil) (8.6 g, 215.4 mmol) while the reaction mixture was cooled with an ice bath. When the addition was complete, the resulting mixture was allowed to warm to room temperature and was stirred at room temperature for 30 min. At this point, l-bromo-2- methoxyethane (19.8 g, 143.6 mmol) was added into the reaction mixture, and stirring was continued at room temperature for 2 h. The reaction mixture was then quenched with water (300 mL), and extracted with EtOAc (150 mL x 3). The combined organic layer was washed with brine (100 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM : MeOH = 100 : 1 ~ 30 : 1) to give a mixture of 122 and 122-A (19.0 g, 99%) as a colorless oil. MS 268.2 [M + H]+. [0072] Synthesis of 123 and 123-A. To a solution of 122 and 122-A (6.5 g, 24.3 mmol) in DCM (60 mL) cooled with an ice bath was added TFA (30 mL). The reaction mixture was stirred at room temperature for 1 h, whereupon the solvent was removed in vacuo to give 123 and 123-A as a crude product mixture which was used directly in the next step without further purification. MS 168.1 [M+H]+.

Reference:
Patent; RODIN THERAPEUTICS, INC; FULLER, Nathan, Oliver; LOWE, John, A.; (45 pag.)WO2019/32528; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

The origin of a common compound about tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, its application will become more common.

Application of 1280210-79-8,Some common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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 stirred solution of /erf-butyl 2,6^hydropyrrolo[3,4-c]pyrazole-5(4 /)- carboxylate (20 g, 96 mmol) in DMF (200 mL) at 0 C was added sodium hydride (4.21 g, 105 mmol). After stirring for 1 h at RT, 2-trimetbylsilylethoxymethyl chloride (SEM-C1) (4.65 mL, 26.3 mmol) was added. The resulting mixture was stirred at RT overnight. The mixture was quenched with saturated NuEta4OmicronEta, and the solvents were removed. The residue was diluted with ethyl acetate (500 mL), washed with water, brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on a silica gel Biotage 65i column, eluting with 0 to 20% ethyl acetate in hexanes to give the title compound as a colorless gum. LC-MS: 340.1 (Mu+Eta)

Reference:
Patent; MERCK SHARP & DOHME CORP.; HICKS, Jacqueline, D.; BIFTU, Tesfaye; CHEN, Ping; QIAN, Xiaoxia; WILKENING, Robert, R.; WO2011/146358; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Extracurricular laboratory: Synthetic route of 1280210-79-8

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 1280210-79-8.

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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate

2D (3.5 g, 16.7 mmol) was dissolved in tetrahydrofuran (35 mL)Cooled to 0 C,60% sodium hydride (1.0 g, 25.4 mmol) was added,After reaction for 30 minutes, methylsulfonyl chloride (2.9 g, 25.4 mmol) was added and reacted for 1 hour.The reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (50 mL x 2). The organic layers were combined and the organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (petroleum ether / Ethyl acetate (v / v) = 1: 1) to give 2E as a white solid (2.1 g, yield 44%).

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO., LTD; ZHANG, CHEN; FAN, JIANG; LEI, MING; WEI, YONG-GANG; (61 pag.)TW2017/8223; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Simple exploration of C10H15N3O2

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

Electric Literature of 1280210-79-8, A common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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.

Under N2 protection and a condition free of water and oxygen, Intermediate 2 (604 mg, 2.87 mmol) wasdissolved in tetrahydrofuran (20 ml), which was cooled to 0C, and sodium hydride (180 mg, 60 wt%, 4.5 mmol) wasadded, followed by stirring for 30 min. Cyclopropylsulfonyl chloride (1.27 g, 9.0 mmol) was added dropwise, and thetemperature was allowed to rise spontaneously to room temperature, followed by reaction for 1 hour. The reaction was quenched by addition of water (20 ml) to the reaction solution, which was then extracted with ethyl acetate (20 ml32).The organic phases were combined, dried over anhydrous sodium sulfate, concentrated, re-dissolved in 5 ml tetrahydrofuran,and cooled to -10C to 0C. Potassium t-butoxide (36 mg, 0.32 mmol) was added, and the reaction was allowedto proceed for 28 hours at this temperature. After the reaction was completed, an aqueous solution of citric acid (1 ml,15%) was added, and water (10 ml) was added. The solution was extracted with ethyl acetate (20 mL33). The organicphases were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gelcolumn chromatography (petroleum ether/ethyl acetate (v/v) = 2:1) to obtain a white solid 1a (660 mg, yield 73%).

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Haisco Pharmaceutical Co., Ltd.; ZHANG, Chen; WANG, Jianmin; LI, Caihu; WEI, Yonggang; (64 pag.)EP3159344; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Analyzing the synthesis route of 1280210-79-8

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.

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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C10H15N3O2

4,6-Dihydro-2H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester(0.30 g, 1.43 mmol) was dissolved in tetrahydrofuran (10 mL).Nitrogen protection, sodium hydride (0.11 g, 2.85 mmol, 60%) was added at 0 C.Slowly rise to room temperature for 1 hour, then cool to 0 C,Add 5-methylthiophene-2-sulfonyl chloride (0.39 g, 1.99 mmol),The reaction was carried out for 6 hours at room temperature. The reaction was quenched by adding water (10 mL) at 0 C.Extracted with ethyl acetate (20 mL×3).The combined organic phases were washed with a saturated sodium chloride solution (10 mL) and dried over anhydrous sodium sulfate, concentrated by suction filtration, and the residue was subjected to silica gel column chromatography[ethyl acetate / petroleum ether (v / v) = 1 / 9] purified,The title compound was obtained (0.40 g, yield 76%).It is a white solid.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ruyuan Yong Xing Technology Services Co., Ltd.; Li Jianhao; Gu Zheng; Deng Xinshan; Tang Wanjun; Zhang Zongyuan; Kang Panpan; Yuan Weihui; Peng Fei; (49 pag.)CN109942583; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Research on new synthetic routes about 1280210-79-8

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

Application of 1280210-79-8, A common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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.

To a stirred solution of feri-butyl 2,6-dihydropyriOlo[3,4-c]pyrazole-5(4H)- carboxylate (Step A of Intermediate 7) (35 g, 167 mmol) in DMF (500 mL) at 0 C under N2 was added sodium hexamethyldisilazide in THF (351 mL, 351 mmol) and the mixture was stirred at 0 C for 30 min. Isobutylene oxide (74.3 mL, 836 mmol) was then slowly added. The solution was stirred at 0C for 0.5 h and then stirred at room temperature for 1 h. The solution was heated to 80C for 100 min in a microwave oven, cooled to room temperature and evapoarted under vacuum. The residue was purified by column chromatography on silica gel, eluting with a gradient of 0% to 6% CH2Cl2 MeOH (containing 10% NH4OH) to give a mixture of two regioisomers. The mixture of two regioisomers A and B was resolved by chromatography on a ChiralPak AD-H column eluting with 4-40% MeOH/C02 to give isomer A as the faster eluting isomer and isomer B as the slower eluting isomer. NMR (500 MHz, CD3OD) for isomer B: 57.42 (d, 1H); 4.42 (s, 2H); 4.41 (s, 2H); 4.07 (s, 2H); 1.51 (d, 9H); 1.16 (s, 6H). LC-MS: 226.27 (M+l -56).The desired isomer B was treated with 1 : 1 TF A/CH2CI2 for 1 h to give the title compound. NMR (500 MHz, CD3OD): 67.55 (s, 1H); 4.43 (s, 2H); 4.39 (s, 2H); 4.10 (s, 2H); 1.17 (s, 6H). LC-MS: 182.31 (M+l).

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

The important role of tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

Related Products of 1280210-79-8, These common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-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.

To a suspension of sodium hydride (60% dispersion in oil, 1.55 g, 38.7mmol) in anhydrous acetonitrile (200 mL) was added to tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole- 5(4H)-carboxylate (5.3 g, 25.5 mmol) in one portion under nitrogen at room temperature. The reaction mixture was stirred at room temperature for 2 h. To the resulting white suspension was slowly added cyclopropanesulfonyl chloride (6.9 g, 49.1 mmol) and the mixture was stirred at room temperature for 18 h, quenched with water (120 mL) and the layers were separated. The aqueous layer was then extracted with dichloromethane (2 x 100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material was purified on silica chromatography (300 g Biotage column) and eluted with 15-80% ethyl acetate in hexanes to yield the title compound and tert-butyl 1 -(cyclopentylsulfonyl)-2,6-dihydro^ as a white solid.LC/MS: 314.2(M+1).

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

Brief introduction of 1280210-79-8

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, tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, other downstream synthetic routes, hurry up and to see.

Electric Literature of 1280210-79-8, The chemical industry reduces the impact on the environment during synthesis 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, I believe this compound will play a more active role in future production and life.

Intermediate 2(3.5g, 16.7mmol) dissolved in tetrahydrofuran (35 ml) in, 0 C adding of sodium hydride (1.0g, 25.4mmol, 60%), 30 minutes reaction, adding methyl sulfonyl chloride (2.9g, 25.4mmol) reaction 1 hour. Adding water to the reaction solution (10 ml) in the quenching of the reaction, ethyl acetate (50mL × 2) extraction, the combined organic layer, anhydrous sodium sulfate drying, concentration, silica gel column chromatography for purification (petroleum ether/ethyl acetate (v/v)=1:1), to obtain white solid3a(2.1g, yield 44%).

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO., LTD; ZHANG, CHEN; FAN, JIANG; LI, CAI-HU; WEI, YONG-GANG; (99 pag.)TW2017/8222; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

The important role of tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate

Synthetic Route of 1280210-79-8,Some common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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 vial was charged with [(3R,3aR,6R,6aS)-3-[1-allyl-5-(4-bromophenyl)-6-chloro-imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy-tert-butyl-dimethyl-silane (508.1 mg, 0.837 mmol), tert-butyl 4,6-dihydro-2H-pyrrolo[3,4-c]pyrazole-5-carboxylate (213.1 mg, 1.018 mmol), tripotassium phosphate (603.1 mg, 2.84 mmol), and copper(I) iodide (33.2 mg, 0.174 mmol). The vial was evacuated and backfilled with nitrogen (3×). Trans-N,N?-dimethylcyclohexane-1,2-diamine (53 mul, 0.335 mmol) and dioxane (1.6 ml) were added to the vial to give a pale blue suspension that was heated at 100 C. with stirring for 24 h. The reaction mixture was cooled to room temperature and partitioned between EtOAc (100 ml) and water (100 ml). The aqueous layer was extracted with EtOAc (2×50 ml). The organic layers were combined, washed with brine (1×30 ml), dried over MgSO4, filtered, and evaporated under reduced pressure to give a light green residue. Flash chromatography of the residue utilizing an 40 g silica RediSep Rf column and employing a 0-40% EtOAc/hexane gradient followed by 40% EtOAc/hexane afforded the desired product as a white foam. LC-MS: calculated for C37H47ClN6O6Si 734.3 observed m/e: 735.34 (M+H)+ (Rt 1.47/2 min)

Reference:
Patent; APGAR, James M.; ARASAPPAN, Ashok; BIFTU, Tesfaye; CHEN, Ping; FENG, Danqing; GUIDRY, Erin; HICKS, Jacqueline; KEKEC, Ahmet; LEAVITT, Kenneth; LI, Bing; MCCRACKEN, Troy; SEBHAT, Iyassu; QIAN, Xiaoxia; WEI, Lan; WILKENING, Robert; WU, Zhicai; Merck Sharp & Dohme Corp.; Apgar, James M.; Arasappan, Ashok; Biftu, Tesfaye; Chen, Ping; Feng, Danqing; Guidry, Erin; Hicks, Jacqueline D.; Kekec, Ahmet; Leavitt, Kenneth J.; Li, Bing; McCracken, Troy; Sebhat, Iyassu; Qian, Xiaoxia; Wei, Lan; Wilkening, Robert R.; Wu, Zhicai; US2015/284411; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Discovery of C10H15N3O2

Reference of 1280210-79-8,Some common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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 vial was charged with (3R,3aR,6R,6aR)-6-[5-(4-bromophenyl)-6-chloro-1-(2-trimethylsilylethoxymethyl)-imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol (501.8 mg, 0.861 mmol), tert-butyl 4,6-dihydro-2H-pyrrolo[3,4-c]pyrazole-5-carboxylate (240.3 mg, 1.148 mmol), tripotassium phosphate (581.6 mg, 2.74 mmol), and copper(I) iodide (37.2 mg, 0.195 mmol). The reaction was evacuated (3×) and backfilled with nitrogen. Trans-N,N?-dimethylcyclohexane-1,2-diamine (55 mul, 0.348 mmol) and dioxane (1.7 ml) were added to the vial to give a hazy suspension, which was heated to 100 C. for 24 h. The reaction mixture was then cooled to room temperature and partitioned between EtOAc (100 ml) and water (100 ml). The aqueous layer was extracted with EtOAc (2×50 ml). The organic layers were combined, washed with brine (1×30 ml), dried over MgSO4, filtered, and evaporated under reduced pressure to give a pale green residue. Flash chromatography of the residue utilizing a 40 g silica RediSep Rf column and employing a 0-100% EtOAc/hexane gradient afforded a mixture of the two pyrazole linked regioisomers as a pale amber foam. LC-MS: calculated for C34H43ClN6O7Si 710.27 observed m/e: 711.29 (M+H)+ (Rt 1.30/2 min)