Tag: M.W:100-200

These common heterocyclic compound, 71229-85-1, name is 4-Bromo-1-ethyl-1H-pyrazole, 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. name: 4-Bromo-1-ethyl-1H-pyrazole

To a stirred solution of 6-chloro-7-fluoro-1H-indole 8 (400 mg, 2.36 mmol) in toluene (10 mL) were added 4-bromo-1-ethyl-1H-pyrazole 4 (Step 3 above; 414 mg, 2.36 mmol), potassium phosphate (1.25 g, 5.91 mmol), N,N?-dimethylethylenediamine (84 mg, 0.95 mmol) and Cu(I)I (45 mg, 0.24 mmol) at RT under inert atmosphere. The resulted solution was purged with argon and sealed the tube. The reaction mixture was then heated to 140 C for 16 h. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to RT, dilutedwith hexane (10 mL) and filtered through a short pad of celite. The filtrate was washed with water (2×10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. The crude was purified (silica gel chromatography; 8-10% EtOAc/Hexanes) to afford compound 9 (224 mg, 36%) as a light brown thick liquid. ?H NMR (500 MHz, CDC13): oe 7.64 (s, 1H), 7.61 (s, 1H), 7.31 (d, J = 8.0 Hz, 1H), 7. 12-7.07 (m, 2H), 6.60-6.59 (m, 1H), 4.22 (q, J = 7.5 Hz, 2H), 1.55 (t, J = 7.5 Hz, 3H); LC-MS (ES): 94.7%; m/z 264.1 (M + H); (column: X Select C-18, 50 x 3.0 mm, 3.5 gm); RT 3.87 mm; 5 mMNFI4OAc: ACN; 0.8 mL/min).

The synthetic route of 4-Bromo-1-ethyl-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMAKEA, INC.; BAIN, Gretchen; EVANS, Jillian Frances; HUTCHINSON, John Howard; LONERGAN, David; (123 pag.)WO2016/191427; (2016); 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. 449758-17-2, name is 1-(2-Tetrahydropyranyl)-1H-pyrazole, A new synthetic method of this compound is introduced below., Quality Control of 1-(2-Tetrahydropyranyl)-1H-pyrazole

Step 1: 5-(4-(Benzyloxy)benzyl)-l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazole l-(Tetrahydro-2H-pyran-2-yl)- lH-pyrazole (6.00 g, 39.4 mmol) in THF (180 mL) was cooled to about – 78 C. n-Butyllithium (1.6 M in hexane) (27.1 mL, 43.4 mmol) was added dropwise over about 1 li. The reaction was stirred at about -78 C for about 1 h. l~(Benzyloxy)-4~(bromomethyl)benzene (12.0 g, 43.4 mmol) (prepared in a similar fashion to Preparation 3, step 2 from (4-(benzyloxy)plienyl)methanol) was added and the reaction was allowed to warm to about -50 C. The mixture was diluted with sat. aq. NaHC03 (75 mL) and water (50 mL). The aqueous layer was extracted with DCM (3 x 50 mL). The combined organic layers were dried over MgS04 , filtered, and concentrated. The residue was purified on silica gel (5-20% EtOAc/heptane) to give the title product (10.2 g, 74.3%); LC/MS (Table A, Method j) Rt = 1.77 min; MS m/z: 347 (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; ABBVIE INC.; ARGIRIADI, Maria; BREINLINGER, Eric; DIETRICH, Justin, D.; FRIEDMAN, Michael; IHLE, David; MORYTKO, Michael; MULLEN, Kelly; OSUMA, Augustine; LO SCHIAVO, Gloria, Y.; WILSON, Noel, S.; (303 pag.)WO2016/168633; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 133228-21-4, name is N,N-Dimethyl-1H-pyrazole-1-sulfonamide, 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 133228-21-4, Formula: C5H9N3O2S

Step A: Preparation of3-Bromo-N,N-dimethyl- 1 H-pyrazole- 1-sulfonamide To a solution of N-dimethylsulfamoylpyrazole (44.0 g,0.25 1 mol) in dry tetrahydrofuran (500 mE) at 78 C. wasadded dropwise a solution of n-butyllithium (2.5 M inhexane,105.5 mE, 0.264 mol) while maintaining the temperaturebelow 60 C. A thick solid formed during the addition. Uponcompletion of the addition the reaction mixture was maintained for an additional 15 minutes, afier which time a solution of 1 ,2-dibromotetrachloroethane (90 g, 0.276 mol) intetrahydroffiran (150 mE) was added dropwise while maintaining the temperature below .-70 C. The reaction mixtureturned a clear orange; stirring was continued for an additional15 minutes. The 78 C. bath was removed and the reactionwas quenched with water (600 mE). The reaction mixture wasextracted with methylene chloride (4x), and the organicextracts were dried over magnesium sulfate and concentrated.The crude product was further purified by chromatography onsilica gel using methylene chloride/hexane (50:50) as eluentto afford the title product as a clear colorless oil (57.04 g).?H NMR (CDC13) oe 3.07 (d, 6H), 6.44 (m, 1H), 7.62 (m,1H).

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

Reference:
Patent; E I DU PONT DE NEMOURS AND COMPANY; Berger, Richard Alan; Annan, Isaac Billy; Lahm, George Philip; Flexner, John Lindsey; Selby, Thomas Paul; Stevenson, Thomas Martin; US9173400; (2015); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 82560-12-1,Some common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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.

d. 4-[5-(5-Amino-3-tert-butyl-pyrazol-1-yl)-2-chloro-phenoxy]-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (Intermediate Vd) A microwave vial was charged with 3-tert butyl-1H-pyrazole-5-amine (1.03 g, 7.39 mmol), copper (I) iodide (70.3 mg, 0.37 mmol) and potassium carbonate (2.14 g, 15.5 mmol) and the vial sealed with a septum, evacuated and purged with argon. Trans-N,N’-dimethylcyclohexane-1,2-diamine (210 mg, 1.48 mmol) was then added, then a solution of Intermediate Vc (4.26 g, 8.86 mmol) in toluene (7.5 mL, degassed with argon) was added, and the reaction was subjected to microwave irradiation (150 C. for 1 h). The reaction mixture was then filtered through Celite, and the filtrate concentrated in vacuo. Purification by FCC, eluting with 0-60% EtOAc/cyclohexane, to afford the title compound (2.41 g, 66%). LCMS (Method 3) Rt 4.68 min, m/z 493, 495 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-5-tert-butylpyrazole, its application will become more common.

Reference:
Patent; CHIESI FARMACEUTICI S.p.A.; Alcaraz, Lilian; Hurley, Christopher; Cridland, Andrew Peter; Jennings, Andrew Stephen Robert; US2014/364412; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

26621-44-3, name is 3-Nitro-1H-pyrazole, 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. name: 3-Nitro-1H-pyrazole

To a stirred mixture of 3-nitro-lH-pyrazole (3.16 g, 27.9 mmol) in glacial acetic acid (20 mL) at 0 C was added fuming nitric acid (2.6 mL, 58.69 mmol) dropwise, followed by acetic anhydride (6.6 niL, 69.87 mmol). The mixture was stirred and allowed to warm to rt over 3 h, then poured into ice water (50 mL) and stirred for 20 h. The mixture was extracted with EtOAc combined organic layers were dried over MgS04, filtered and concentrated to dryness to afford 1,3-dinitro-lH- pyrazole (4.3 g, 97%). H NMR (300 MHz, DMSO- 6) delta 8.00 (br s, 1H), 6.44 (br s, 1H).

The synthetic route of 26621-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ROWBOTTOM, Martin; WO2012/30924; (2012); 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. 110860-60-1, name is Methyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate

[Example 4] 5.0 Parts of (Pig-9) synthesized according to Example 2 was added to 70.0 parts of a solvent having the same composition as the azo compound solution in the step (b) of Example 2 and stirred at 20C. Even by stirring for 1 hour, (Pig-9) was not completely dissolved but partially remained undissolved. At this time, a 92 mass% portion of (Pig-9) was dissolved in the solvent. This suspension was added to the poor solvent by the same method as in the step (c) of Example 2 and subsequently, the produced powder was treated in the same manner to obtain 4.8 parts (yield: 96.0%) of (Pig-9). The obtained pigment powder was observed with an eye through a transmission microscope (Electron Microscope JEM-1010, manufactured by JEOL Ltd.), as a result, the length in the long axis direction of the primary particle was 600 nm.

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 110860-60-1.

Reference:
Patent; FUJIFILM Corporation; EP2474574; (2012); 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. 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H3N3O4

Complex CuL2*8H2O was synthesized in the reaction on the warm ethanolic solutions of CuCl2*2H2O and 4-nitro-3-pyrazolecarboxylic acid ligand (L) mixed in molar ratio 1:2. After 2 days, the microcrystalline product was filtered off and washed with ethanol.

According to the analysis of related databases, 5334-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ja?imovi?, ?eljko; Kosovi?, Milica; Kastratovi?, Vlatko; Hollo, Berta Barta; Szecsenyi, Katalin Meszaros; Szilagyi, Imre Miklos; Latinovi?, Nedeljko; Vojinovi?-Je?i?, Ljiljana; Rodi?, Marko; Journal of Thermal Analysis and Calorimetry; vol. 133; 1; (2018); p. 813 – 821;,
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. 6076-12-6, name is Ethyl 4-methyl-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 4-methyl-1H-pyrazole-3-carboxylate

General procedure: A mixture of 1H-imidazole-2-carbaldehyde 40 (200 mg, 2.08 mmol), potassium carbonate (0.8630 g, 6.24 mmol) and 3-(bromomethyl)-1,1′-biphenyl 38 (0.7716 g, 3.12 mmol) in acetonitrile (10 mL) was stirred overnight at room temperature, then the solvent was removed, diluted with water, and extracted with ethyl acetate (3 x 30 mL). The combined organic phases were washed with brine, dried with Na2SO4, filtered, concentrated and purified by silica gel chromatography to afford 44 as a pale yellow solid (527 mg, 97%).

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; Yao, Yiwu; Liao, Chenzhong; Li, Zheng; Wang, Zhen; Sun, Qiao; Liu, Chunping; Yang, Yang; Tu, Zhengchao; Jiang, Sheng; European Journal of Medicinal Chemistry; vol. 86; (2014); p. 639 – 652;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 158001-28-6, name is 5-Amino-1-(tert-butyl)-1H-pyrazole-4-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 158001-28-6, HPLC of Formula: C8H12N4

(a) To a mixture of water (500 ml) and 85% KOH (37.91 g) at 0 C. was added 30% H2 O2 (49.4 ml, 483 mmol), followed by 1-tert-butyl-5-amino-1H-pyrazole-4-carbonitrile (15.83 g, 96.5 mmol). The reaction mixture was stirred for four hours at 0 C. and then at room temperature for 1 hour. A yellow precipitate had formed which was collected by filtration and air dried to afford 13.2 g (75%) of 1-tert-butyl-5-amino-1H-pyrazole-4-carboxamide, m.p. 193-195 C.

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; Sanofi; US5736548; (1998); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6314-23-4, name is 2-(1-Pyrazolyl)ethanol, 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 6314-23-4, COA of Formula: C5H8N2O

General procedure: A flame-dried Schlenk test tube with a magnetic stirring bar was charged with CuI (0.038 mg, 0.0002 mol), Cs2CO3 (0.65 g, 0.002 mol), heterocycle (0.0014mol), 1-bromo-4-methoxybenzene (0.185 g, 0.001 mol) and DMF (10 mL) under N2. A rubber septum was replaced with a glass stopper, and the system was then evacuated twice and back filled with N2. After being stirred at 120 C for 24 h, the reaction mixture was diluted with 2-3 mL of ethyl acetate, filtered through a plug of silica gel, and washed with 30-50 mL of ethyl acetate. The filtrate was concentrated and the resulting residue was purified by column chromatography on silica gel to provide the desired product. A solution of BBr3 (0.23 mL, 0.0025mol) in CH2Cl2 (5 mL) was added dropwise to the solution of 1-(4-methoxyphenyl)-1H-heterocycle (0.001 mol) in CH2Cl2 (10 mL) cooled to 0 C. The resulting solution was stirred for 4 h at room temperature. And the solution was washed by NaHCO3, NH4Cl, NaCl solution in sequence. The CH2Cl2 was dried over anhydrous sodium sulfate, removed under vacuum, and the residue was purified by chromatography on silica gel to yield the 4-(1H-heterocycle -1-yl)phenol.4-(1H-heterocycle -1-yl)phenol (0.001 mol), N,N?-dicyclohexyl carbodiimide (DCC) (0.0012 mol), 4-dimethylaminopyridine (DMAP) (0.0002 mol) in 10 mL chloroform were placed in a Pyrex glass tube, sealed and heated at 80 C for 12 h. After cooling to room temperature, the white solid was filtrated off, and the solvent was removed under vacuum. The crude product was purified by chromatography on silica gel with to gain the desired products.

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-(1-Pyrazolyl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hong, Fengying; Xia, Zhengce; Zhu, Dezhao; Wu, Hongxiang; Liu, Jianhui; Zeng, Zhuo; Tetrahedron; vol. 72; 10; (2016); p. 1285 – 1292;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics