Tag: M.W:100-200

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. 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H6N2O2

The 1-methyl-1 H-pyrazole-3-carboxylic acid R2a (16 mg, 0.127 mmol, 1 .2 equiv) is dissolved in DMF (2 mL), then TEA (59.1 muIota_, 0.442 mmol, 4 equiv) followed by TBTU (39.2 mg, 0.127 mmol, 1.2 equiv). The reaction mixture is stirred for 15 mins, after which the amine hydrochloride Dc is added in DMF (1 mL). The resulting solution is stirred at RT for 16 h. The solution is then filtered through a Millex filter and purified by prep HPLC. (ammonium bicarbonate/MeOH). The pure fractions are combined, concentrated, frozen and lyophilized to provide compound 1016.FIA M.S.(electrospray) : 808.3 (M-H)- , 810.3 (M+H)+ Retention time (min): 5.4 min1H NMR (400 MHz,DMSO-d6): delta 1 .04 (s, 1 H) , 8.76 (s, 1 H), 7.83-7.80 (m, 2H), 7.76 (d, 1 H, J = 2.0Hz), 7.24 (d, 1 H, J = 7.8Hz), 6.59 (d, 1 H, J = 2.3Hz), 6.45 (s, 1 H), 5.70-5.55 (m, 1H), 5.49-5.43 (p, 1H, J= 6.3Hz), 5.43 (s, 1H), 5.2-5.07 (m, 1H), 4.70-4.50 (m,1H), 4.49-4.40 (m, 1H), 4.39-4.25(m, 1H), 4.03-3.85 (m, 1H), 3.95 (s, 3H), 3.89 (s, 3H), 2.95-2.80 (m, 1H), 2.65-2.55 (m, 1H), 2.35-2.19 (m, 2H), 2.0-1.85 (m, 1H), 1.84-1.66 (m, 1H), 1.65-1.5 (m, 3H); 1.49-1.15 (m, 14H); 1.14-0.94 (m, 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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET, Montse; BORDELEAU , Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63501; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 176969-34-9, 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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 50 mL eggplant-shaped bottle, add 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (0.707 g, 4.01 mmol), add dichloromethane (20 mL), and add oxalyl chloride (1.29 g , 9.96mmol), add 1 drop of N, N-dimethylformamide dropwise, stir at reflux at room temperature, you can clearly see that the reaction solution gradually changed from turbid to clear, TLC followed the reaction, and the reaction ended after 1 hour. The solvent was spin-dried to obtain Intermediate 1, which was dissolved again with dichloromethane (10 mL) and set aside.

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, 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; East China University of Science and Technology; Shao Xusheng; Li Zhong; Fu Wen; Cheng Jiagao; Xu Xiaoyong; Xu Zhiping; (43 pag.)CN111087345; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 632365-54-9,Some common heterocyclic compound, 632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, molecular formula is C5H7N3O2, 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 1-15d (450 mg, 1.50 mmol) in EtOH (30 mL) was added methyl 5-amino- 1H-pyrazole-3-carboxylate (450 mg, 1.90 mmol) at rt. The reaction mixture was heated at 85 C for 4 h, then concentrated under reduced pressure. The afforded crude was purified by column chromatography on silica gel, eluted with 20% ethyl acetate / pet ether which gave the title compound (300 mg) as a solid with 65% LCMS purity.MS (ES+) m/z 372.33 [M+H]+. The compound was used in next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-amino-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; MEDIVIR AKTIEBOLAG; ERSMARK, Karolina; KARLSTROeM, Sofia; KLASSON, Bjoern; LUNDGREN, Stina; ROSENQUIST, Asa; SALVADOR ODEN, Lourdes; (155 pag.)WO2018/226150; (2018); 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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Safety of 1-Methyl-1H-pyrazole-4-carbaldehyde

To a solution of ethyl 2-(diethoxyphosphoryl)acetate (5.4 g, 22.7 mmol, 1 eq) in THF (100 mL) at 0C was added sodium hydride (60 % in mineral oil, 1.2 g, 29.5 mmol, 1.3 eq)portion-wise and the mixture was allowed to stir at the same temperature for 30 minutes. To this mixture was added a solution of 1-methyl-1H-pyrazole-4-carbaldehyde (2.5 g, 22.7 mmol, 1.0 eq) in THF (10 mL) and the resulting mixture was allowed to stir at 0 C for 1 h. Progress of reaction was monitored by TLC. After completion, reaction mixture was diluted with saturated aq. NH4C1 (100 mL) and extracted with ethyl acetate (3 x 100 mL). Combined organic layer waswashed with brine, dried over anhydrous Na2SO4 and evaporated to dryness under vacuum to afford ethyl (E)-3-(1-methyl-1H-pyrazol-4-yl)acrylate (3.9 g, 95 %) which was used in the next step without further purification.

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; AURANSA INC.; PROTTER, Andrew, Asher; GREEN, Michael, John; CHANG, Hak, Jin; PHAM, Son, Minh; CHAKRAVARTY, Sarvajit; LUEDTKE, Gregory, R.; (254 pag.)WO2019/103897; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5203-77-0, name is 1,3-Dimethyl-1H-pyrazol-5-ol, 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 5203-77-0, SDS of cas: 5203-77-0

Intermediate 9 (4 mmol), dissolved in dry dichloromethane( 60 mL), and DCC (4.8 mmol) were mixed together and stirred at room temperature for 1 h. Then 1,3-dimethyl-1H-pyrazol-5-ol (4 mmol) and DMAP (0.4 mmol) were added to the above solution,and stirred for a further 24-36 h at room temperature. After adding dichloromethane (30 mL), the resultant mixture was washed sequentially with 2 N hydrochloric acid (100 mL), saturated NaHCO3 and saturated brine and dried over anhydrous sodium sulfate.The residue solution was evaporated in vacuum and purified by silica gel column chromatography using gradient elution of ethyl acetate/hexane (V/V = 1/2) to obtain the desired intermediate 10.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dimethyl-1H-pyrazol-5-ol, and friends who are interested can also refer to it.

Reference:
Article; Xu, Yu-Ling; Lin, Hong-Yan; Cao, Run-Jie; Ming, Ze-Zhong; Yang, Wen-Chao; Yang, Guang-Fu; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5194 – 5211;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 612511-81-6, These common heterocyclic compound, 612511-81-6, name is (1-Methyl-1H-pyrazol-3-yl)methanamine, 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 4-fluoro-N-methyl-3-nitrobenzamide (350 mg, 1 .766 mmol) in DMF (5 mL) were added (1 -methyl-1 H-pyrazol-3-yl)methanamine (206 mg, 1 .855 mmol) and K2C03 (317 mg, 2.296 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was then quenched with water (10 mL), and the resulting solid was isolated by filtration, washed with water, and dried in vacuum oven for 4 hours to afford N-methyl-4-(((1 -methyl- 1 H-pyrazol-3-yl)methyl)amino)-3-nitrobenzamide (390 mg) as an orange color solid. LC-MS (ES) m/z = 290 [M+H]+. NMR (400 MHz, DMSO-d6): delta 2.76 (d, J = 4.3 Hz, 3H), 3.81 (s, 3 ), 4.57 (d, J = 5.3 Hz, 2H), 6.19 (d, J = 2.0 Hz, 1 H), 7.15 (d, J = 9.1 Hz, 1 H), 7.64 (d, J = 2.3 Hz, 1 H), 7.96 (dd, J = 9.0, 2.2 Hz, 1 H), 8.46 (d, J = 4.8 Hz, 1 H), 8.63 (d, J = 2.3 Hz, 1 H), 8.77 (t, J = 5.6 Hz, 1 H).

The synthetic route of 612511-81-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; MEDINA, Jesus Raul; TIAN, Xinrong; NG DI MARCO, Christina; GRAYBILL, Todd L.; HEERDING, Dirk A.; LI, William Hoi Hong; MANGATT, Biju; MARTYR, Cuthbert D.; RIVERO, Raphael Anthony; (570 pag.)WO2019/49061; (2019); 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. 2075-45-8, name is 4-Bromo-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-1H-pyrazole

To a solution of 4-bromo-1H-pyrazole (3.0 g, 20.4 mmol) in N,N-dimethylformamide (10 mL) was added NaH (60% in mineral oil, 1.0 g, 25 mmol) at 0 C. The reaction mixture was stirred at 0 C. for 10 min. Methyl 2-bromo-2-methylpropanoate (5 mL, 38.67 mmol) was added. The reaction mixture was stirred at room temperature for 1 h before 50 mL of brine was added. The mixture was extracted with ethyl acetate (20 mL*3). The organics were dried with Na2SO4, concentrated and purified by column chromatography (ethyl acetate/petroleum ether, 1:3) to afford methyl 2-(4-bromopyrazol-1-yl)-2-methyl-propanoate (4.7 g, 93.2% yield) as a colorless liquid. LCMS(ESI): [M+H]+=249.0.

According to the analysis of related databases, 2075-45-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1128-54-7,Some common heterocyclic compound, 1128-54-7, name is 3-Methyl-1-phenyl-1H-pyrazole, molecular formula is C10H10N2, 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 suspension of Preparation 137 (2 g, 12.58 mmol) in water (50 mL) and tert-Butanol (2 mL) was heated at 70C and a solution of KMnO4 (4.97 g, 31.45 mmol) in water (120 mL) was dropwise added and mixture stirred at 70C for 12 h. Crude was filtered through Celite, concentrated and acidified with 2 N HCl. Product was extracted with ethyl acetate, organic layers were combined and washed with brine, dried over sodium sulphate, filtered and concentrated to yield the title compound as a white solid (4% yield). LRMS: m/z 189 (M+1)+ Retention time: 2.50 min (Method B) 1H NMR (400 MHz, DMSO-d6) delta ppm 6.96 (d, J=2.34 Hz, 1 H) 7.40 (t, J=7.42 Hz, 1 H) 7.55 (t, J=8.01 Hz, 2 H) 7.90 (d, J=7.82 Hz, 2 H) 8.61 (d, J=2.34 Hz, 1 H) 12.99 (br. s., 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methyl-1-phenyl-1H-pyrazole, its application will become more common.

Reference:
Patent; Almirall, S.A.; Erra Sola, Montserrat; Aguilar Izquierdo, Nuria; Carrascal Riera, Marta; Taboada Martinez, Lorena; Navarro Romero, Eloisa; Vidal Juan, Bernat; EP2390252; (2011); 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. 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, A new synthetic method of this compound is introduced below., Quality Control of 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide

General procedure: We intended to synthesize compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold by using microwave assisted protocol (Scheme 1). In this direction we started the studies for optimization of synthesis of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The optimization studies were initiated by screening of different oxidizing agents as depicted in Table1, see Supplementary data using DMSO:Water in 1:1 proportion to see the conversion in desired product. Amongst all oxidants, the best result was observed with K2S2O8, in equivalence studies for catalyst, 3eq. of catalyst has given maximum yields (Table1, see Supplementary data). Therefore, all reactions were conducted using this condition after optimization of catalyst. However, oxone has also given the product 3a with minor yields. After screening of the catalyst we started study of selectivity for solvent that could affect the formation of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The solvent screening was carried out to find out the best conversion, the mixture of DMSO:H2O in 1:1 proportion has given the best results with excellent yields (Table2, see Supplementary data). The microwave protocols were optimized for this reaction as mentioned in Table 3, see Supplementary data; the reactions carried under different microwave Watt powers have given varied results. Wherein, entry 3(b) (Table3, see Supplementary data) was found to be the best condition for maximum conversion. A series of compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold was synthesized using these optimized conditions, wherein, all kind of substrates with diversity around aryl ring were chosen for conversion and in all cases products obtained in good to excellent yields (Table1).

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; Reddy, G. Lakshma; Guru, Santosh Kumar; Srinivas; Pathania, Anup Singh; Mahajan, Priya; Nargotra, Amit; Bhushan, Shashi; Vishwakarma, Ram A.; Sawant, Sanghapal D.; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 201 – 208;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 5203-77-0, name is 1,3-Dimethyl-1H-pyrazol-5-ol, molecular formula is C5H8N2O, 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. Safety of 1,3-Dimethyl-1H-pyrazol-5-ol

Intermediate 9 (4 mmol), dissolved in dry dichloromethane( 60 mL), and DCC (4.8 mmol) were mixed together and stirred at room temperature for 1 h. Then 1,3-dimethyl-1H-pyrazol-5-ol (4 mmol) and DMAP (0.4 mmol) were added to the above solution,and stirred for a further 24-36 h at room temperature. After adding dichloromethane (30 mL), the resultant mixture was washed sequentially with 2 N hydrochloric acid (100 mL), saturated NaHCO3 and saturated brine and dried over anhydrous sodium sulfate.The residue solution was evaporated in vacuum and purified by silica gel column chromatography using gradient elution of ethyl acetate/hexane (V/V = 1/2) to obtain the desired intermediate 10.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5203-77-0, its application will become more common.

Reference:
Article; Xu, Yu-Ling; Lin, Hong-Yan; Cao, Run-Jie; Ming, Ze-Zhong; Yang, Wen-Chao; Yang, Guang-Fu; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5194 – 5211;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics