Day: August 6, 2021

Adding a certain compound to certain chemical reactions, such as: 95162-14-4, name is 4-Bromo-1-tritylpyrazole, 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 95162-14-4, Computed Properties of C22H17BrN2

A mixture of 4-bromo-4-trityl-1H-pyrazole (4.8 g, 12.3 mmol) described in Manufacturing Example 32-1-1, bis(pinacolate)diboran (5.0 g, 19.7 mmol), potassium acetate (3.62 g, 36.9 mmoL), 1,1′ bis(diphenylphosphino)ferrocene dichloropalladium(II) (450 mg, 0.62 mmol) and dimethyl sulfoxide (50 mL) was stirred under argon atmosphere for 17 hours and 10 minutes at 80 C. The reaction solution was allowed to room temperature, and partitioned into water and ethyl acetate. The organic layer was concentrated under a reduced pressure. The residue was purified by silica gel chromatography (heptane:ethyl acetate=4:1). Heptane was added to the solids obtained by concentrating the eluate under a reduced pressure, which were then irradiated by ultrasonic wave and filtered to obtain the title compound (1.51 g, 28.0%). 1H-NMR Spectrum (CDCl3) delta (ppm): 1.30 (12H, s), 7.10-7.16 (6H, m), 7.26-7.31 (9H, m), 7.75 (1H, s), 7.94 (1H, s).

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-Bromo-1-tritylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/105904; (2007); 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. 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate, A new synthetic method of this compound is introduced below., Safety of Ethyl 4-iodo-1H-pyrazole-5-carboxylate

60% sodium hydride (99 mg) was added to a solution of the compound 0215-2 (0.50 g) and iodomethane (0.23 mL) in tetrahydrofuran (2.0 mL) at 0C, and the mixture was stirred at room temperature for 0.5 hours. To the reaction solution, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and then dried over sodium sulfate. The solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain a compound 0215-2 (0.37 g) as a colorless oily substance. – Synthesis of Compound 0219 – (Synthesis of Compound 0219-1) The same method as in Example 215 except for using (2-(trimethylsilyl)ethoxy)methyl chloride instead of iodomethane used for the synthesis of the compound 0215-2 in Example 215 was used to obtain a compound 0219-1 (0.273 g) as a position isomer mixture (colorless oily substance). (Synthesis of Compound 0219-2) The same method as in Example 214 except for using the compound 0219-1 instead of tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate used for the synthesis of the compound 0214-2 in Example 214 was used to obtain a compound 0219-2 (0.22 g) as a position isomer mixture (pale yellow solid). MS m/z (M+H): 525. A 1 M aluminum lithium hydride solution in diethylether (24 muL) was added to a solution of the compound 0215 (5.0 mg) in tetrahydrofuran (1.0 mL) at room temperature, and the mixture was stirred for 0.5 hours. To the reaction solution, a saturated aqueous ammonium chloride solution and methanol were added, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-methanol) to obtain a compound 0216 (4.5 mg). (Synthesis of Compound 0219-3) The same method as in Example 216 except for using the compound 0219-2 instead of the compound 0215 used for the synthesis of the compound 0216 in Example 216 was used to obtain a compound 0219-3 (59 mg) as a position isomer mixture (brown solid). MS m/z (M+H): 483.

The synthetic route of 179692-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; FURUYA, Kentarou; TERAO, Takahiro; SEKINE, Shinichirou; NAKAGAWA, Daisuke; EP2727920; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 4522-35-4, 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 4522-35-4 as follows.

To a solution of 3-iodopyrazole (0.70 g, 3.61 mmol), in DMSO (18.0 mL) wasadded sodium hydride (60% disp. in oil, 0.173 g, 4.33 mmol), and the resultingmixture was stirred for 0.5 h before adding 4-fluoro-2-trifluoromethyl pyridine(0.596 g, 3.61 mmol). The reaction mixture was stirred at 90 oc for 3 h. Thereaction was quenched by the addition of water and extracted with EtOAc. Thecombined organic extracts were washed with water and brine, dried overMgS04 and concentrated in vacuo. The crude mixture was purified by flashchromatography (ISCO, 40 g, 0-50 % EtOAc in hexanes) to afford 4-(3-iodo-1H-pyrazol-1-yl)-2-(trifluoromethyl)pyridine, as a white solid. LCMS calc. =339.95; found= 339.93 (M+H)+. 1H NMR (500 MHz, CDCh): o 8.77 (d, J=5.3 Hz, 1 H); 8.03 (d, J = 3.8 Hz, 1 H); 7.91 (d, J = 2.6 Hz, 1 H); 7.77 (d, J =5.4 Hz, 1 H); 6.74 (d, J= 2.5 Hz, 1 H).

According to the analysis of related databases, 4522-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; CHEN, Yi-Heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; KATSUNO, Mika; WO2014/99695; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 25699-83-6, The chemical industry reduces the impact on the environment during synthesis 25699-83-6, name is 4-(1H-Pyrazol-1-yl)benzonitrile, I believe this compound will play a more active role in future production and life.

To 4-(pyrazol-1-yl)benzonitrile (see WO 2005/095343A) (1.46 g, 8.63 mmol) was added a solution of 1M borane tetrahydrofuran complex in tetrahydrofuran (93 ml, 93 mmol), followed by heating to reflux for 16 hours. After completion of the reaction, methanol (14 ml) was added to the reaction solution, followed by concentration under reduced pressure. 6N Hydrochloric acid (265 ml) was added to the residue, followed by further heating to reflux for 3 hours. After this solution was concentrated under reduced pressure, a small amount of water was added. The resulting solution was adjusted to pH 11 with a 30% aqueous sodium hydroxide solution under ice cooling, followed by extraction with methylene chloride. The separated organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; chloroform:methano1:28% aqueous ammonia=90:10:1 (V/V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.24 g) as a pale yellow solid. (Yield: 83%) Mass spectrum (CI, m/z): 174 (M++1). 1H-NMR spectrum (CDCl3, ppm): 7.91 (dd, J=2.5, 0.5Hz, 1H), 7.72 (d, J=1.6Hz, 1H), 7.69-7.63 (m, 2H), 7.44-7.37 (m, 2H), 6.46 (dd, J=2.5, 1.6Hz, 1H), 3.91 (s, 2H).

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-1-yl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ube Industries, Ltd.; EP2264009; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-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 120068-79-3, Recommanded Product: 120068-79-3

Example 11; Sulfinylation of 5-amino-1 -[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H- pyrazole-3-carbonitrile with thionylchloride, triethylamine hydrochloride and dosage of potassium trifluoromethylsulfinateWithin a 750 mL reactor with a mechanical stirrer and a thermometer were placed vac- uum dried triethylamine hydrochloride (51.1 g, 368 mmol), 147 g anhydrous toluene(6.5 molar equivalents relative to 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H- pyrazole-3-carbonitrile), and thionylchloride (35.7 g, 294 mmol) under an argon atmosphere. After cooling to 00C to 5 0C with external cooling, vacuum dried potassium trifluoromethylsulfinate (50.4 g, 296 mmol) was added in three equal portions every 10 min while keeping the reaction temperature below 5 0C. After stirring for another 30 min, vacuum dried 5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-1 H-pyrazole-3- carbonitrile (79.5 g, 245 mmol, 99 % purity) was added at 5 0C, and the reaction mixture was kept at 5 0C for 60 min and then heated to 35 0C within 45 min. The temperature of 35 0C was kept for another 10 hours before quenching the reaction with 200 g of sodium hydroxide solution (10 wt.%).The resulting suspension was diluted with 176 mL of ethylacetate. After phase separation the organic layer was washed once with sodium hydroxide solution (10 wt.%). After phase separation, the organic layer was analyzed by quantitative HPLC (79 % yield). The content of compound F was below 2.9 weight percent in the crude mixture (without solvent). The product was crystallized from a mixture of ethylacetate and toluene affording the title compound as a white crystalline powder (77.1 g, 75 % yield, 98 % purity by quantitative HPLC).; These experiments Ca and Cb where compared to examples 18 and 19, which were conducted as described above for example 11 , employing potassium trifluoromethyl- sulfinate / pyridine hydrochloride / SOCb and potassium trifluoromethylsulfinate / trimethylamine hydrochloride / SOCb as reagents.

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, 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF SE; WO2008/55877; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 7119-95-1, name is 1-Nitropyrazole, 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. HPLC of Formula: C3H3N3O2

Concentrated sulphuric acid (80 ml) was added dropwise to a stirred sample of 1-nitropyrazole (20.3 g) that was cooled in an ice-bath. The resultant mixture was stirred for 16 hours and allowed to warm to ambient temperature. The mixture was poured onto ice and stirred for 20 minutes. The resultant solid was isolated and washed with water. The filtrate was neutralised by the addition of potassium carbonate and extracted with diethyl ether. The recovered solid was added to the diethyl ether solution and the resultant solution was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulphate and filtered. Petroleum ether (b.p. 60-800C) was added to the filtrate which was concentrated by evaporation to a volume of about 50 ml. A precipitate formed which was isolated by filtration. There was thus obtained 4-nitropyrazole (16 g); 1H NMR: (DMSOd6 + CF3CO2H) 8.57 (s, 2H).

The synthetic route of 1-Nitropyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/99317; (2007); 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. 25711-30-2, name is 1,5-Dimethyl-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,5-Dimethyl-1H-pyrazole-4-carbaldehyde

A mixture of 1 ,5-dimethyl-1 H-pyrazole-4-carbaldehyde (Zhurnal Obshchei Khimii 1980, 50, 2370-5, 2.0 g, 16,1 mmol), terf-butylsulfinamide (2.05 g, 16.9 mmol), and Ti(OEt)4 (6.76 ml, 32.2 mmol) in THF (32 ml) was heated under reflux for 18 h under nitrogen. After being cooled to rt, the mixture was poured into brine (32 ml) with stirring. The resulting suspension was filtered through a plug of Celite, and the filter cake was washed with EtOAc. The filtrate was transferred to a separation funnel, and organic layer was washed with brine. Then the aqueous layer was washed with EtOAc and the combined organic extracts were dried over Na2SO4, and concentrated in vacuo. The crude material was purified by silica gel chromatography (CH2CI2:MeOH=50:1-30:1 ) to give the desired product as a white solid (3.55 g, 97% yield). 1H NMR (300 MHz, CDCI3) delta 1.23 (9H, s), 2.52 (3H, s), 3.83 (3H, s), 7.81 (1H, s), 8.49 (1H, s). MS (ESI) m/z 228 (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 25711-30-2.

Reference:
Patent; PFIZER JAPAN INC.; PFIZER INC.; RENOVIS, INC.; WO2008/59370; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5334-39-4, These common heterocyclic compound, 5334-39-4, name is 3-Methyl-4-nitro-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.

To a solution of 5-hydroxy-l-methyl-piperidin-2-one (175 nig, 1.35 mniol) , 3 -methyl -4-nitro-lH-pyrazole (5) (205.9 rag, 1.62 mmol) and PPh3 (531.14 mg, 2.03 mmol) in THF (15 mL) was added DIAD (409.48 mg, 2.03 mmol) at 0 C. The mixture was stirred at 25 C for 12 h. The reaction mixture was concentrated under reduced pressure to get a residue, which was purified by prep-TLC (Si02, DCM: MeOH :=: 20: 1) to give a mixture of l-methyl-5-(5-methyl-4-nitro-lH- pyrazol-l-yl)piperidin-2-one and l-methyl-5-(3-methyl-4-iiitro-lH-pyrazol-l-yl)piperidin-2-one as yellow solid, LCMS: RT 0,577 min, m/z = 239.1 [M+H . To a mixture of l-methyl-5-(5-methyl-4-nitro-lH-pyrazol- l-yl)piperidin-2-one and l-methyl-5-(3-methyl-4-nitro-lH-pyrazol-l-yl)piperidin-2-one (180 mg, 755.54 muetaiotaomicron) in MeOH (10 mL) was added Pd/C (10%, 60 mg) under 2. The suspension was degassed and purged with H2 for 3 times. The mixture was stirred under H2 (15 Psi) at 25 C for 4 h. It was filtered over celite, the filter cake was washed wtih MeOH (20 mL chi 2), the filtrate was combined and concentrated under reduced pressure to give a mixture of 5-(4-amino-5-meth}7l-lH-pyrazol-l-yl)-l-methylpiperidin-2- one and 5-(4-amino-3-methyl-lH-pyrazol-l -yl)-l -methylpiperidin-2-one (as yellow oil. LCMS: RT 0.194 mm, m/z = 209.1 [M+H]+. A mixture of 5-(4~amino-5~ methyl- lH-pyrazol-l-yl)-l-methylpiperidm-2-one and 5-(4-amino-3-methyl-lH-pyrazol-l-y])-l- methylpiperidin-2-one (107 mg, 513.78 mupiiotaomicron), 4-cyclopropyl-2-methylsulfonyl-5- (trifluoromethyl)pyrimidine (137 mg, 513.78 muetaiotaomicron) and TsQH.HjQ (49 mg, 256.89 mupiiotaomicron) in 1,4-dioxane (15 mL) was degassed and purged with N2 for 3 times, and then the m ixture was stirred at 100 C for 2 h under N2. It was poured into H20 (15 mL), adjusted to pH = 8 with aq, NaHC03, extracted wtih EtOAc (2 x 30 mL). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure to get a residue, which was purified by prep-HPLC (neutral) first and then it was re- purified by SFC to give 5-(4-((4-cyclopropyl-5-(trifluoromethyl)pyrimidin-2-yl)amino)-5-methyl-lH- pyrazol-1 -yl)-l -methylpiperidin-2-one (14 mg) and 5-(4-((4-cyc]opropyl-5-(tri£luoromethyl)pyrimidin-2- yl)amino)-3 -methyl- 1 H-pyrazol- 1 -yl)- 1 -methylpiperidin-2-one . 5-(4-((4-cyclopropyl-5-(trifluoromethyl)pyrimidin-2-yl)amino)-5-methyl-lH-pyrazol-l-yl)-l- methylpiperidin-2-one (A-26): H MR (400 MHz, CDC13): 3 8.39 (s, IH), 7.67 (br, s . 1H), 6.51 (br. s, H), 4.42 – 4.60 (m, IH), 3.91 (dd, J = 1 1.69, 9,92 Hz, 1H), 3.46 (ddd, J = 12.13, 5 ,51 , 1 ,76 Hz, IH), 3.00 (s, 3H), 2.65 (d, J ——- 3.97 Hz, 1H), 2.42 – 2.59 (m, 11 1 ). 2.25 (s, 3H), 2.17 (d. ./ 1.76 Hz, 2H), 1.22 (br. s.,2H), 1.09 (dd, J = 7.72, 3.31Hz, 2H). HPLC: Retention Time: 2.87 min. MS: (M+lT) m/z. 395.2. 5-(4-((4-cyclopropyl-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3-methyl-lH-pyrazol-l-yl)-l- methylpiperidin-2-one (A-27): MR (400 MHz, CDC13): delta 8.43 (s, IH), 7.86 (br, s,, IH), 6,49 – 6.87 (m, IH), 4.56 id. ./ 6.62 Hz, IH), 3.71 (d, ./ 7.06 Hz, 21 1 ). 3.00 (s, 3H), 2.48 – 2.64 (m, 2H), 2.34 – 2.45 (m, IH), 2.17 ·· 2.34 (m, 4H), 1.22 – 1.30 (m, 21 1 ). 1.15 (br. s., 2H). HPLC: Retention Time: 2.86 m in. MS: ( M l ) m/z: 395.2.

Statistics shows that 3-Methyl-4-nitro-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 5334-39-4.

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); 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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Formula: C5H6N2O

Step 2:, I-methyl -IH-pyrazole-4-carbaldehyde oxirne VA mixture Of the combined organic layer having l-methyl-IH-pyrazole-4-carbaldehyde and ethyl acetate obtained from step I and hydroxylamine hydrochloride (63.48gm, 0.9135 moles) was refluxed at 70-80C for 2-4 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 0-5C, to this added DM water (100 ml) and 25% aqueous ammonia solution (100 ml) at 0-5C. The reaction mixture was stirred for 10 mm at 20-30C. The organic layer was separated and aqueous layer was extracted withethyl acetate (250 ml). The entire organic layer was transferred to the reaction vessel and washed with 10% brine solution (500 ml). Stirred for 10 mm and separated the final aqueouslayr and organic layer. The organic layer was evaporated to obtain the l-methyl-lHpyrazole-4-carbaldehyde oxime.Drywt V : 60gmYield :1.2w/w(79%)HPLC purity : 99.78%

The synthetic route of 25016-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RALLIS INDIA LIMITED; PALIMKAR, Sanjay Sambhajirao; PAWAR, Jivan Dhanraj; SANKAR, B; KADAM, Subhash Rajaram; HINDUPUR, Rama Mohan; PRABHU, Venkatesh M; PATI, Hari Narayan; SUPHALA, Vadiraj Gopinath; MANE, Avinash Sheshrao; WO2014/2110; (2014); 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. 400877-57-8, name is Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H7N3O4

10% palladium/C (2.87 g, 2.7 mmol) was added to a stirred solution of methyl 1-methyl- 4-nitro-1 H-pyrazole-3-carboxylate (p129, 7.15 g, 38.6 mmol) in methanol (250 ml_) and stirred at RT under H2 atmosphere for 4 hrs. The catalyst was filtered off and the solvent was evaporated under vacuum to afford methyl 4-amino-1-methyl-1 H-pyrazole- 3-carboxylate (p130, 6 g, y= quant) as purple wax used as such in the next step. MS (/T7/z): 156.1 [MH]+.

According to the analysis of related databases, 400877-57-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; BERTANI, Barbara; GIBSON, Karl Richard; DI FABIO, Romano; RAVEGLIA, Luca; ZANALETTI, Riccardo; CREMONESI, Susanna; POZZAN, Alfonso; SEMERARO, Teresa; TARSI, Luca; LUKER, Timothy Jon; (275 pag.)WO2019/43407; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics