Day: August 10, 2021

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. 72760-85-1, name is 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H6N4S

General procedure: A mixture of amino-1H-pyrazole (1 mmol), aldehyde (2 mmol), TMSCN (1.2 mmol) in [Bmim]BF4 (0.5 g) was heated at 120 C for 24 h. After cooling, the reaction mixture was washed with water (5 mL) and the residue washed with MeOH to afford pure product.

According to the analysis of related databases, 72760-85-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Goli, Shokoufe; Mirzaei, Peiman; Bazgir, Ayoob; Journal of the Iranian Chemical Society; vol. 15; 12; (2018); p. 2803 – 2809;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 139756-02-8, 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. 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, This compound has unique chemical properties. The synthetic route is as follows.

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 chemical industry reduces the impact on the environment during synthesis 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide. I believe this compound will play a more active role in future production and life.

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

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. 89717-64-6, name is 4-Bromo-3-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Bromo-3-nitro-1H-pyrazole

To a 50 ml reaction flask by adding 3-nitro-4-bromo -1H-pyrazole (8.9mmol), 2,5-difluorobenzylbromide (9.7mmol), potassium carbonate (26.7mmol) and a catalytic amount tetrabutyl ammonium bromide, adding 20mLN, N-dimethyl formamide, stirring at room temperature 1h. After the reaction is complete the reaction liquid 10 ml water, precipitating a large amount of white solid, filtering, the solid dried to obtain the yellow solid is the product. (Yield 92%)

The synthetic route of 89717-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University; Yang, Shengyong; Wei, Yuquan; (24 pag.)CN105669558; (2016); A;,
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. 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H6N2O

In a 250-mL round-bottom flask, to a solution of 3-methyl- lH-pyrazole-4-carbaldehyde (2.2 g, 18.98 mmol, 1.00 equiv) in DMF (40 mL) was added sodium hydride (60% in oil, l .2g, 30.0 mmol, 1.58 equiv) at 0 C. The mixture was stirred for 1 h at room temperature, and then was added by 4-bromooxane (4 g, 23.03 mmol, 1.21 equiv). The reaction mixture was then stirred overnight at 120 C. When the reaction was done, it was quenched by the addition of water (20 mL) and the mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by reverse phase flash chromatography eluting with MeOH in water (10% to 40% gradient in 60 min) to give a mixture of 3 -methyl- l-(tetrahy dro-2H-pyran-4-yl)-lH- pyrazole-4-carbaldehyde and 5-methyl-l -(tetrahydro-2H-pyran-4-yl)-l H-pyrazole-4- carbaldehyde as yellow oil (1.2 g, 1 :1 , 33%). MS: m/z = 195.2 [M+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 112758-40-4.

Reference:
Patent; MERCK PATENT GMBH; CALDWELL, Richard; LIU-BUJALSKI, Lesley; POTNICK, Justin; NEAGU, Constantin; KULKARNI, Shashank; JONES, Reinaldo; QIU, Hui; (238 pag.)WO2020/43638; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2075-45-8, name is 4-Bromo-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 2075-45-8, HPLC of Formula: C3H3BrN2

To a stirred solution of 4-bromo-1 H-pyrazole in DMF was added sodium hydride at room temperature. The mixture was stirred for 30 minutes, [1,3]dioxolan-2-one was added, the mixture was stirred and slowly warmed to room temperature. The reaction was monitored by TLC. After the reaction was done, EtOAc was added, washed with saturated NaHCO3, water and brine, dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel, eluants EtOAc and DCM 10%, to give 2-(4-Bromo-pyrazol-1-yl)-ethanol 0.22 g, yield 34%. 1H NMR (400 MHz, chloroform-D) 6 ppm 7.49 (s, 1 H) 7.46 (s, 1 H) 4.18 – 4.23 (m, 2 H) 3.93 – 3.98 (m, 2 H) 3.09 (s, 1 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:
Patent; PFIZER INC.; WO2006/21881; (2006); A2;,
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. 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, A new synthetic method of this compound is introduced below., name: tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate

Step D: To 4-chloro-2-[difluoro-(5-fluoro-pyridin-2-yl)-methyl]-8-methylquinazoline (0.255 g, 0.79 mmol) in DMA (2 mL) were added 3-amino-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester prepared according to US2007/219195 (0.31 g, 1.58 mmol) and acetic acid (0.15 mL) and the mixture was heated at 100 C. for 6.5 h. The mixture was allowed to cool to rt and then was purified by reverse phase HPLC using an ammonium acetate modifier. Fraction 1 containing pure product were combined, treated with saturated aq NaHCO3 and concentrated under reduced pressure. The aqueous residue was extracted with DCM and the combined extracts were washed with saturated aq NaHCO3 and brine, dried over MgSO4, filtered, and concentrated under reduced pressure to afford 2-(difluoro(5-fluoropyridin-2-yl)methyl)-8-methyl-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine (28 mg, 13%). 1H NMR (300 MHz, DMSO-d6) delta 12.15 (br s, 1H), 10.57 (s, 1H), 8.67 (s, 1H), 8.50 (d, J=8.3 Hz, 1H), 7.92-8.11 (m, 2H), 7.75 (d, J=7.0 Hz, 1H), 7.52 (t, J=7.6 Hz, 1H), 5.96 (s, 1H), 2.59 (s, 3H), 2.17 (s, 3H); LC-MS (ESI) m/z 385 (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; Hadd, Michael J.; Holladay, Mark W.; Rowbottom, Martin; US2012/53174; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. SDS of cas: 82560-12-1

b. 3-(5-Amino-3-tert-butyl-pyrazol-1-yl)-5-chloro-phenol (Intermediate 62b) A microwave vial containing 3-tert butyl-1h-pyrazol-5-amine (559 mg, 4.02 mmol), Intermediate 62a (1.00 g, 4.82 mmol), copper(I) iodide (38 mg, 0.20 mmol) and potassium carbonate (1.16 g, 8.44 mmol) was repeatedly purged with argon. Trans-N,N’-dimethylcyclohexane-1,2-diamine (126 muL, 0.80 mmol) was added and the mixture was re-purged with argon. Degassed toluene (4 mL) was added and the resulting suspension was stirred and heated at 110 C. for 24 h. The cooled suspension was passed through Celite pad and diluted with water and extracted with EtOAc. The combined organics were dried and concentrated in vacuo. The residue was purified by FCC, using 0-50% EtOAc in cyclohexane, to give the title compound (620 mg, 62%). LCMS (Method 3): Rt 3.13 min, m/z 266 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 82560-12-1, 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

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. name: 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Example A2: Preparation of 3-difluoromethyl-1-methyl-1 H-pyrazole-4-carbonyl chloride:; 69.5 g of thionyl chloride (0.58 mol, 1.17 equivalents) are added at 1100C in the course of 2 hours to a solution of 88 g of 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxylic acid (0.5 mol) in 440 g of chlorobenzene. The reaction mixture is stirred for 1 hour at 1 100C. The reaction mixture is concentrated to a crude product solution. 190 g of 3-difluoromethyl-1- methyl-1 H-pyrazole-4-carbonyl chloride (50% in chlorobenzene, yield: 98%) is obtained. The crude product solution is used without being further purified.

The synthetic route of 176969-34-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG.; SYNGENTA LIMITED.; WO2007/31323; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 25016-11-9, The chemical industry reduces the impact on the environment during synthesis 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

General procedure: 4-(2,3-diamino-5-chloropyridin-4-ylamino)-l,7,7-trimethylbicyclo[2.2.1]heptan-2-one (10) (380mg, 1.23mmol), 1 -methyl- lH-pyrazole-4-carbaldehyde (135mg, 1.23mmol) were taken in EtOH (15ml) to which ammonium acetate (112mg) was added and the reaction mixture was heated at 70C for 48h. Crude LCMS showed the desired product along with trace of starting material. The reaction mixture was allowed to come to rt and the precipitated was filtered and washed well with ethanol to afford the desired product (478mg, 25%) as an off white solid. NMR: delta (, 400M Hz, DMSO-d6): 0.90 (3 H, s), 0.91 (3 H, s), 1.09 (3 H, s), 1.40 – 1.80 (3 H, m), 2.30 – 2.60 (1 H, m), 3.00 – 3.10 (1 H, m), 3.51 – 3.70 (1 H, m), 3.93 (3 H, s), 5.36 (1 H, s), 8.00 (1 H, s), 8.04 (1 H, s), 8.31 (1 H, s), 13.09 (1 H, s). LCMS (254nm): [M+H] + 399.00 (96.43 %). HPLC: 254 nm (94.06 %)

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, 1-Methyl-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CEPHALON, INC.; BRESLIN, Henry J.; CURRY, Matthew A.; GINGRICH, Diane E.; LEARN, Keith S.; OTT, Gregory R.; WAGNER, Jason C.; WO2013/116291; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 3112-31-0

To prepare the salt, the 3,5-pyrazoledicarboxylic acid monohydrate (0.8705 g, 0.005 mol) was treated with a 10 percent hydrazine hydrate in a 1:1 molar ratio (2.5 mL, 0.005 mol) in 50 mL of distilled water. The resulting solution was heated over a water bath for about 20 min to obtain a clear solution. This solution (pH = 3.5) was cooled to room temperature and was placed in a vacuum desiccator over calcium chloride for crystallization. Needle-shaped colorless crystals of the title salt are separated after a week, and the crystals were washed with ice-cold absolute alcohol and air-dried. The salt was soluble in cold water, insoluble in alcohol, and was stable in air (yield: 85 percent). Elemental analysis: C (percent): 28.50 (Cald. 29.12); H(percent): 5.10 (5.23); N (percent): 27.93 (27.16); and hydrazine (percent):15.10 (Cald. 15.52).

The synthetic route of 3112-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Premkumar, Thathan; Srinivasan, Krishnan; Selvakumar, Rajendran; Rath, Nigam P.; Govindarajan, Subbiah; Journal of Thermal Analysis and Calorimetry; vol. 125; 1; (2016);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics