Day: June 9, 2021

Related Products of 4149-06-8, 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. 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The mixture of alpha,beta-unsaturated ketone 1, or 4 (1.0 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one 2 (1.0 mmol), p-TSAxH2O (0.3mmol), MeCN (4mL), H2O (4mL) was put in a reaction flask under 80 C about 1-3 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be precipitated out at same time. Then, it was filtered, washed thoroughly with MeCN. The products were recrystallized from DMF.

The chemical industry reduces the impact on the environment during synthesis 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Xu, Shuangshuang; Wang, Zhansheng; Li, Xiuling; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 72; 38; (2016); p. 5754 – 5761;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 49633-25-2, name is 3-Isopropylpyrazole, 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. Computed Properties of C6H10N2

Following the procedure of Example 36, Part B, but substituting 3-isopropylpyrazole for 4-bromo-3-isopropylpyrazole, there was prepared 3-isopropyl-N,N,alpha-trimethylpyrazole-1-acetamide having a boiling point at 83 C. at 0.03 mm Hg. About 10% of the 5-isopropyl-N,N,alpha-trimethylpyrazole-1-acetamide isomer was present.

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

Reference:
Patent; The Upjohn Company; US3957480; (1976); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 154471-65-5, These common heterocyclic compound, 154471-65-5, name is 1-Methyl-3-(trifluoromethyl)-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.

Chemical synthesis of compound 16677. For synthesis of compound 16677, 1-methyl-3-trifluoromethyl-5-pyrazolecarboxylic acid 3 (Scheme 1, FIG. 10) was prepared from commercially available compound 1 as previously described (Schlosser et al., (2002) Eur. J. Org. Chem. 2002(17), 2913-2920). Compound 3 (820 mg, 4.2 mmol) in dichloromethane (10 ml) was treated with oxalyl chloride (2.0 M in CH2Cl2, 8.5 mmol, 4.2 ml) and a catalytic amount of DMF. The reaction mixture was incubated at room temperature for 5 hours. Evaporation of solvent delivered yellow acyl chloride 4 in quantitative yield.

The synthetic route of 154471-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 25016-11-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 25016-11-9 as follows.

Potassium terf-butoxide (23.47 g of 95%, 199.1 mmol, 2.44 equiv.) was suspended in anhydrous DME (90 mL) and cooled to – 60 0C. TosMIC (23.76 g, 121.7 mmol, 1.49 equiv.) was dissolved in anhydrous DME (75 mL), and this was added drop-wise to the potassium terf-butoxide solution over 20 minutes. After stirring for 20 minutes between – 60 and – 55 0C, the compound of formula IX, in anhydrous DME (55 ml_), was added over 23 minutes. The reaction was stirred one hour at – 55 to – 50 0C to yield a thick suspension. Methanol (90 ml_) was then added resulting in a clear brown solution. The cooling bath was removed, and after stirring 5 minutes in air, the reaction flask was immersed in an oil bath preheated to 85 0C. The reaction was stirred for 1 hour. After cooling, the mixture was concentrated and the resulting tan solid was dissolved in water (180 ml_) with acetic acid (9 ml_). This was extracted with ethyl acetate (3 x 250 ml_), and these extracts were combined, washed with saturated aqueous sodium chloride (100 ml_), dried over sodium sulfate, filtered and concentrated to yield a brown oil (13.71 g). This oil was dissolved in dichloromethane and purified by silica-gel chromatography using a gradient from 0% to 15% dichloromethane-acetone to yield the compound of formula Xl as a bright yellow oil (7.89 g, 63% yield).

According to the analysis of related databases, 25016-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; WO2008/153870; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 64517-88-0, A common heterocyclic compound, 64517-88-0, name is 1,3-Dimethyl-1H-pyrazol-4-amine, molecular formula is C5H9N3, 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.

[6]; 2-(6-Chlorobenzotriazol-l-yl)-l,l,353-tetramethyluronium tetrafluoroborate was used in place of 2-(7-azabenzotriazol-l-yl)-l,l,353-tetramethyluronium hexafluorophosphate(V) as the coupling agent. The product gave the following characterising data :- 1H NMR Spectrum: (DMSOd6) 2.12 (s, 3H), 3.66 (s, 2H), 3.7 (s, 3H), 3.78 (s, 3H)5 4.02 (s, 3H)5 6.51 (d, IH), 6.88 (m, IH)5 7.03 (d, IH), 7.22 (s, IH)5 7.35 (d, IH)5 7.81 (s, IH), 8.77 (d, IH)5 9.43 (s, 2H); Mass Spectrum: M+H+ 434.

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1146629-77-7, name is (4-(1H-Pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate, 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 1146629-77-7, Formula: C15H17N5O2

To a solution (15 mL) of 37 (514 mg, 1.72 mmol, preparation described in Lin, Q. et al. Org. Lett., 2009, 11, 1999-2002) in acetonitrile was added 44 (537 mg, 4.29 mmol) , Then DBU (540 muL, 3.61 mmol) was added. The reaction was stirred at room temperature for 15 h and then concentrated under reduced pressure. The resulting crude mixture was diluted with water and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with 1 N HCl, dried (Na 2 SO 4), filtered and concentrated under reduced pressure. Purification by normal phase column chromatography (SiO 2, 0 to 60% ethyl acetate / hexane) gave (+/-) 45 as a white foam (368 mg, 50%)

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, (4-(1H-Pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Concert Pharmaceuticals Inc.; Zhou, Haibing; Peng, Xueke; Hu, Zhiye; Ning, Wentao; Dong, Chune; (43 pag.)JP2018/172421; (2018); 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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., Safety of 1-Methyl-1H-pyrazol-5-amine

(S)-7-(2-chloro-5-methylpyrimidin-4-yl)-3-methyl-2-((2-methyl-2H- 1 ,2,3-triazol-4- yl)methyl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (211)-one (190 mg, 0.51 mmol), 1-methyl- 1H-pyrazol-5-amine (54.6 mg, 0.56 mmol), cesium carbonate (333 mg, 1.02 mmol) and BrettPhos 3rd generation pre-catalyst (23.16 mg, 0.03 mmol) were suspended in tertbutanol (6mL) and de-gassed for 10 minutes. The reaction was heated to 80 °C for 18hours under nitrogen. Reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate (25 mL), dried over sodium sulfate and concentrated in vacuo to give a yellow solid. The crude product was dissolved in DMSO (5 mL), filtered and purified by preparative HPLC (Waters XBridge Prep C18 OBD column, Sji silica, 30 mm diameter, 100 mm length),using decreasingly polar mixtures of water (containing 1percent NH3) and MeCN as eluents.Fractions containing the desired compound were evaporated to dryness to afford (S)-3-methyl-7-(5 -methyl-2-(( 1-methyl-i H-pyrazol-5 -yl)amino)pyrimidin-4-yl)-2-((2-methyl-2H- 1,2,3 -triazol-4-yl)methyl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (211)-one (102 mg, 46.2percent) as a white solid. ?H NMR (500 MHz, DMSO, 30 °C) 1.15 (3H, d), 2.33 (3H, s), 3.70(3H, s), 3.9 – 4.01 (1H, m), 4.12 (3H, d), 4.14 – 4.32 (2H, m), 4.35 (1H, d), 5.08 (1H, d),6.27 (1H, d), 7.26 (1H, d), 7.34 (1H, d), 7.64 (1H, d), 7.69 (1H, s), 8.24 (1H, s), 9.08 (1H,s). mlz: ES+ [M+H]+ = 433.

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; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 15878-00-9,Some common heterocyclic compound, 15878-00-9, name is 4-Chloro-1H-pyrazole, molecular formula is C3H3ClN2, 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 83 trans-4-Chloro-2′-cyclopropyl-2’H-[1,3′]bipyrazolyl-4′-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide Sodium hydride (60% in oil; 57 mg, 1.43 mmol) was added to a solution of 4-chloro-pyrazole (148 mg, 1.43 mmol) in dry DMF (25 mL) under nitrogen at 0 C. in an ice-water bath and the mixture was heated to 40 C. for 1 h. trans-5-Chloro-1-cyclopropyl-1H-pyrazole-4-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide (60 mg, 0.18 mmol) was added and the mixture was heated at 110 C. overnight and then cooled. After the DMF was evaporated in vacuo, water and dichloromethane were added. The organic layer was separated, and the aqueous phase was extracted three times with dichloromethane. The combined organic phases were concentrated in vacuo and the residue was purified by C-18 reverse phase preparative-HPLC with a gradient of 10-90% acetonitrile/water to give trans-4-chloro-2′-cyclopropyl-2’H-[1,3′]bipyrazolyl-4′-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide (56 mg, 77%). LRMS m/z calcd for C20H24ClN5O2 (M+H) 402.2, found 402.2.

The synthetic route of 15878-00-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anderson, Kevin William; Fotouhi, Nader; Gillespie, Paul; Goodnow, Robert Alan; Guertin, Kevin Richard; Haynes, Nancy-Ellen; Myers, Michael Paul; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Rossman, Pamela Loreen; Scott, Nathan Robert; Thakkar, Kshitij Chhabilbhai; Tilley, Jefferson Wright; Zhang, Qiang; US2007/225280; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 58607-90-2,Some common heterocyclic compound, 58607-90-2, name is Ethyl 5-oxo-4,5-dihydro-1H-pyrazole-3-carboxylate, molecular formula is C6H8N2O3, 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.

[00230] To a solution of ethyl 5-oxo-4,5-dihydro-1 H-pyrazole-3-carboxylate (9.5 g , 60.8 mmol) in DCM and DMF (Volume: 1 25.5 ml, Ratio: 7:1 ) was added imidazole (6.21 g, 91 mmol) and TBDMSCI (1 0.09 g, 66.9 mmol) at 0 C. The reaction mixture was warmed up to room temperature and stirred for overnight. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered off, and dried in vacuo. The crude product was used for the next step without further purification. LCMS (m/z) : 271 [M+H]+. 1 H NMR (500 MHz, CDCI3) : (0402) 6.16 (s, 1 H), 4.37 (d, J=7.09 Hz, 2H), 1 .38 (t, J=7.09 Hz, 3H) , 0.98 (s, 9H), 0.27 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 5-oxo-4,5-dihydro-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; NOVARTIS AG; FU, Jiping; HAN, Wooseok; JIN, Xianming; PFISTER, Keith Bruce; YOUNG, Joseph Michael; (68 pag.)WO2019/123285; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1453-58-3, A common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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.

A stirred solution of 3-methylpyrazole (82.1 g, 1.0 mol) in water (3.5 L) was heated to 70 °C. Potassium permanganate (111 g, 0.70 mol) was added in one portion, keeping the temperature near 70 °C. The reaction mixture was stirred for 1 h at 70 °C, and then a second portion of potassium permanganate (111 g) was added at 70 °C. After 1 h, a final portion of potassium permanganate (111 g) was added at 70 °C. The reaction mixture was stirred a further 2 h at 70 °C, and any unreacted oxidant was reduced by the dropwise addition of isopropanol. The reaction mixture was cooled to room temperature, filtered, the solid was rinsed with water, and the filtrate evaporated to 500 ML. The aqueous was chilled to 0 °C, acidified with concentrated HCI, filtered, the solid product washed with water, and dried under vacuum to provide pyrazole- 3-carboxylic acid as a white solid (64.4 g, 57percent).

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; MERCK & CO., INC.; WO2004/58702; (2004); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics