Day: September 26, 2021

Some common heterocyclic compound, 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, molecular formula is C8H14N4O, 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. name: 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide

General procedure: To a solution of aromatic aldehydes 8 (1.0 mmol) in acetonitrile, 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide 10 (1.0 mmol) and InCl3 (10 mol%) were added at room temparature and the reaction mixture was stirred till the completion of the starting materials (indicated by TLC). The solvent was evoparated and the crude product was triturated with 10% diethyl ether in hexane to obtain the pure product. The product was identified by 1H NMR, 13 C NMR and Mass.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 139756-02-8, its application will become more common.

Reference:
Article; Mulakayala, Naveen; Kandagatla, Bhaskar; Ismail; Rapolu, Rajesh Kumar; Rao, Pallavi; Mulakayala, Chaitanya; Kumar, Chitta Suresh; Iqbal, Javed; Oruganti, Srinivas; Bioorganic and Medicinal Chemistry Letters; vol. 22; 15; (2012); p. 5063 – 5066;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C10H7ClN4

General procedure: Equimolar portionsof the intermediate compounds 1 (1 mmol) and the intermediatecompounds 3 (1 mmol) were dissolved in approximately 8 mL ofethanol. The reaction solution was allowed to stir at 80 8C for 2 huntil the reaction was complete. The reaction was monitored byTLC. Mostly, a precipitate formed and was then collected by suctionfiltration.

The synthetic route of 51516-67-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lv, Xian-Hai; Ren, Zi-Li; Li, Dong-Dong; Ruan, Ban-Feng; Li, Qing-Shan; Chu, Ming-Jie; Ai, Cheng-Ying; Liu, Dao-Hong; Mo, Kai; Cao, Hai-Qun; Chinese Chemical Letters; vol. 28; 2; (2017); p. 377 – 382;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

14521-80-3, 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. 14521-80-3, name is 3-Bromo-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-bromo-1H-pyrazole obtained in Step C of Example 6 (600 mg) in N,N-dimethylformamide (40 mL) was added potassium tert-butoxide tetrahydrofuran solution (1 M, 6.12 mL) at room temperature, and the mixture was stirred for 10 min. To the reaction mixture was added 1-chloro-2-(methylsulfonyl)ethane obtained in Step A (873 mg) at room temperature, and the mixture was stirred for 2 hr. To the reaction mixture was added ethyl acetate, and the mixture was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (730 mg). 1H NMR (400 MHz, CDCl3) delta 2.57 (3H, s), 3.63 (2H, t, J = 6.2 Hz), 4.58 (2H, t, J = 6.2 Hz), 6.30 (1H, d, J = 2.0 Hz), 7.43 (1H, d, J = 2.0 Hz)

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; Takeda Pharmaceutical Company Limited; NAGAMIYA, Hiroyuki; YOSHIDA, Masato; SETO, Masaki; MARUI, Shogo; ODA, Tsuneo; ISHICHI, Yuji; SUZUKI, Hideo; KUSUMOTO, Tomokazu; YOGO, Takatoshi; RHIM, Chul Yun; YOON, Cheolhwan; LEE, Gil Nam; KANG, Hyun Bin; KIM, Kwang Ok; JEON, Hye Sun; EP2818473; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 660845-30-7,Some common heterocyclic compound, 660845-30-7, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C6H5ClF2N2O, 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.

In a 500 ml flask, 6.0 g (31 mmol) of 5-chloro-3-(difluoromethyl)-1 -methyl-1 H-pyrazole-4-carbaldehyde are added to 30 ml of toluene. A solution of 2.4 g (62 mmol) of sodium hydroxide in 6 ml of water is added to the reaction mixture, followed by 103 ml of a 30% solution of hydrogen peroxide in water, whilst keeping the temperature below 37 C. After the end of the addition, the reaction mixture is stirred at 50 C for 7 hours. Once the reaction mixture is back to room temperature, the two phases are separated and the organic phase is extracted with 100 ml of water. The combined aqueous phases are acidified to pH 2 with aqueous hydrochloric acid. The resulting white precipitate is filtered, washed twice with 20 ml of water, and dried to yield 3.2 g of 5-chloro-3-(difluoromethyl)-1 -methyl-1 H-pyrazole-4-carboxylic acid as a white solid. H NMR (400 MHz, DMSO-c/6) delta ppm : 3.78 (s, 3H); 7.12 (t, 1 H, JHF = 53.60 Hz)13.19 (s, 1 H); IR (KBr) : 1688 cm”1 (C=0); 2200-3200 cm”1 broad (hydrogen bond).

The synthetic route of 660845-30-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; BENTING, Juergen; DAHMEN, Peter; DESBORDES, Philippe; GARY, Stephanie; HADANO, Hiroyuki; VORS, Jean-Pierre; WACHENDORFF-NEUMANN, Ulrike; WO2012/52491; (2012); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 42027-81-6, The chemical industry reduces the impact on the environment during synthesis 42027-81-6, name is 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, I believe this compound will play a more active role in future production and life.

[0215j A solution of 2-(4-nitro-1H-pyrazol-1-yl)ethanol (2.00 g, 12.73 mmol), 3,4- dihydro-2H-pyran (1.60 g, 19.10 mmol) and p-toluenesulfonic acid (87 mg, 0.51 mmol) in THF (20 mL) was stirred at room temperature for 2 h. Then the mixture was diluted with EtOAc (150 mL), washed with sat. aqueous sodium carbonate (50 mL) and water 60 mL. The organic phase was dried (Na2SO4), filtered and concentrated to give crude product 4-nitro- 1 -(2-((tetrahydro- 2H-pyran-2-yl)oxy)ethyl)-1H-pyrazole as colorless oil (2.00 g, yield: 67%). ESI-MS (M+H) :242.0.

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, 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 309740-49-6, 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. 309740-49-6 name is Methyl 1-methyl-4-nitro-1H-pyrazole-5-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.

General procedure: To a solution of 15a (3.57 g, 16.8 mmol) in MeOH (60 mL) wasadded Pd/C (50% wet, 0.178 g), and the mixture was stirred at room temperature for 2 h under hydrogen atmosphere. The insolublematerials were filtered off by using a pad of Celite, and the Celitewas washed with MeOH. The filtrate was concentrated in vacuo.The residue was diluted with EtOAc, washed with brine, dried overMgSO4, and filtered. The filtrate was concentrated in vacuo toafford 16a

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

Reference:
Article; Kojima, Takuto; Asano, Yasutomi; Kurasawa, Osamu; Hirata, Yasuhiro; Iwamura, Naoki; Wong, Tzu-Tshin; Saito, Bunnai; Tanaka, Yuta; Arai, Ryosuke; Yonemori, Kazuko; Miyamoto, Yasufumi; Sagiya, Yoji; Yaguchi, Masahiro; Shibata, Sachio; Mizutani, Akio; Sano, Osamu; Adachi, Ryutaro; Satomi, Yoshinori; Hirayama, Megumi; Aoyama, Kazunobu; Hiura, Yuto; Kiba, Atsushi; Kitamura, Shuji; Imamura, Shinichi; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2452 – 2465;,
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. 151049-87-5, name is 3-Bromo-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 151049-87-5

(2,6-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (6.0 g, 22.2 mmol, 1.0 eq.), 3-bromo-1-methyl-1H-pyrazole (4.29 g, 26.7 mmol, 1.2 eq.), potassium carbonate (6.23 g, 44.4 mmol, 2.0 eq.) and tetrakis(triphenylphosphine)palladium(0) (487 mg, 0.67 mmol, 0.03 eq.) were combined into a reaction flash under an inert atmosphere. Degassed 1,4-dioxane (92.5 mL) and water (18.5 mL) were added. After 16 h at 100 C., the reaction mixture was diluted with water and extracted with IPA/CHCl3 (1:3) (3*). The combined organic extracts were concentrated under reduced pressure. Purification using flash column chromatography on silica gel with 0-70% MeCN/DCM provided the title compound (3.9 g, 78% yield). 1H-NMR (400 MHz, DMSO-d6) 7.77 (d, J=2.3 Hz, 1H), 7.48-7.42 (m, 2H), 6.83 (d, J=2.3 Hz, 1H), 5.22 (t, J=5.6 Hz, 1H), 4.49 (d, J=5.5 Hz, 2H), 3.88 (s, 3H); ES-MS [M+H]+=225.4.

According to the analysis of related databases, 151049-87-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vanderbilt University; Lindsley, Craig W.; Conn, P. Jeffrey; Engers, Darren W.; Engers, Julie L.; Long, Madeline; Bender, Aaron M.; US2020/131180; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 5203-77-0, 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. 5203-77-0 name is 1,3-Dimethyl-1H-pyrazol-5-ol, 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.

General procedure: To a flame-dried Schlenk tube was added electron-rich aromatic (0.5mmol), CF3SO2Na (118mg, 0.7mmol) dry 1,4-dioxane or CH3CN (1mL). The mixture was heated to 60C by a preheated oil bath. PhPCl2 (125mg, 0.7 mmoL) was added. The reaction mixture was stirred at 70C for the indicated time. Then the reaction mixture was cooled to room temperature. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to afford the pure product.

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; Zhao, Xia; Zheng, Xiancai; Tian, Miaomiao; Sheng, Jianqiao; Tong, Yifan; Lu, Kui; Tetrahedron; vol. 73; 51; (2017); p. 7233 – 7238;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 75415-03-1,Some common heterocyclic compound, 75415-03-1, name is 2-(1H-Pyrazol-3-yl)pyridine, molecular formula is C8H7N3, 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 solution of 2-(1H-pyrazole-3-yl)pyridine (3.02 g, 20.80 mmol) and NBS (3.72 g, 20.90 mmol) in DMF (30 mL) was stirred for 2 h in an ice bath. The reaction mixture was poured into ice water, filtered, and dried in vacuo. The residue (4.38 g, 95% yield) as a white solid was reacted without further purification. 1H-NMR (270 MHz, CDCl3) delta: 11.46 (1H, br s), 8.63-8.65 (1H, m), 8.29 (1H, d, J = 8.4 Hz), 7.78-7.85 (1H, m), 7.64 (1H, s), 7.28-7.33 (1H, m). LC/MS (ESI): m/z 223 [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 2-(1H-Pyrazol-3-yl)pyridine, its application will become more common.

Reference:
Article; Sekimata, Katsuhiko; Sato, Tomohiro; Sakai, Naoki; Watanabe, Hisami; Mishima-Tsumagari, Chiemi; Taguri, Tomonori; Matsumoto, Takehisa; Fujii, Yoshifumi; Handa, Noriko; Honma, Teruki; Tanaka, Akiko; Shirouzu, Mikako; Yokoyama, Shigeyuki; Miyazono, Kohei; Hashizume, Yoshinobu; Koyama, Hiroo; Chemical and Pharmaceutical Bulletin; vol. 67; 3; (2019); p. 224 – 235;,
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. 5071-61-4, name is 5-Phenyl-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 5071-61-4

A solution of acid 4 (0.09 g, 0.47 mmol) in dry DMF (2 mL) treated sequentially with amine (5a-i, 6a-e and 7a-h; 0.517 mmol)and triethylamine (0.94 mmol) was stirred under a N2 atmosphere for 15 min, later TBTU (0.56 mmol) was added and reaction mixture refluxed for 4-10 h. The reaction mixture was quenched with aq satd NH4Cl solution (10 mL). After 10 min, it was diluted withCHCl3 (2 10 mL) and washed with water (10 mL), NaHCO3 solution(10 mL) and brine (10 mL). The organic layers were dried over anhydrous sodium sulfate, evaporated and the residue purified by column chromatography using 30% ethyl acetate in pet. ether to afford corresponding amides 8a-i, 9a-e and 10a-h.

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 5071-61-4.

Reference:
Article; Doma, Anuradha; Kulkarni, Ravindra; Palakodety, Radhakrishna; Sastry, G. Narahari; Sridhara, Janardhan; Garlapati, Achaiah; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 6209 – 6219;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics