Day: August 17, 2021

Reference of 143426-52-2, 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 143426-52-2 as follows.

To a stirred solution of intermediate 1 (0.15 g, 0.73 mmol) in MeCN (10 mL), were added Intermediate 11 (0.14 g , 0.75 mmol) and trimethylamine (0.27 mL, 1.86 mmol ) at RT and the resulting mixture was stirred overnight at RT. After completion of reaction, the reaction mixture was quenched with water (10 mL) and extracted with EtOAc (3 x 30 ml_). The combined organic layer was washed with brine (30 mL), dried over Na2S04, filtered and concentrated under vacuum. The resulting crude material was purified by prep-HPLC (Method B) to get desired compound. Yield: 39% (90 mg, White solid). 1H NMR (400 MHz, DMSO-d6): d 8.45 (d, J = 2.0 Hz, 1 H), 7.77-7.73 (m, 3H), 7.35 (d, J = 8.4 Hz, 2H), 6.93-6.82 (m, 3H), 6.53 (s, 1 H), 4.22 (s, 4H), 3.72 (d, J = 13.2 Hz, 1 H), 3.33-3.27 (m, 1 H), 3.09-3.06 (m, 1 H), 2.97 (t, J = 7.6 Hz, 1 H), 2.19-2.06 (m, 2H), 1.81-1.71 (m, 2H), 1.70-1.56 (m, 1 H). LCMS: (Method A) 362.1 (M+H), Rt. 97.70 min, 88.96% (Max). HPLC: (Method A) Rt. 2.88 min, 97.88% (Max).

According to the analysis of related databases, 143426-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; WISHART, Grant; KULKARNI, Santosh S.; RAKESH, Paul; (338 pag.)WO2020/39027; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 637336-53-9, 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. 637336-53-9, name is Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 6-chloro-N-cyclopropyl-8-((4-methoxybenzyl)(methyl) amino)imidazo [1 ,2-bjpyridazine-3 -carboxamide (id) (125 mg, 0.324 mmol), methyl 4- amino-1-methyl-1H-pyrazole-3-carboxylate (101 mg, 0.648 mmol) [Free based (sodium bicarbonate solutionlEtOAc) from HC1 salt purchased from Art-Chem-BBj, Pd2(dba)3 (29.7 mg, 0.032 mmol), XANTPHOS (37.5 mg, 0.065 mmol) and C52CO3 (422 mg, 1.296mmol) in DMA (2 mL) was degassed by bubbling N2 through the mixture for 5 minutes. The reaction vessel was sealed and heated to 125 C for 8 hr. After cooling to rt, the reaction mixture was partitioned between EtOAc (30 ml) and water (20 ml). The organic layer was extracted with iN NaOH (10 ml) and the combined aqueous layers were washed with EtOAc (20 ml). The aqueous layer was acidified to pH 1 with iN HC1 andthe mixture was transfered to a separatory funnel and the aqueous layer was extracted with EtOAc (3 x 25 ml). The combined organic layers were washed with 10%LiC1 solution (2 x 50 ml) and brine (50 ml). After drying (Na2SO4) and filtration the organic layer was concentrated to afford 4-((3 -(cyclopropylcarbamoyl)-8-((4-methoxybenzyl)- (methyl)amino)imidazo [1 ,2-bj pyridazin-6-yl)amino)- 1-methyl- 1H-pyrazole-3 -carboxylicacid (le) (126 mg, 0.257 mmol, 79 % yield) as a tan solid. LC retention time 2.60 mm [Cj. MS (E+) m/z: 491 (MF-T)

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SPERGEL, Steven, H.; MERTZMAN, Michael, E.; (132 pag.)WO2018/67432; (2018); 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. 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H14N4O

General procedure: A mixture of 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide 1a (1.0 mmol), Ketones 2(1.0 mmol) and InCl3 (10 mol%,) in acetonitrile (6 mL) was stirred at room temperature for the time indicated in Table 3. After completion of the reaction (indicated by TLC) the reaction mixture was filtered and wash with acetonitrile (2 X 5 mL) to remove the insoluble catalyst. The filtrate was collected and concentrated under vacuum. The solid isolated was triturated with MTBE (10 mL), filtered and dried to give the desired product.

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; Ismail; Kuthati, Bhaskar; Thalari, Gangadhar; Bommarapu, Venkatesham; Mulakayala, Chaitanya; Chitta, Suresh Kumar; Mulakayala, Naveen; Bioorganic and Medicinal Chemistry Letters; vol. 27; 6; (2017); p. 1446 – 1450;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 52222-73-8, The chemical industry reduces the impact on the environment during synthesis 52222-73-8, name is 4-(Trifluoromethyl)-1H-pyrazole, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of compound 10 (500 mg, 1.03 mmol), 4-methylpyridin-2-ol (168 mg, 1.54 mmol) and K2CO3(283 mg, 2.05 mmol) in DMF (5 mL) was stirred at 80 oC for 10 hoursand then concentrated in vacuo to remove DMF. The residue was diluted withwater and extracted with EtOAc. The organic layer was washed with brine, driedover Na2SO4, filtered and concentrated in vacuo. Theresidue was purified by column chromatography (PE : EtOAc = 1 : 1) to give theproduct of 1r (400 mg, yield: 83%).

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-(Trifluoromethyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; He, Shuwen; Li, Peng; Dai, Xing; McComas, Casey C.; Du, Chunyan; Wang, Ping; Lai, Zhong; Liu, Hong; Yin, Jingjun; Bulger, Paul G.; Dang, Qun; Xiao, Dong; Zorn, Nicolas; Peng, Xuanjia; Nargund, Ravi P.; Palani, Anandan; Tetrahedron Letters; vol. 55; 14; (2014); p. 2212 – 2216;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 16617-46-2, 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. 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of compound SI (5.0 g, 46.30 mmol) and 2-bromo-l,l- diethoxyethane (10.0 g, 50.90 mmol) in DMF (20 mL) was added K2CO3 (12.78 g, 92.60 mmol) in one portion. The reaction mixture was stirred at 80 °C overnight. After cooling to room temperature, the mixture was poured into ice water and extracted with ethyl acetate (250 mL). The organic layer was washed with brine, dried over anhydrous Na2S04, filtered and then concentrated. The residue was purified by column chromatography on silica gel (petroleum ethenethyl acetate = 100: 1 to 5: 1) to afford compound S2 (9 g, yield 90percent) as a yellow oil.

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

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (447 pag.)WO2017/35408; (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. 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C14H22N4O4

General procedure: Cbz-Arg(N,N-diBoc)-Val-Sta-NH(CH2)2Ph (69). A mixture of Cbz-Orn(N-Boc)-Val-Sta-NH(CH2)2Ph (52) (65 mg, 0.090 mmol) and 4M HCl in dioxane was allowed to stir for 1 h at 20C. The reaction mixture was concentrated to dryness in vacuo to obtain the crude residue as a on oil. The oil was dissolved in DCM (1 mL) and Et3N (6 muL, 0.043 mmol) was added. The solution was stirred vigorously for 5min. N,N?-bis-Boc-1-guanylpyrazole (13 mg, 0.042 mmol) was added and the solution was allowed to stir for 18 h at 20C. The reaction mixture was concentrated to dryness in vacuo to obtain a crude residue. The crude residue was subjected to a silica chromatography gradient eluting from 100% DCM to 10% MeOH/DCM to obtain Cbz-Arg(N,N-diBoc)-Val-Sta-NH(CH2)2Ph (69) as a solid (46 mg, 53%).

According to the analysis of related databases, 152120-54-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nguyen, William; Hodder, Anthony N.; de Lezongard, Richard Bestel; Czabotar, Peter E.; Jarman, Kate E.; O’Neill, Matthew T.; Thompson, Jennifer K.; Jousset Sabroux, Helene; Cowman, Alan F.; Boddey, Justin A.; Sleebs, Brad E.; European Journal of Medicinal Chemistry; vol. 154; (2018); p. 182 – 198;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, 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. name: 1-Methyl-1H-pyrazol-5-amine

Methyl 1 -((3 -(((benzyloxy)carbonyl)amino)oxetan-3 -yl)methyl)-4-(2-chloro-5 – methylpyrimidin-4-yl)- 1 H-pyrrole-2-carboxylate (1.34 g, 2.85 mmol), 1-methyl-i Hpyrazol-5-amine (0.829 g, 8.54 mmol), CS2CO3 (2.3 18 g, 7.11 mmol) and 3rd Generation BrettPhos precatalyst (0.258 g, 0.28 mmol) in 1,4-dioxane (100 mL) was stirred under anatmosphere of nitrogen at 90 °C for 2 hours. The reaction mixture was poured into EtOAc (100 mL), washed with water (3 x 100 mL), the organic layer was dried over Na2SO4, filtered and evaporated to afford yellow oil. The crude product was purified by flash silica chromatography, elution gradient 0 to 5percent MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 1 -((3 -(((benzyloxy)carbonyl)amino)oxetan-3 -yl)methyl)-4-(5 -methyl-2-(( i-methyl-i H-pyrazol-5 -yl)amino)pyrimidin-4-yl)- 1 H-pyrrole2-carboxylate (1.07 g, 70.7 percent) as a white foam. m/z (ES+), [M+H]+ = 532.

The synthetic route of 1192-21-8 has been constantly updated, and we look forward to future research findings.

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

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. 1105039-93-7, name is 1-(4-Methoxybenzyl)-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-(4-Methoxybenzyl)-1H-pyrazole-4-carboxylic acid

To resin PL-TFP, 1 .4mmol/g, 150-300um (300 mg) was added a solution of 1 -(4- methoxybenzyl)-1 H-pyrazole-4-carboxylic acid (64 mg, 0.276 mmol) and 4-DMAP (20 mg, 0.164 mmol) in DCM (4 ml)/DMF (1 ml). After 10 min shaking at rt, Nu,Nu’- diisopropylcarbodiimide (0.172 ml, 1 .102 mmol) was added and the mixture was shaked at rt overnight. The resin (loaded with the activated ester) was filtered and washed with DMF (2ml), DCM (10 ml) and THF (10 ml). The wet resin was suspended in THF (3ml), then pipetted back to flask. A solution of the amine 5-chloro-1 H-indazol-3- yl)methanamine (50 mg, 0.275 mmol) and TEA (230 muIota_, 1 .653 mmol) in THF (2 ml) was added to the resin suspension and the mixture was shaked at rt for 4 days, filtered and washed with THF. The filtrate was diluted with EtOAc and washed with HCI 1 N, aq. sat. NaHC03 and brine. The organic layer was dried (Na2S04), filtered and concentrated. The residue was triturated with ACN (1 ml), the precipitate was filtered, washed with ACN (1 ml) and dried on HV.UPLC RtE= 0.85 min, [M+H]+ = 396.3-398.4, 1H NMR (400 MHz, DMSO-d6) delta ppm 3.71 (s, 3 H) 4.68 (d, 2 H) 5.23 (s, 2 H) 6.70 – 6.99 (m, 2 H) 7.10 – 7.26 (m, 2 H) 7.31 (dd, 1 H) 7.50 (d, 1 H) 7.81 – 7.93 (m, 2 H) 8.20 (s, 1 H) 8.65 (br. s., 1 H) 13.01 (s, 1 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 1105039-93-7.

Reference:
Patent; NOVARTIS AG; FLOHR, Stefanie; MARKERT, Christian; NAMOTO, Kenji; PIRARD, Bernard; WO2013/111108; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, 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. Application In Synthesis of 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide

General procedure: To a solution of 2-aminobenzamide (1.470 mmol, 1.0 eq.) was added to a solution of Terminal Alkyne (1.470 mmol, 1.0 eq.), Tosyl Azide, (1.470 mmol, 1.0eq.), CuI (0.147 mmol, 0.1 eq.), triethylamine (2.941 mmol, 2.0 eq.), in acetonitrile (10 ml) under N2 atmosphere. The mixture was stirred at room temperature for 12 h. After completion of the reaction (as indicated by TLC) the reaction mixture was poured into water (25 mL) and extracted with ethyl acetate (2×25 mL), dried over Na2SO4, concentrated under vacuum to get crude compound which was purified by column chromatography using a mixture of petroleum ether: ethyl acetate to give the desired product as a white solid.

The synthetic route of 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Srishyalam; Devanna; Basaveswara Rao; Mulakayala, Naveen; Tetrahedron Letters; vol. 58; 30; (2017); p. 2889 – 2892;,
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. 84547-84-2, name is 4-Bromo-1-methyl-1H-pyrazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H5BrN2O2

A mixture of 4-bromo-l-methyl-lH-pyrazole-5-carboxylic acid (5.0 g, 24.4 mmol) and BH3.THF (36.6 mL of a 1 M solution in THF, 36.6 mmol) in THF (50 mL) was stirred at 50 C for 2 days; at this point LCMS showed the completion of the reaction. The reaction was cooled to RT and cautiously quenched with aq. 1N F1C1 and stirred at RT for 1 h, after which the mixture was extracted with EtOAc (3 X 50 mL). The combined organic extracts were concentrated in vacuo. The residue was (0667) chromatographed (80 g S1O2; continuous gradient from 0% to 100% EtOAc in hexanes, 25 min) to give the title compound (3.60 g, 18.9 mmol, 77 % yield) as a white solid. LCMS, [M+H]+ = 193.0.

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 84547-84-2.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; CHENG, Peter Tai Wah; ZHANG, Hao; LI, Jun; FANG, Tianan; CORTE, James R.; (135 pag.)WO2019/126103; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics