Tag: M.W=0-100

Reference of 28466-26-4,Some common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, molecular formula is C3H5N3, 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 library of compounds in which R4 was various groups having the formula [CONHR »] was prepared by the process described above using 4-fluoro-3-nitrobenzoic acid, as follows: [72] Aldehyde resin was mixed with a primary amine (R17-NH2) in [DICHLOROETHANE] (DCE), triethylorthoformate (TEOF), and DMF (containing [1%] acetic acid) in a 1: 1: 1 ratio. After shaken overnight, sodium triacetoxyborohydride (20 eq. ) dissolved in DMF was added (Abdel-Magid, A. F. , et al., Tetrahedron Lett, 3 1: 5595-5598 (1990) ). After the mixture was shaken at room temperature overnight, the resin was filtered and washed with DMF (3 x 5 mL), [MEOH] [(3 X 5] mL), DMF [(3 X 5] mL), [MEOH] [(3 X 5] mL), and [CH2CL2] [(3 X 5] mL). The resin was washed twice with 5 mL DMF containing [1%] Hunig’s base. To the filtered resin was added a mixture of 4-fluoro-3-nitrobenzoic acid (FNBA, 10 eq. ) and diisopropylcarbodiimide (DIC, 5 eq. ) in 2: 1 DMF : DCM. After shaking at room temperature overnight, the resin was filtered and washed with DMF (3 x 5 mL) and [CH2C12] (3 x 5 mL). [73] The resin was shaken with a primary amine [(R2-NH2)] in DMF for 8 hrs, filtered, and washed with DMF (6 x 5 mL), [MEOH] [(3 X 5] mL), and CH2C12 (3 x 5 mL). The aryl nitro group was reduced by the addition of tin (II) chloride dihydrate (20 eq. , >2 M) and N-methyl morpholine (NMM, 20 eq. ) in N-methyl pyrrolidinone (NMP). After shaken at room temperature overnight, the resin was filtered and washed with NMP (3 x 5 mL), [MEOH] (3 x 5 mL), and [CH2CI2 (3 X 5] mL). The resulting resin was shaken at room temperature with cyanogen bromide (5 eq. ) overnight, filtered, and washed with CH2Cl2 (3 x 5 mL), [MEOH] (3 x 5 mL), and CH2CI2 (3 x 5 mL). To produce a free amine, the resin was shaken for 30 min. in CHCl2 with the addition of sodium methoxide in methanol, filtered, and washed with CH2Cl2 [(4 X 5] mL). [[74]] In the final diversification step, the resin was heated at 500 C in DMF with a mono- substituted epoxide [[RLCH (-CH2O-)].] After shaking for 2 to 4 days the resin was filtered and washed with DMF (5 x 5 mL), [MEOH] [(3 X 5] mL), and CH2Cl2 (3 x 5 mL). T he resin-bound benzimidazole was cleaved from the solid-support by treatment with TFA: [CH2C12] (2: 3) for 1 hour at room temperature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Aminopyrazole, its application will become more common.

Reference:
Patent; Taktix Corporation; WO2003/105779; (2003); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 31108-57-3, These common heterocyclic compound, 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, 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 solution of II-F10 (49.4 mg, 0.1 mmol) and lH-pyrazole-4-carbonitrile (22.3 mg, 0.2 mmol) in acetone (2 mL) was added K2C03 (33.1 mg, 0.24 mmol). After stirring at 20 C for 16 h, the reaction mixture was extracted with EtOAc (3 x 30 mL). The combined organic solution was washed with saturated brine (30 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by flash column (0-20% of EtOAc in PE) to give II- Fll (28.5 mg, 56%) as a solid. (2792) 1H NMR (400 MHz, CDCl3) dH 7.85 (s, 1H), 7.81 (s, 1H), 5.06-4.86 (dd, J= 17.6, 47.6 Hz, 2H) , 2.60 (t, j= 8.8 Hz), 2.27-2.15 (m, 1H), 2.06-1.99 (m, 1H), 1.84-1.67 (m, 6H), 1.56- 1.37 (m, 8H), 1.33-0.80 (m, 13H), 0.67 (s, 3H); LC-ELSD/MS purity 99.30%, MS ESI calcd. for C26H36N30[M-H20+H]+ 406.29, found 406.3.

The synthetic route of 31108-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGE THERAPEUTICS, INC.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, G.; BLANCO-PILLADO, Maria, Jesus; LA, Daniel; HARRISON, Boyd, L.; (646 pag.)WO2019/126761; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 36650-74-5, name is 1H-Pyrazole-3-carbonitrile, 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 36650-74-5, Product Details of 36650-74-5

5 g (53.7 mmol) of 1H-pyrazole-3-carbonitrile were dissolved in 12.5 ml of ethanol and 50 ml of chloroform. With cooling using an ice/acetone bath, gaseous hydrogen chloride was introduced for 50 minutes. The cooling bath was then removed and the mixture was stirred for 3 h. During this time, a solid precipitated out, and this was filtered off and washed with chloroform. Drying under high vacuum gave 7.7 g (81% of theory) of the intermediate ethyl 1H-pyrazole-3-carboximidoate hydrochloride.

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; Bayer Pharma Aktiengesellschaft; STRAUB, Alexander; COLLIN, Marie-Pierre; KOCH, Michael; MEYER, Jutta; SCHLEMMER, Karl-Heinz; NISING, Carl Friedrich; BIBER, Nicole; ANLAUF, Sonja; GROMOV, Alexey; WITTWER, Matthias Beat; (185 pag.)US2016/237059; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, 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 1192-21-8, category: pyrazoles-derivatives

Compound VIII-1 (200 mg, 0.48 mmol) and1-methyl-1H-pyrazole-5-amine (IX-2) (71 mg,0.73mmol) dissolved in tetrahydrofuran (5mL), cooled to -25 C, added 1N LiHMDS (0.73ml, 0.73mmol), reacted at -25 C for about 3h, to be detected by TLC (dichloromethane: methanol = 25:1) The raw material VIII-1 is completely reacted, and the solvent is evaporated under reduced pressure.The residue was subjected to column chromatography (dichloromethane:methanol = 150:1) to afford white powder (yield: 25.1%

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

Reference:
Patent; China Pharmaceutical University; Xu Yungen; Ji Dezhong; Zhang Lingzhi; Zhu Qihua; Bai Ying; Wu Yaoyao; (41 pag.)CN109608444; (2019); A;,
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. 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., Safety of 5-Methyl-1H-pyrazol-3-amine

Intermediate 11: (2-Chloropyrimidin-4-yl)-(5-methylpyrazol-3-yl)amine.; A mixture of 2,4-dichloropyrimidine (0.967 g, 6.49 mmol), 3-amino-5-methylpyrazole (0.63 g, 6.40 mmol), and ethyldiisopropylamine (2.8 mL, 16.22 mmol) in ethanol (13 mL) was stirred at -10 C. for 2 h, then at r.t. overnight, and finally at 50 C. for 3.5 h. The mixture was concentrated to a total volume of approximately 10 mL. Upon repeated addition of diethylether, (2-chloropyrimidin-4-yl)-(5-methylpyrazol-3-yl)amine (0.258 g, 1.23 mmol, 19%) was obtained as colourless crystals. LC/ESI-MS: m/z=210 [M(35Cl)+H]+; m/z=208 [M(35Cl)-H]-; Rt=230 min.

The synthetic route of 31230-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 4SC AG; US2006/142570; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 288-13-1, 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. 288-13-1, name is 1H-Pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(1) 6.81 g (0.1 mol) of pyrazole was dissolved in 50.0% of hydrobromic acid (161.80 g, containing 1.0 mol of hydrogen bromide).Under stirring, the temperature is controlled at 5-15 C., and a 25.0% solution of potassium dichromate 47.07 g is added dropwise.After completion of the dropwise addition, the reaction temperature was controlled at 5-15 C. to allow the reaction system to undergo a bromination reaction. During the reaction, samples were taken at regular intervals and detected by high performance liquid chromatography.When it was detected that the mass of 3-bromopyrazole in the reaction system accounted for 93.0% of the total mass of organic matter in the reaction system, 4.31 g (0.06 mol) of ferrous oxide was added to terminate the reaction to obtain a feed liquid containing 3-bromopyrazole; (2) Add 73.5 g of chlorobenzene to the feed solution, stir and extract for 2 hours, let stand for 1 hour, take the organic phase and allow it to cool down to -15C to -5C,The solids were analyzed by elution from the organic phase. The resulting 12.20 g of solid was 3-bromopyrazole. The yield was calculated to be 83%. After the determination, the main content was 98.5%.

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, 1H-Pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shandong Tianxin Chemical Co., Ltd.; Ju Youguo; Zhao Benteng; Wang Zewu; Yang Hanhua; Zhang Zhaoyuan; Liu Jian; Gong Fangxin; (6 pag.)CN107954913; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 28466-26-4, A common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, molecular formula is C3H5N3, 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 solution of 4-Aminopyrazole (111 mg, 1.00 mmol) in DMF (3.3 mL) in a 20 mL vial was added 2,4-Dichloro-6-trifluoromethylquinazoline (200 mg, 1.00 mmol) and DIEA (258 mg, 2.00 mmol, 0.348 mL). The mixture was heated at 100 C overnight, cooled to rt and poured into water. The precipitate that was formed was filtered and washed with water, dried on the filter for 1 h then in a desiccator overnight to give 227 mg of a grey solid that was used as is in the next step. MS (ES+) m/e 314/316 (M+H)+.

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; KADMON CORPORATION, LLC; LIU, Kevin G.; OLSZEWSKI, Kellen L.; KIM, Ji-In; POYUROVSKY, Masha V.; MORRIS, Koi; YU, Xuemei; LAMARQUE, Christophe; (0 pag.)WO2020/5935; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 31108-57-3, A common heterocyclic compound, 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, molecular formula is C4H3N3, 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.

(5)-3-(4-Cyano- lH-pyrazol- l-yl)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2- methylpropanamide (GeHnF^C (1048) (0909) (0910) [00418] To a solution of lH-pyrazole-4-carbonitrile (0.10 g, 0.001074 mol) in anhydrous THF (5 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.11 g, 0.003223 mol). After addition, the resulting mixture was stirred for 3 h. ( ?)-3-Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (8, 0.377 g, 0.001074 mol) was added to the above solution, and the resulting reaction mixture was allowed to stir overnight at RT under argon. The reaction was quenched by water, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04, filtered, and concentrated under vacuum. The product was purified by a silica gel column using hexane and ethyl acetate (1: 1 to 1:2) as eluent to afford 0.18 g (46%) of the titled compound as white solid. (0911) Compound 1048 was characterized as follows: NMR (400 MHz, DMSO-i delta 10.35 (s, 1H, NH), 8.45 (d, / = 1.2 Hz, 1H, ArH), 8.43 (s, 1H, Pyrazole-H), 8.22 (d, J = 8.8 Hz, J = 1.2 Hz, 1H, ArH), 8.10 (d, J = 8.8 Hz, 1H, ArH), 7.98 (s, 1H, Pyrazole-H), 6.41 (s, 1H, OH), 4.45 (d, / = 14.0 Hz, 1H, CH), 4.36 (d, / = 14.0 Hz, 1H, CH), 1.38 (s, 3H, CH3); mass (ESI, Negative): 362.11 [M- H]-; (ESI, Positive): 386.07 [M+Na]+.

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; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; (234 pag.)WO2017/214634; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, 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 1904-31-0, Safety of 1-Methyl-1H-pyrazol-3-amine

To a mixture of 27 (160 mg, 0.45 mmol), 1-methyl-1H-pyrazol-3-amine (48 mg, 0.49 mmol), Pd2(dba)3 (38 mg, 0.024 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 27 mg, 0.047 mmol) in toluene (5 mL) was added Cs2CO3(220 mg, 0.68 mmol), and the mixture was stirred at 85 °C for 2 h under an argon gas atmosphere. After cooling at room temperature, the mixture was concentrated in vacuo. The residue was purifiedby silica gel column chromatography (0?30percent EtOAc in CHCl3) to give 30b (145 mg, 87percent) as an orange solid. 1H NMR (CDCl3) delta 3.78 (s, 3H), 5.41 (s, 2H), 5.91 (d, 1H, J = 2.2 Hz), 6.51 (dd, 1H, J = 9.5, 2.7 Hz), 7.21 (d, 1H, J = 2.2 Hz), 7.48 (d, 1H, J = 2.6 Hz), 7.54?7.59 (m, 1H), 7.62 (d, 1H, J = 8.5 Hz), 7.73?7.78 (m, 1H), 7.83?7.86 (m, 1H), 8.06 (d, 1H, J = 8.6 Hz), 8.18?8.23 (m, 2H), 10.02 (s, 1H); MS (ESI) m/z 376 [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:
Article; Hamaguchi, Wataru; Masuda, Naoyuki; Isomura, Mai; Miyamoto, Satoshi; Kikuchi, Shigetoshi; Amano, Yasushi; Honbou, Kazuya; Mihara, Takuma; Watanabe, Toshihiro; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7612 – 7623;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35277-02-2, name is 4-Fluoro-1H-pyrazole, 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 35277-02-2, SDS of cas: 35277-02-2

Sodium hydride (60 wt.%, 276 mg, 6.90 mmol) was added to a mixture of 1- (5-chloropyrazin-2-yl)ethanone (800 mg, 5.11 mmol) and 4-Fluoro-1H-pyrazole (484 mg, 5.62 mmol) in N,N-dimethylformamide (6.0 mL) at ambient temperature for 10 minutes. The reaction mixture was then poured into water (70 mL) and was sonicated and stirred for 20 minutes. A dark red solid was isolated by filtration, washed with small amounts of water, and dried to 1-(5-(4-fluoro-1H-pyrazol-1-yl)pyrazin-2-yl)ethan-1-one (919 mg, 95% yield). MS: M+1 = 207.

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

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason D.; GUZI, Timothy; WILSON, Kevin J.; DIPIETRO, Lucian V.; ZHANG, Yulian; WILSON, Douglas; FLEMING, Paul E.; (137 pag.)WO2018/17983; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics