Tag: M.W:200-300

Electric Literature of 37687-24-4, The chemical industry reduces the impact on the environment during synthesis 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, I believe this compound will play a more active role in future production and life.

A mixture of diethyl 1H-pyrazole-3,5-dicarboxylate (5.95 g, 28.0 mmol), 2-bromo-1-(2,3-dihydro-1H-inden-5-yl)ethan-1-one (Intermediate 129A, 9.57 g, 70% purity, 28.0 mmol) and potassium carbonate (9.68 g, 70.1 mmol) in acetone (250 ml) was stirred at RT overnight. Then, the mixture was filtered, and the filtrate was concentrated to afford the crude product which was used in the next step without further purification. Yield: 10.4 g (65% of theory, 65% purity). LC/MS [Method 7]: Rt = 1.15 min; MS (ESIpos): m/z = 371 [M+H]+.

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, Diethyl 3,5-pyrazoledicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; MUeLLER, Steffen; SCHOHE-LOOP, Rudolf; ORTEGA, HERNANDEZ, Nuria; SUeSSMEIER, Frank; JIMENEZ NUNEZ, Eloisa; BRUMBY, Thomas; LINDNER, Niels; GERDES, Christoph; POOK, Elisabeth; BUCHMUeLLER, Anja; GAUGAZ, Fabienne, Zdenka; LANG, Dieter; ZIMMERMANN, Stefanie; EHRMANN, Alexander, Helmut, Michael; GERISCH, Michael; LEHMANN, Lutz; TIMMERMANN, Andreas; SCHAeFER, Martina; SCHMIDT, Georg; SCHLEMMER, Karl-Heinz; FOLLMANN, Markus; KERSTEN, Elisabeth; WANG, Vivian; GAO, Xiang; WANG, Yafeng; (801 pag.)WO2019/219517; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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.

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]+. (0114) [0073] Synthesis of 124 and 124-A. To a solution of 123 and 123-A (24.3 mmol, crude product from last step) and A4 (9.3 g, 20.3 mmol) in DMSO (200 mL) was added Na2C03 (21.5 g, 203 mmol), and the reaction mixture was stirred at room temperature for 4 h. The mixture was then diluted with water (400 mL) and extracted with EtOAc (200 mL x 3). The combined organic layers were 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 124 and 124-A (4.5 g, 50%) as a yellow solid. MS 411.0, 413.1 [M+H]+. (0115) [0074] Synthesis of 125 and 125- A . A mixture of 124 and 124-A (500 mg, 1.22 mmol), 5-chlorothiophen-2-ylboronic acid (237 mg, 1.46 mmol) and K2C03 (169 mg, 1.23 mmol) in dioxane/H20 (10 mL/2 mL) was treated with Pd(PPh3)4 (45 mg, 0.06 mmol) under a N2 atmosphere. The reaction mixture was stirred at 50 C for 3 h and then concentrated in vacuo. The residue was taken up in EtOAc (30 mL), and the resulting solution was washed with brine (10 mL x 3). The organic layer was then dried over anhydrous Na2S04 and concentrated in vacuo. The crude residue was purified by Prep-TLC (DCM : MeOH = 20: 1) to give a mixture of 125 and 125-A (450 mg, 82%) as a yellow solid. MS 449.2 [M + H]+. (0116) [0075] Synthesis of Compound 6 and Compound 6A. A mixture of 125 and 125-A (450 mg, 1.0 mmol) and Raney Ni (100 mg) in DCM/MeOH (6mL/6 mL) was stirred at room temperature for 1 h under a H2 atmosphere. Raney Ni was then removed by filtration through Celite, the filtrate was concentrated en vacuo, and the residue was purified by Prep-TLC (DCM : MeOH = 10 : 1). The mixture of regioisomers was then separated by using chiral HPLC (Column: Chiralcel OD-3; Solvent: MeOH; Flow rate: 2 mL/min; RTi843 = 3.477 min, RTi843A = 4.142 min) to give Compound 6 (99 mg, 24%) as a white solid (MS 419.2 (0117) [M+H]+) and Compound 6A (50 mg, 12%) as a white solid. MS 419.2 [M+H]+.

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.

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

Related Products of 285984-25-0,Some common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, molecular formula is C14H19N3, 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.

Example 5 1-(4-((2-((3-Aminobenzo[d]isoxazol-5-yl)amino)pyrimidin-4-yl)oxy) naphthalen-1-yl)-3-(3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)urea To a solution of CDI (56 mg, 0.35 mmol) in DCM (3.0 mL) was added Intermediate A1 (68 mg, 0.24 mmol) and the reaction mixture maintained at RT for 23 hr. The resulting solution was added to a solution of Intermediate B5 (50 mg, 0.098 mmol) in THF (3.0 mL) and the reaction mixture was kept at RT for 2 hr and was then partitioned between EtOAc (30 mL) and saturated aq. NaHCO3 (30 mL). The organic phase was separated and washed with saturated aq. NaHCO3 (30 mL), water (2*30 mL) and brine (2*30 mL), and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 12 g, 0-100% EtOAc in isohexane, gradient elution) to afford tert-butyl (5-((4-((4-(3-(3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)ureido)naphthalen-1-yl)oxy)pyrimidin-2-yl)amino)benzo[d]isoxazol-3-yl)carbamate (62 mg, 81%); Rt 2.88 min (Method 2, acidic); m/z 740 (M+H)+, (ES+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, its application will become more common.

Reference:
Patent; TOPIVERT PHARMA LIMITED; Duffy, Lorna Anne; King-Underwood, John; Longshaw, Alistair Ian; Murray, Peter John; Onions, Stuart Thomas; Taddei, David Michael Adrien; Williams, Jonathan Gareth; Ito, Kazuhiro; Charron, Catherine Elisabeth; US2015/203475; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 866837-96-9, These common heterocyclic compound, 866837-96-9, name is Ethyl 5-amino-1-phenyl-1H-pyrazole-3-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.

1 -Phenyl-5-(3-phenyl-ureido)-1 H-pyrazole-3-carboxylic acid 145,3mg (3,63mmol, 1 ,2Eq) of a 60%suspension of NaH in mineral oil aresuspended in 25ml of dioxane, 700mg (3,03 mmol) of ethyl 5-am ino-1 -^-fluorophenyl)-. H-pyrazole-3-carboxylate are added and the resulting mixture is stirred for 10 minutes at RT: Then phenylisocanate (360, 6mg, 3,03mmol, 1 Eq) is added and the resulting mixture is heated to 80C for 5hours. After cooling 7ml of 1 M NaOH are added and the resulting mixture is stirred overnight at RT. The solvent is evaporated in vacuo and the obtained crude product is subjected to HPLCchromatography. 257mg (26%) of the pure product are obtained.

Statistics shows that Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate is playing an increasingly important role. we look forward to future research findings about 866837-96-9.

Reference:
Patent; SANOFI; RUF, Sven; SADOWSKI, Thorsten; HORSTICK, Georg; SCHREUDER, Herman; BUNING, Christian; OLPP, Thomas; WIRTH, Klaus; WO2012/101199; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1029413-53-3, 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. 1029413-53-3, name is tert-Butyl 3-(4-amino-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Exam pie 20: Synthesis of I -(2-(2-(5-chioro-2-( I -(pyrroi id i n-3-yi)-I H-pyrazoi-4-yiamino) pyrimidin-4-yi)ethyi)phenyi)cyciopropanecarboxamide (20)(a) tert-Butyl 3-(4-(4-(2-(1-carbamoylcyclopropyl)phenethyl) -5-chloropyrimidin-2- ylamino)- 1H-pyrazol- 1-yI)pyrrolidine- 1-carboxylate (A21)A stirred solution of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A 14 (0.150 g, 0.446 mmol), 4-amino-1-(1-Boc-pyrrolidin-3-yl)-1H-pyrazole (0.225 g, 0.892 mmol) in MeOH (10 mL) and water(1.0 mL) was heated at 70 C for 2 days. Additional 4-amino-1-(1-boc-pyrrolidin-3-yl)-1H-pyrazole (0.125 g, 0.446 mmol) was added and the mixture was heated for afurther 16 hours at reflux. After cooling the solvent was removed to afford a crude red oil which was purified by silica gel column chromatography (0-100% EtOAc in cyclohexane) to give the title compound A21 as a red oil (0.164 g, 67% yield). LCMSC: rt 5.51 mm; m/z 551.9 [M+H].

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 3-(4-amino-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; FOITZIK, Richard Charles; MORROW, Benjamin Joseph; HEMLEY, Catherine Fae; LUNNISS, Gillian Elizabeth; CAMERINO, Michelle Ang; GANAME, Danny; STUPPLE, Paul Anthony; LESSENE, Romina; KERSTEN, Wilhelmus Johannes Antonius; HARVEY, Andrew John; HOLMES, Ian Peter; WO2014/26243; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – 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. 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate

Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate 2 (5.1 g, 25 mmol) and KOH (1.68 g, 30 mmol) were added to water (50 mL). The mixture was stirred for overnight, then acidified to pH = 1 using HCl, to give 3 as a white solid that was filtered off and dried with yield 83%, m.p. 200-201 C (Ref. m.p. 204-205 C) [38] , 1H NMR (400 MHz, CDCl3), delta 3.91 (s, 3H, N-CH3), 7.19 (t, J = 54.2 Hz, 1H, -CHF2), 8.31 (s, 1H, pyrazolyl-H), 12.73 (s, 1H, -COOH).

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 141573-95-7.

Reference:
Article; Liu, Xing-Hai; Zhao, Wen; Shen, Zhong-Hua; Xing, Jia-Hua; Xu, Tian-Ming; Peng, Wei-Li; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 881 – 889;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 83-10-3, name is 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, 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 83-10-3, Computed Properties of C12H12N2O3

Step 2) N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide To a suspension of 4-amino-3-fluorophenol (1.0 g, 7.87 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (2.19 g, 9.44 mmol) in CH2Cl2 (20 mL) were added EDCI (3.02 g, 15.7 mmol) and HOAT (0.21 g, 1.57 mmol). The reaction mixture was refluxed for 20 hours, and then cooled to rt. Water (10 mL) was added and the mixture stirred at rt overnight, then filtered and the filter cake was washed with water (5 mL), followed by purifying by a silica gel column chromatography (CH2Cl2/MeOH (v/v)=70/1) to give the title compound as a beige white solid (1.25 g, 46.6%). MS (ESI, pos, ion) m/z: 342.1 [M+H]+, Rt=2.712 min.

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; Sunshine Lake Pharma Co., Ltd.; Calitor Sciences, LLC; Xi, Ning; Wu, Yanjun; Liao, Min; Feng, Yanming; US2015/37280; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 10199-57-2, 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. 10199-57-2, name is 5-Methyl-1-phenyl-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Compounds 19a,b were refluxed for 5 h with 15 mL of thionylchloride. After this time, the mixture was evaporated underreduced pressure to give the appropriate chlorides 20a,b that wereused crude for the next reaction.

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, 5-Methyl-1-phenyl-1H-pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cascioferro, Stella; Maggio, Benedetta; Raffa, Demetrio; Raimondi, Maria Valeria; Cusimano, Maria Grazia; Schillaci, Domenico; Manachini, Barbara; Plescia, Fabiana; Daidone, Giuseppe; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 58 – 68;,
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. 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, A new synthetic method of this compound is introduced below., Product Details of 1082745-50-3

Example 11 B (0.1 g, 0.48 mmol) was mixed with polyphosphoric acid (1.0 g) and 2- (trifluoromethoxy)phenylacetic acid (248 mg, 1.9 mmol) was added. The mixture was heated to 1200C during 16 hours. Temperature was lowered to 200C and the pH value was adjusted to 7 by addition of ammonia (30 % solution in water). The aqueous phase was extracted with dichloromethane (2 x 20 ml_) and the organic phase was dried over sodium sulphate. The crude mixture was purified by flash chromatography. Eluent: hexane/ethyl acetate 40/60. Obtained 23.5 mg (16 %) as a white solid HPLC-MS (I E ) Rt: 6.77 min MS (APCI pos): m/z = 305 (M+H)+

The synthetic route of 1082745-50-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/121919; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, molecular formula is C7H7F3N2O2, 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. SDS of cas: 345637-71-0

To a solution of l-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]piperazine hydrochloride (i.e. the product of Example 7, Step E) (200 mg, 0.57 mmol) and 5-methyl-3- (trifluoromethyl)-l.H-pyrazole-l -acetic acid (0.120 g, 0.57 mmol) in dichloromethane (10 mL) at room temperature was added l-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.110 g, 0.57 mmol), triethylamine (0.086 g, 0.85 mmol) and 1-hydroxy- benzotriazole hydrate (0.020 g, 0.14 mmol). The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with dichloromethane (30 mL), and washed with water (20 mL) and brine (20 mL). The organic layer was dried (Na2SO.;) and concentrated under reduced pressure. The crude residue was purified by column chromatography using 3 % methanol in chloroform as eluant to give 180 mg of the title product, a compound of the present invention as a white solid.1Eta NMR (CDCl3) delta 2.32 (s, 3Eta), 3.29 (m, IH), 3.52 (m, 2H), 3.61 (m, 2H), 3.79-3.72 (m,5H), 4.98 (m, 2H), 5.69 (m,lH), 6.33 (s, IH), 6.93 (s, IH), 7.38-7.28 (m, 5H). Mass spectrum at 505.5 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 345637-71-0, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2008/13622; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics