Day: July 6, 2021

Electric Literature of 67-51-6, These common heterocyclic compound, 67-51-6, name is 3,5-Dimethyl-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.

In a 250 ml reaction vessel, 3,5-dimethyl-1 H-pyrazole x51 (0.5 g, 5 mmol), I2 (0.79 g, 30 mmol) and CAN (1.71 g, 3 mmol) are dissolved in 70 ml of CH3CN and stirred at room temperature for 16 h. The solvent is evaporated, the residue dissolved in AcOEt and washed with a 10 % aqueous solution of Na2S2U3 and brine. The aqueous phase is re- extracted with AcOEt and the combined organic phases are dried over Na2SO4, filtered and concentrated to dryness to afford 1.15 g (100 %) of crude 4-iodo-3,5-dimethyl-1 H- pyrazole x52, which is used in the next step without further purification.LC-MS (MH+): 223.

Statistics shows that 3,5-Dimethyl-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 67-51-6.

Reference:
Patent; UCB S.A.; WO2006/128692; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 120068-79-3, 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. 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 1; Sulfinylation of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H- pyrazole-3-carbonitrile with triethylamine hydrochloride, sodium trifluoromethylsulfinate and thionylchloride, in 6.5 molar equivalents of tolueneWithin a 3-neck, 50 ml. round bottom flask equipped with a magnetic stirrer bar and a thermometer were placed vacuum dried sodium trifluoromethylsulfinate (4.29 g, 27.5 mmol), vacuum dried triethylamine hydrochloride (5.16 g, 37.5 mmol), and 13 ml. an- hydrous toluene (6.5 molar equivalents relative to 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H-pyrazole-3-carbonitrile) under an argon atmosphere. After cooling to 00C to 5 0C with an ice bath, thionylchloride (3.57 g, 30 mmol) was added slowly 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 (8.03 g, 25 mmol, 99 % purity) was added at 5 0C, and the reaction mixture was heated to 50 0C within 5 min by a preheated water bath. The temperature of 50 0C was kept for another 6 hours before quenching the reaction with 50 ml. of saturated NaHCO3 solution. The resulting suspension was diluted with 30 ml. of ethylacetate. After phase separa- tion the organic layer was washed once with saturated NaHCtheta3 solution and concentrated under reduced pressure until dryness. The crude product was crystallized from refluxing toluene (100 g) affording the title compound as a white crystalline powder (8.06 g, 70 % yield, 94 % purity by quantitative HPLC). 1H-NMR (Bruker DRX-500, d6- DMSO): delta [ppm]: 8.33 (s), 7.57 (s).; Example 3; Sulfinylation of 5-amino-1 -[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H- pyrazole-3-carbonitrile via addition of a mixture of sodium trifluoromethylsulfinate, triethylamine hydrochloride and thionylchloride to 5-amino-1-[2,6-dichloro-4- (trifluoromethyl)phenyl]-1 H-pyrazole-3-carbonitrileWithin a 3-neck, 50 ml. round bottom flask equipped with a magnetic stirrer bar and a thermometer were placed vacuum dried sodium trifluoromethylsulfinate (4.29 g, 27.5 mmol), vacuum dried triethylamine hydrochloride (5.16 g, 37.5 mmol), and 10 g anhydrous toluene under an argon atmosphere. After cooling to 0 – 5 0C with an ice bath thionylchloride (3.57 g, 30 mmol) was added while keeping the reaction temperature below 5 0C. After stirring for another 30 min the cooled sulfinic acid solution was added at once to a stirred suspension of vacuum dried 5-amino-1-(2,6-dichloro-4- trifluoromethyl-phenyl)-1 H-pyrazole-3-carbonitrile (8.03 g, 25 mmol, 99 % purity) in 5 g toluene with a temperature of 50 0C. The temperature of 50 0C was kept for another 5 hours before quenching the reaction with 50 ml. of saturated NaHCU3 solution. The resulting suspension was diluted with 30 ml. of ethylacetate. After phase separation the organic layer was washed once with saturated NaHCU3 solution and concentrated under reduced pressure until dryness. The crude product was crystallized from refluxing toluene (100 g) affording the title compound as a white crystalline powder (7.25 g, 63 % yield, 94 % purity by quantitative HPLC). 1H-NMR (Bruker DRX-500, d6- DMSO): delta [ppm]: 8.33 (s), 7.57 (s).; 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).; Example 15; Sulfinylation of 5-amino-1-[2,6…

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

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. 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1-Methyl-1H-pyrazole-5-carbaldehyde

Acetic acid (0.4 mL) was added to a solution of 2-methyl-2H-pyrazole-3-carbaldehyde (0.8 g) and 5-bromopyridine-2,3-diamine (1 g) in THF (20 mL) at room temperature. The mixture was stirred overnight at room temperature. The mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with water and a saturated brine, dried over magnesium sulfate, and then concentrated to obtain a residue. Sodium borohydride (300 mg) was added to a solution of the residue in THF (20 mL)/methanol (50 mL) at 0C, and the mixture was stirred for 1 hour. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was sequentially washed with water and a saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to obtain a pale yellow solid as 5-bromo-N3-((1-methyl-1H-pyrazol-5-yl)methyl)pyridine-2,3-diamine (0.38 g). A mixture of the obtained pale yellow solid (300 mg), acetic acid (0.1 mL), DMAP (10 mg), propylphosphonic anhydride (50% in ethyl acetate solution) (0.938 mL), DIPEA (0.464 mL) and THF (10 mL) was stirred under microwave irradiation at 200C for 2 hours. The mixture was purified by NH silica gel column chromatography (methanol/ethyl acetate) to obtain the title compound (188 mg). 1H NMR (300 MHz, DMSO-d6) delta 2.55 (3H, s), 3.81 (3H, s), 5.63 (2H, s), 5.70 (1H, d, J = 1.9 Hz), 7.30 (1H, d, J = 1.9 Hz), 8.24 (1H, d, J = 2.2 Hz), 8.42 (1H, d, J = 2.2 Hz).

The synthetic route of 27258-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KAWAKITA Youichi; KOJIMA Takuto; NII Noriyuki; ITO Yoshiteru; SAKAUCHI Nobuki; BANNO Hiroshi; LIU Xin; ONO Koji; IMAMURA Keisuke; IMAMURA Shinichi; (165 pag.)EP3450436; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 4522-35-4, 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. 4522-35-4, name is 3-Iodo-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

INTERMEDIATE 8 4-(3 -Iodo- lH-p yrazol- 1 – vPbenzonitrile To 3-iodo-lH-pyrazole (801 mg, 4.13 mmol) in DMSO (10 mL) at 0 C, was added sodium hydride (60% in mineral oil, 198 mg, 4.95 mmol). The reaction was warmed to 25 C and stirred for 60 min before methyl 4-fluorobenzonitrile (500 mg, 4.13 mmol) was added. The reaction mixture was stirred at 90 C for 4.5 h before quenching by the addition of water. The reaction mixture was extracted with EtOAc. The combined organic extracts were dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combifiash, 0-30% EtOAc in hexanes) to afford 4-(3-iodo-lH-pyrazol-l-yl)benzonitrile, as a pale yellow crystaline solid. LCMS calc. = 295.96; found = 295.90 (M+H)+. NMR (500 MHz, CDC13): delta 7.83 (m, 3 H); 7.78 (d, J= 8.5 Hz, 2 H), 6.71 (d, J= 2.6 Hz, 1 H).

The synthetic route of 3-Iodo-1H-pyrazole has been constantly updated, and we look forward to future research findings.

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; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); 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. 2075-46-9, name is 4-Nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., Formula: C3H3N3O2

General procedure: To a stirred solution of 4-nitroimidazole or 4-nitropyrazole (1.00 g, 8.84 mmol) in DMF (6.00 mL) at 25C were added K2CO3 (1.47 g, 10.6 mmol) and alkyl iodide(10.6 mmol). After stirring for 16 h at 25 C, the reactionmixture was treated with water (15 mL) and EtOAc (20 mL)and transferred to a 125 mL separatory funnel. The organiclayer was collected and the aqueous layer was extracted withEtOAc (25 mL × 2). The combined organic layers werewashed with brine (20 mL), dried over sodium sulfate andfiltered. The filtrate was concentrated, and the residue waspurified by flash column chromatography to provide thecorresponding alkyl azole.

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; Jung, Haeun; Bae, Seri; Jang, Ha-Lim; Joo, Jung Min; Bulletin of the Korean Chemical Society; vol. 35; 10; (2014); p. 3009 – 3014;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1453-58-3,Some common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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 3-methyl- 1H-pyrazole (500 mg) in acetonitrile (10 mL) were added di-tert-butyl dicarbonate (1.59 g, 1.7 mL) and DMAP (74.4 mg) at 0°C. The mixture was allowed to warm to rt and was stirred for 2 h. Then, EtOAc was added and the mixture was washed with 0.1 N HC1,saturated NaHCO3 solution and brine, dried with Na2504 and evaporated. The crude product(containing -15percent of tert-butyl 5-methylpyrazole-1-carboxylate) was used in the next reaction step without further purification.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HERT, Jerome; HUNZIKER, Daniel; KUEHNE, Holger; LUEBBERS, Thomas; MARTIN, Rainer E.; MATTEI, Patrizio; NEIDHART, Werner; RICHTER, Hans; RUDOLPH, Markus; PINARD, Emmanuel; (450 pag.)WO2017/37146; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 31108-57-3, 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 31108-57-3 as follows.

Synthesis of II-B14 To a solution of II-B13 (220 mg, 0.53 mmol) in acetone (3 mL) was added 4-cyano-pyrazole (197 mg, 2.1 mmol) and K2C03 (292 mg, 2.1 mmol). After stirring at 25C for 16 h, the reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2 x 10 mL). The combined organic solution was concentrated and purified by prep-HPLC (Instrument: BF; Column: Xtimate C18 l50*25mm*5pm; Condition: water (0.225% FA)-ACN; Begin B: 50; End B: 70; Gradient Time (min): 7.5; 100%B Hold Time (min): 2; FlowRate (mL/min): 30), lyophilized and re-crystallized from MeCN/H20 (20 mL, 1 : 1) to give II-B14 (84 mg, 37%) as a solid. 1H NMR (400 MHz, CDCl3) dH, 7.84-7.78 (m, 2H), 5.07 (d, 7= 18.0 Hz, 1H), 4.95 (d, 7 = 18.6 Hz, 1H), 3.88-3.77 (m, 2H), 3.71 (dd, 7=3.6, 11.6 Hz, 1H), 3.27 (t, 7= 11.6 Hz, 1H), 2.72 (dd, 7=3.6, 11.2 Hz, 1H), 1.89-1.69 (m, 5H), 1.55-1.24 (m, 15H), 1.16-0.99 (m, 6H); LC-ELSD/MS purity 99%, MS ESI calcd. for C25H34N302 [M+H-H20]+ 408.3, found 408.2.

According to the analysis of related databases, 31108-57-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAGE THERAPEUTICS, INC.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, G.; BLANCO-PILLADO, Maria, Jesus; LA, Daniel; HARRISON, Boyd, L.; (206 pag.)WO2019/140272; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 81945-73-5, 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. 81945-73-5, name is 1H-Pyrazol-1-ol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 27: Synthesis of 5-Bromo-l-(2,6-difluorobenzyl)-lH-pyrazoIeStep 1: 2-(2,6-Difluorobenzyl)-l-hydroxy-lH-pyrazole1-Hydroxypyrazole (49.3 mg, 0.59 mmol, 1.0 eq) was mixed with 165.8 mg (0.80 mmol, 1.36 eq) of 2,6-difluorobenzyl bromide in -1-2 mL of anhydrous CHCl3 under argon. The mixture was heated at 80 0C for 18 h under inert atmosphere in a sealed flask without condenser. The residue was partitioned between 37 weight percent aqueous HCl and toluene. The aqueous layer was collected and the toluene fraction extracted again with 37 weight percent aqueous HCl. The combined aqueous HCL fractions were neutralized with 5N aqueous NaOH to pH~l 1-12 and then back-extracted with 3 x 30 mL of CHCl3. The organic layers were combined, washed with brine, dried over Na2SO4 and concentrated under reduced pressure to yield 86.3 mg (70.1% yield) of 2-(2,6- difluorobenzyl)-l -hydroxy- lH-pyrazole as a tan brown solid. 1H NMR (CDCl3 300 MHz) delta 7.37 (m, IH), 7.18 (d, IH), 6.95 (t, 2H), 6.85 (d, IH), 6.11 (t, IH), 5.43 (s, 2.00 H). LC/MS (ES) M+l=211.2Step 2: 5-Bromo-l-(2,6-difluorobenzyl)-lH-pyrazole2-(2,6-Difluorobenzyl)-l -hydroxy- lH-pyrazole (81.2 mg, 0.386 mmol, l.Oeq) and 5ml of anhydrous CHCl3 were combined in a flame-dried 25 mL round-bottom flask under argon and cooled in an ice/water bath. A solution Of POBr3 (398.1 mg, 1.39 mmol, 3.60 eq) in 3 mL of CHCl3 was added using a syringe in aliquots over an hour period with stirring. The reaction solution was warmed to room temperature and stirred for 16 hours. The CHCl3 was removed in vacuo and the resulting orange mixture was neutralized with saturated aqueous NaHCO3 and extracted with 3 x 30 mL of diethyl ether. The combined ether fractions were washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 101.5 mg (96.7% yield) of 5 -bromo-1 -(2,6- difluorobenzyl)- lH-pyrazole as a hygroscopic orange-tan colored solid. 1H NMR (CDCl3 300 MHz) delta 7.51 (d, IH), 7.34 (m, IH), 6.94 (t, 2H), 6.29 (d, IH), 5.50 (s, 2H). LC/MS (ES) M+l= 273.1, 275.1

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

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2006/44528; (2006); 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 26308-42-9 as follows. category: pyrazoles-derivatives

Example 252 Production of N-{2-chloro-5-[(2-{[(2-methylcyclopropyl)carbonyl]amino}imidazo[1,2-b]pyridazin-6-yl)oxy]phenyl}-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide Using 3-ethyl-1-methyl-1H-pyrazole-5-carboxylic acid (181 mg, 1.17 mmol), tetrahydrofuran (4.5 mL), N,N-dimethylformamide (30 muL, 0.39 mmol), oxalyl chloride (102 muL, 1.17 mmol), N-[6-(3-amino-4-chlorophenoxy)imidazo[1,2-b]pyridazin-2-yl]-2-methylcyclopropanecarboxamide (300 mg, 0.84 mmol) and N,N-dimethylacetamide (6.0 mL), and in the same manner as in Example 249, the title compound (207 mg, 50%) was obtained as a white powder. 1H-NMR (DMSO-d6, 300 MHz) delta 0.61-0.73 (1H, m), 0.97-1.04 (1H, m), 1.05-1.09 (3H, m), 1.16-1.25 (1H, m), 1.19 (3H, t, J=7.5 Hz), 1.62-1.73 (1H, m), 2.55 (2H, q, J=7.5 Hz), 3.99 (3H, s), 6.88 (1H, s), 7.08 (1H, d, J=9.5 Hz), 7.21-7.27 (1H, m), 7.53 (1H, d, J=3.0 Hz), 7.62 (1H, d, J=8.7 Hz), 7.94 (1H, s), 8.05 (1H, d, J=9.5 Hz), 10.00 (1H, s), 10.99 (1H, s).

According to the analysis of related databases, 26308-42-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/137595; (2009); 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. 180207-57-2, name is 2-(1H-Pyrazol-4-yl)ethanol, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-(1H-Pyrazol-4-yl)ethanol

EXAMPLE 242 l-(5-(4-(2 -hydroxy ethyl)-lH-pyrazol-l-yl)-4-(isopropylamino)pyridin- -b]pyridine-5-carbonitrile In a 20 mL microwave vial, l-(5-iodo-4-(isopropylamino)pyridin-2-yl)-lH- pyrazolo[3,4-b]pyridine-5-carbonitrile (50 mg, 0.12 mmol), 2-(lH-pyrazol-4-yl)ethanol (13.9 mg, 0.12 mmol), potassium carbonate (51.3 mg, 0.37 mmol) and Nl,N2- dimethylethane-l,2-diamine (6.54 mg, 0.074 mmol) were mixed in 1,4-dioxane (1 mL) at room temperature with stirring. While bubbling in nitrogen, copper(I) iodide (4.71 mg, 0.025 mmol) was added and the mixture was capped and heated with stirring at 110 C for 5 hours. After cooling, the reaction mixture was filtered, and the filtrate was concentrated under high vacuum and the residue was dissolved in DMF for purification. The product was purified via preparative HPLC to afford l-(5-(4-(2-hydroxyethyl)-lH- pyrazol-l-yl)-4-(isopropylandno)pyridin-2-yl)-lH-pyrazolo[3,4-b]pyridine-5-carbonitrile (4.4 mg, 8% yield). NMR (500MHz, DMSO-de) delta 9.11-8.97 (m, 2H), 8.65 (br s, IH), 8.36 (br s, IH), 8.17 (s, IH), 7.77 (s, IH), 7.39 (br s, IH), 7.26 (d, J=7.3 Hz, IH), 4.76 (br s, IH), 3.84-3.74 (m, IH), 3.67-3.59 (m, 2H), 2.67 (t, J=6.9 Hz, 2H), 1.24 (d, J=6.2 Hz, 6H); LC/MS: 389.0 (M+H); HPLC rt 1.37 min, conditions C.

According to the analysis of related databases, 180207-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GARDNER, Daniel S.; SANTELLA, Joseph B.; PAIDI, Venkatram Reddy; WU, Hong; DUNCIA, John V.; NAIR, Satheesh Kesavan; HYNES, John; (300 pag.)WO2016/210034; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics