Category: 5334-39-4

Synthetic Route of 5334-39-4, 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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 550 mg (2.45 mmol) 4-[(5-methyl-4-nitro-1 H-pyrazol-1 – yl)methyl]piperidine and 4-[(3-methyl-4-nitro-1 H-pyrazol-1 -yl)methyl]piperidine (intermediate 18B) in 5 mL DMF was stirred with 195 muL (2.06 mmol) ethanesulfonyl chloride and 1.23 mL (8.83 mmol) triethylamine overnight. Saturated aqueous sodium bicarbonate was added to the reaction. The mixture was extracted with ethyl acetate, and the combined organic phase was washed with brine, dried, filtered, and evaporated. 628 mg of the desired title compounds as crude product were obtained which were used without further purification. 1 H NMR (400 MHz, DMSO d6): delta (ppm) = 1.19 (t, 3H), 1.20 / 1.27 (m, 2H), 1.57 (m, 2H), 2.00 (m, 1 H), 2.42 / 2.62 (s, 3H), 2.76 (m, 2H), 3.01 (q, 2H), 3.58 (m, 2H), 4.03 / 4.09 (d, 2H), 8.80 / 8.24 (s, 1 H).

The chemical industry reduces the impact on the environment during synthesis 3-Methyl-4-nitro-1H-pyrazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHMANN, Bernd; HEISLER, Iring; MUeLLER, Thomas; CLEVE, Arwed; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (194 pag.)WO2016/12474; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 5334-39-4, 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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of PPh3 (4.28 g, 0.016 mole, 1.1 equiv) and DIAD (3.33 gm,, 0.016 mole, 1.1 equiv) in THF (2mL), was added 4-nitro-lH-pyrazole (1.96 g, 0.004 mmol, 1.0 equiv) The reaction mixture was added l-[2, 4-bis (trifluoromethyl) phenyl] ethanol (4 g, 0.004 mmol, 1.0 equiv). The reaction mixture was stirred at room temperature for 1 hrs. Product formation was confirmed with TLC and LCMS. After completion of reaction mixture were diluted with EtOAc (50 mL) and washed with water (3×50 mL). Organic layer dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain crude which was further purified by flash column chromatography to obtain pure product l-(l-(2,4- bis(trifluoromethyl)phenyl)ethyl)-5-methyl-4-nitro-lH-pyrazole (0.5 gm) and l-(l-(2,4- bis(trifluoromethyl)phenyl)ethyl)-3-methyl-4-nitro-lH-pyrazole (1.5 gm). LCMS: 368 [M+H] +.

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

Reference:
Patent; PRAXIS BIOTECH LLC; ALFARO, Jennifer; BELMAR, Sebastian; NUNEZ VASQUEZ, Gonzalo Esteban; PUJALA, Brahmam; SATHE, Balaji Dashrath; BERNALES, Sebastian; CHAKRAVARTY, Sarvajit; THAKRAL, Pooja; PATIDAR, Rajesh Kumar; (344 pag.)WO2019/195810; (2019); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, molecular formula is C4H5N3O2, 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: C4H5N3O2

General procedure: Compound 30-3 and 3-bromo-2-(bromomethyl)prop-l -ene are combined with K -CO . in DMF to give compound 47-1. Compound 47-1 is combined with lithium bis(trimethylsilyl)amide to give compound 47-2, Compound 47-2 is combined with NaB in MeOH to give compound 47-3, Compound 47-3 is combined with compound 1-1, PPh3, and DIAD in THF to give compound 47-4. To compound 47- 4 in MeOH is added Pd/C, and the mixture is stirred under H2 to produce compound 47-5. Compound 47- 5, compound 5-5, and TsOH are combined in 1 ,4-dioxane to give compound D-52

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5334-39-4, its application will become more common.

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

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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Methyl-4-nitro-1H-pyrazole

To a solution of cw-3-benzyloxycyclobutanol (17 g, 95 ,4 mmol) and 3-methyl-4-nitro-lH-pyrazole (12.1 g, 95.4 mmol) in THF (350 mL) was added PPh3 (37.5 g, 143 mmol). Then, DIAD (28.9 g, 143 mmol) was added slowly at 0 C, and the mixture was stirred at 15 C for 20 h. The mixture was quenched with H2Q (100 mL), then filtered. The filtrate was then extracted with EtOAc (3 x 70 mL), The organic phase was washed with brine (30 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by silica gel colum chromatography (PE:EtOAc = 10: 1 to 7: 1), to give trans- l-(3-benzyloxycyclobutyl)-5-methyl-4-nitro-pyrazole and trans-l-(3- benzyloxycyclobutyl)-3-methyl-4-nitro-pyrazoleTo a solution of /ra>v-l-(3-benzyloxycyclobutyl)-5-methyl-4-nitro-pyrazole and rra?is-l-(3-benzyloxyxyck)butyl)-3-methyl-4-nitro-pyrazole (19.5 g, 67.9 mmol) in DCM (200 mL) was added BC1 (1 M, 26.5 mL) at 0 C, and the mixture was stirred at 0 C for 2 h. The mixture was poured into water (200 mL) slowly, then extracted with DCM (2 x 100 mL). The organic phase was washed with aqueous ai K ()·. (50 mL), brine (40 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography (PE/EtOAc = 2 : 1 to 1 : 1), to give trans-3-[5- methyi-4-nitro-pyrazol- 1 -yl]cyclobutanol and rr s-3-[3-metiiyl-4-nitro-pyrazoi-l-yl]cyclobutanol as a mixture as a white soli d .

According to the analysis of related databases, 5334-39-4, the application of this compound in the production field has become more and more popular.

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

5334-39-4, name is 3-Methyl-4-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. Safety of 3-Methyl-4-nitro-1H-pyrazole

DIAD (930 muIota_, 4.7 mmol) was added to a solution of 3-methyl-4-nitro-1 H-pyrazole (500 mg, 3.93 mmol), /V-methyl-4-piperidinol (453 mg, 3.93 mmol) and triphenylphosphine (1238 mg, 4.7 mmol) in THF (25ml_). The reaction mixture was stirred at rt for 5 days. The mixture was cone, in vacuo before purification by flash chromatography on silica, washing with 50% EtOAc/DCM, followed by 5/45/50 MeOH/EtOAc/DCM mixture. The product was eluted with 2/5/43/50 NEt3/MeOH/EtOAc/DCM mixture to give the title compound as an off-white low melting solid (202 mg, 23%). LCMS (Method 1 ) Rt 2.7 min, ESIMS m/z [M+H]+ 225.3.

The synthetic route of 5334-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIONOMICS LIMITED; HARVEY, Andrew John; RIPPER, Justin Anthony; HUFF, Belinda Cheryl; PAUL, Dharam; WO2015/123722; (2015); 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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C4H5N3O2

A suspension of 3-methyl-l-(4-(methylsulfonyl)phenyl)-4-nitro-lH-pyrazole compound and 5-methyl-l-(4-(methylsulfonyl)phenyl)-4-nitro-lH-pyrazole (0.57 g, 2.0 mmol) and palladium on carbon (10 wt%, 0.2 g) in ethanol was stirred under a hydrogen atmosphere at 55 C for 18 hours. The reaction mixture was filtered through celite and concentrated to give the title compounds as a mixture of regioisomers (446 mg, 87%).

The synthetic route of 5334-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAKER-GLENN, Charles; BURDICK, Daniel Jon; CHAMBERS, Mark; CHEN, Huifen; ESTRADA, Anthony; SWEENEY, Zachary Kevin; CHAN, Bryan K.; WO2012/62783; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5334-39-4, name is 3-Methyl-4-nitro-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 5334-39-4, Computed Properties of C4H5N3O2

: To a solution of l-ethyi-5-hydroxy-piperidin-2-one (530 mg, 3.70 mmol), 3-methyl-4-nitro-lH-pyrazole (706 mg, 5.55 mmol) and PPrn (i ,46 g, 5.55 mmol) in THF (20 mL) was added dropwise DIAD (1.12 g, 5.55 mmol ) at 0 C over 20 min. After addition, the mixture was stirred at this temperature for 40 min, and then the resulting mixture was stirred at 20 C for 1 1 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:EtOAc = 5: 1 to 0: 1) to give a mixture of l-ethyl-5-(5-methyl-4-nitro-lH-pyrazol-l- yi)piperidin-2~one and l~ethyl-5-(3~methyl-4-nitro-lH~pyrazol-l~yl)piperidin~2-one as a yellow solid. LCMS: RT 0.881 min, m/z = 253.1 [M+H]+ To a solution of l-ethyl-5-(5-methyl-4-nitro-pyrazol-l- yl)piperidin-2-one and l -ethyl-5-(3-metliyl-4-nitro-pyrazol-l-yl)piperidin-2-one (420 mg, 1.66 mmol) in MeOH (40 ml.) was added Pd/C (10%, 176 mg) under 2. The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 (15 psi) at 20 C for 2 h. The reaction mixture was filtered and the filtrate was concentrated to give a mixture of 5-(4-amino-5-methyl-lH- pyrazol-l-yl)-l-ethylpiperidin-2-one and 5-(4-atnino-3-methyl-lH-pyrazol-l-yl)-l-ethylpiperidin-2-one as a brown oil , LCMS: RT 0.566 min, m/z = 223 ,3 [M+Hf. To a solution of 5-(4-amino–5-methyi-pyrazoi-1–yl)-i -ethyl-piperidin-2.-one and 5-(4-arnino-3-rnetlwi-pyrazoi- I -yl)- I .-ethyl-piperidin.-2-one (310 rng, 1.39 mmoi), and 4-cyciopropvi-2-(methyisuifonyi)-5-(trifiuoromethyi)pyrimidine (370 mg, 1.39 mmoi)in 1,4-dioxane (10 mL) was added TFA (317mg, 2.78 mmol). The mixture was stirred at 100 c for 2 h. The reaction mixture was diluted with H,O (30 mL), adjusted with aq. NaHCO3 (30 mU) to pH 8 and extracted with EtOAc (3 x 30 mE). The combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give crude product. The crude product was triiurated with DMF (5 mE). The undissoived solid was filtered to givecrude product as a solid. This ciude product was separated by SFC to give 5-(4-((4-cyclopropyl–5- (trfiuoroniethyl)pyriniidin-2-yl)arnino)-3-methyl- 1H-pyrazoi- 1 -yl)- I -ethylpiperidin-2-one as a single enantiomer (Peak I in SFC) and 5-(4-((-cyciopropvi-5-(trifiuoromethyi)pvrimidin-2-yi)amino)-3- methyl-I H-pyrazol-1 -yi)-I -ethyipiperidin-2-one as a single enantiomer (Peak 2 in SFC). The DMF filtrate was concentrated to give crude product. This crude product was puiified by prep-HPLC TFA) and thentwice of SFC to give 5-(4-((-cyclopropyI-5-(tf1uoroinethyl)pyriinidin-2-yi)arnino)-5-metliyI- 1H- pyrazoi-i-yi)-i-cthyipiperidin-2-one as a single enantiomer (Peak 1 in SFC) and 5-(4–((4-cyciopropyi-5- (trifiuoroniethyl)pyrimidin-2-yi)amino)-5–mcthyi- I H-pyrazoi- 1 -yl)- I -ethyipiperidin-2-one as a single enantiomer (Peak 2 in SFC).First eluting isomer (Peak 1): (S)-5-(4-((4-cyclopropyl-5-(trifluoromethyl)pyrimidin-2-yI)ainino)-5-inethyl-IH-pyrazol4-yl)-1-ethylpiperidin-2-one (4-59): 1H NMR (400 MHz, MD3OD): dppm 8.25 – 8-45 (m. 1 H), 748 – 767 (m, I H), 4.64 4.79 (in, I H), 3.72 – 3.8-4 (in. 1 H), 356 – 363 (m,1 H), 344 – 354 (m, 1 H), 3.35 – 3.43 (in, I H), 2.50-2.61 (m, 2 H), 232 -244 (rn, I H), 2.25 (s, 3 H),2.09 -2.21 (in, 2 H), 0.98 1.34 (in, 7 H). HPLC: RT 2.480 miii. MS: m: 409.2 FM-f-Hi?. SFC: RT 5.72mm, == 100%.Second ehiting isomer (Peak 2): 5-(4-((4-cyclopropyl-5-(trifluoromethyi)pyrimidin-2-y)amino)-5-methy1-1H-pyrazoi-1-yl)-1-ethypiperidin-2-one (A-60): 1H NMR (400 MHz, CD3OD): dppm 8.21 – 8.48 (in, 1 H), 743 – 7.71 (in, I H), 4.67 – 4.80 (in, I H), 3.72 – 3.83 (in, I H), 356 – 362 (in,I H), 344 – 3.54 (in, 1 H), 3.34 – 3.43 (in, I H), 2.49 – 2.60 (in, 2 H), 233 – 244 (in, I H), 2.25 (s, 3 H),2.08 -2.21 (in, 2 H), 0.97- 1.34 (rn, 7 H). HPEC: RT 2.487 mm. MS; m/z; 409.1 [M+Hf. SFC: RT 6.33mm, cc = 100%.First eiuting isomer (Peak 1): 5-(4-((4-cyclopropvI-5-(trif1uoromethy)pvrimidin-2- yI)arnino)-3-rnethyl-1H-pyrazol-1-yl)-1.-ethylpiperidin-2-one (4-61): ?H NMR (400 MHz, CD3OD): oe ppm 8.34-8.43 (in, I H), 7.84 – 7.94 (in. I H), 4.54 -469 in, 1 H), 369 -3.79 (in, 2 H), 3.38-3.52 (in,2 H), 2.46- 2.57 (m. 2 H). 2.32-243 (m, 1 H). 2.22-2.30 (m, I H), 2.19 (s. 4 H). 1.18 – 131 (m, 2 H).1.07 – 1.17 (m, 5 Fl). FIPLC: RT 2.468 miii. MS: ith: 409.1 [M+Tlj. SFC: RT 4.87 miii, cc 100%. Second eluting isomer (Peak 2) :5-(4-((4-cyclopropyl-5-(trifluoromethyl)pyriinidin-2-yI)arnino)-3-rnethyi-1H-pyrazol-1-yI)-l -ethylpiperidin-2-one (A-62): ?H NMR (400 MHz, CD3OD): oeppm 8.34 – 8.42 (m, I H), 7.83 – 7.).S (m. I H). 4.56 – 471 (m, I H). 3.68 – 3.80 (m, 2 H), 3.37 – 3.53 (m.2 Fl). 2.45 – 2.58 (in, 2 H), 2.32- 2.43 (m, I H), 2.23 -2.30 (in, 1 Fl). 2.19 (s, 4 H), 1.19- 1.30 (m, 2 H),1.06 – 1.18 (in, 5 H). HPLC: RT 2.464 mm. MS: rn/i?: 40g. I [M+Hf. SFC: Rf 5.67 mm, cc 98.02%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyl-4-nitro-1H-pyrazole, and friends who are interested can also refer to it.

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

Reference of 5334-39-4, 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 5334-39-4 as follows.

To a solution of 245 mg (1.19 mmol) of a mixture of 1 -(4-fluorobenzyl)-5-methyl-1 H- pyrazol-4-amine and 1 -(4-fluorobenzyl)-3-methyl-1 H-pyrazol-4-amine (intermediate 1C) in 4.0 mL DMSO was added 453 mg (1.19 mmol) HATU, 0.26 mL N,N- diisopropylethylamine and 200 mg (0.99 mmol) commercially available 2,6- dimethylquinoline-4-carboxylic acid. The reaction mixture was stirred for 20 hours at 25 C. This mixture was directly purified via preparative HPLC (method A1 ) to obtain 92 mg (23%) of the desired title compound together with 208 mg (51%) of the regioisomer N-[1 -(4-fluorobenzyl)-3-methyl-1 H-pyrazol-4-yl]-2,6-dimethylquinoline-4- carboxamide. 1 H NMR (500 MHz, DMSO d6): delta (ppm) = 2.22 (s, 3H), 2.48 (s, 3H), 2.68 (s, 3H), 5.31 (s, 2H), 7.16 – 7.26 (m, 4H), 7.53 (s, 1 H), 7.60 (dd, 1 H), 7.79 (s, 1 H), 7.85 (s, 1 H), 7.89 (d, 1 H), 10.12 (s, 1 H).

According to the analysis of related databases, 5334-39-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHMANN, Bernd; HEISLER, Iring; MUeLLER, Thomas; CLEVE, Arwed; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (194 pag.)WO2016/12474; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 5334-39-4, 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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 3-methyl-4-nitro-lH-pyrazole (1 -1, 398 nig, 3.13 mmol) in DMF (10 niL) was added NaH (125 mg, 3.13 mmol, 60% purity) at 0 C, then the reaction was stirred at 20 C for 1 h. Then, (3-methyl- 5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyridin-6-yl) methanesulfonate (604 mg, 2.61 mmol, 70% purity) in DMF (4 mL) was added to the solution at 20 C. Then, the mixture was stirred at 80 C for 12 h. The reaction solution was added with NH4Q solution (20 ml,), extracted with DCM:MeOH (20 mL chi 3, ratio=3: l). The organic layers were combined, dried over Na2S04, filtered and concentrated under reduced pressure. The crude product was purified by prep-TLC (DCM:MeOH = 5: 1) to give a mixture of 3-niethy3~6~(3-methyi-4~nitro^ and 3- methyl-6-(5~methyl-4-nitro-pyra^ as a yellow gum. LCMS: RT 0.925 min, m/z = 263.1 | M – H j ‘ . NMR (400 MHz, CDC13): delta 8.25 (s, 0.6 H), 8.13 (s, 0.3 H), 4.68 – 4.81 (m, 1 H), 4.14 – 4.42 (m, 2 H), 3.02 – 3.31 (m, 2 H), 2.77 (s, 1 H), 2.55 (s, 2 H), 2.44 – 2.53 (m, 4 H), 2.43 (s, 1 1H 1).

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

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

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 5334-39-4 as follows. name: 3-Methyl-4-nitro-1H-pyrazole

In analogy to example 6-2, 98.2 mg (0.46 mmol) of a mixture of 4-[(4-amino-3- methyl-1H-pyrazol-1-yl)methyl]benzonitrile and 4-[(4-amino-5-methyl-1H-pyrazol-1- yl)methyl]benzonitrile (intermediate 17C-2 and 18C-2) and 102 mg (0.39 mmol) 6- methyl-2-phenylquinoline-4-carboxylic acid ([CAS-No. 60538-98-9], commercially available at e.g. Enamine, Chemical Diversity Labs, Matrix, Zerenex), were reacted to give after purification using a Biotage chromatography system (25 g snap KP-Sil column, hexane / 50- 100% ethyl acetate, then ethyl acetate / 0- 100% methanol) followed by a separation and purification via preparative HPLC (method 6a) 121 mg (67% yield) of the desired example 41 and 16 mg (9.0% yield) of the desired example 42-2. N-[1-(4-cyanobenzyl)-3-methyl-1H-pyrazol-4-yl]-6-methyl-2-phenylquinoline-4- carboxamide, example 41-2: 1H-NMR (400 MHz, DMSO d6) delta (ppm) = 2.21 (s, 3H), 2.52 (s, 3H), 5.41 (s, 2H), 7.44 (d, 2H), 7.49 – 7.61 (m, 3H), 7.68 (dd, 1H), 7.85 (d, 2H), 7.90 (s, 1H), 8.06 (d, 1H), 8.23 (s, 1H), 8.30 – 8.34 (m, 3H), 8.36 (s, 1H), 10.34 (s, 1H). N-[1-(4-cyanobenzyl)-5-methyl-1H-pyrazol-4-yl]-6-methyl-2-phenylquinoline-4- carboxamide, example 42-2: 1H-NMR (400 MHz, DMSO d6) delta (ppm) = 2.24 (s, 3H), 2.53 (s, 3H), 5.47 (s, 2H), 7.32 (d, 2H), 7.50 – 7.62 (m, 3H), 7.69 (dd, 1H), 7.84 – 7.88 (m, 2H), 7.89 (s, 1H), 7.96 (s, 1H), 8.06 (d, 1H), 8.26 (s, 1H), 8.31 – 8.36 (m, 2H), 10.27 (s, 1H).

According to the analysis of related databases, 5334-39-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; BUCHMANN, Bernd; CLEVE, Arwed; SIEBENEICHER, Holger; KOPPITZ, Marcus; SCHNEIDER, Dirk; BAUSER, Marcus; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (482 pag.)WO2016/202898; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics