Day: August 12, 2021

Adding a certain compound to certain chemical reactions, such as: 78208-72-7, name is Ethyl 3-isopropyl-1H-pyrazole-5-carboxylate, 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 78208-72-7, Formula: C9H14N2O2

Preparation 14 5-ISOPROPYL-1-R2- (TETRAHVDRO-PVRAN-2-YLOXV)-ETHYLL-1 H-PYRAZOLE-3-CARBOXYLID ethyl ester The ester of preparation 6 (509mg, 2. 8MMOL), 2- (2-bromoethoxy) tetrahydro-2H- pyran (732mg, 3. 5MMOL) and potassium carbonate (483mg, 3. 5MMOL) were dissolved in 1-methyl-2-pyrrolidinone (5mL) and the reaction mixture heated to 80°C for 18 hours. The reaction mixture was cooled, poured into ethyl acetate, washed with water (x 2) and brine, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with pentane: ethyl acetate 80: 20 to 60: 40 to yield the title product, 663mg (76percent). HNMR (CD3, 400MHZ) : 1.25 (d, 6H), 1.37 (t, 3H), 1.44-1. 71 (m, 6H), 2.97 (m, 1 H), 3.42 (m, 1 H), 3.54 (m, 1 H), 3.75 (m, 1 H), 4.00 (m, 1 H), 4.32 (m, 2H), 4.54 (t, 1 H), 4.68 (m, 1 H), 4.76 (m, 1 H), 6.64 (s, 1 H). MS ES+ M/Z 227 [MH] +

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 LIMITED; PFIZER INC.; WO2005/9965; (2005); 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. 72760-85-1, name is 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 72760-85-1

General procedure: A mixture of pyrazole-imines 7 (1 mmol), aldehyde (1 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 8.

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; 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

These common heterocyclic compound, 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic acid, 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 1H-Pyrazole-3,5-dicarboxylic acid

1H-Pyrazole-3,5-dicarboxylic acid (200 mg, 1.281 mmol), methanamine (2M in THF, 0.705 mL, 1.409 mmol) and HATU (536 mg, 1.409 mmol) were combined in DMF (2 mL). DIPEA (0.448 mL, 2.56 mmol) was added and reaction mixture stirred at rt. under N2 for 2 h. The reaction mixture was concentrated to dryness and used crude for the next step. (0432) LCMS (2 min Formic): Rt = 0.37 min, [MH]+ = 183.1.

The synthetic route of 1H-Pyrazole-3,5-dicarboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LIWICKI, Gemma Michele; LUCAS, Simon Christopher Cranko; PRESTON, Alexander G; SEAL, Jonathan, Thomas; WALL, Ian David; WATSON, Robert J; (0 pag.)WO2018/158212; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1120-82-7, 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 1120-82-7 as follows.

first,4-bromobenzenamine (3.44 g,0.0200 mol) was dissolved in a CH2Cl2 solvent (30.0 mL). 1H-1-pyrazolyl-1-methanol (3.92 g, 0.0400 mol) was dissolved in a CH2Cl2 solvent (20.0 mL) and added. The reaction was carried out at room temperature for 24 hours, the water was removed by solution reaction with MgSO4,The solution was removed by pressure. A green solid was obtained after distillation under reduced pressure. (5.89 g, 88.7%).

According to the analysis of related databases, 1120-82-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kyungpook National University Industry-Academic Cooperation Foundation.; Lee, Hyo Sun; Jung, Jong Hwa; Choe, Sung Hey; Cho, Jae Won; (24 pag.)KR2017/51867; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 59843-75-3, name is 3-(p-Tolyl)-1H-pyrazole, molecular formula is C10H10N2, 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. Product Details of 59843-75-3

Production Example 143 3-p-Tolyl-1-trityl-1H-pyrazole 6.94 g of the title compound was obtained as pale brown crystals from 4.59 g 3-p-tolyl-1H-pyrazole (compound in Production Example 126) by the same method as in Production Example 15.1H-NMR (CDCl3) delta: 2.35(s, 3H), 6.50(d, J=2.4Hz, 1H), 7.16(d, J=8.0Hz, 2H), 7.21(m, 6H), 7.27 (d, J=2. 4Hz, 1H), 7.30(m, 9H), 7.69(d, J=8.0Hz, 2H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59843-75-3, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; EP1382603; (2004); 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. 138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 138786-86-4

PART I: Synthesis Scheme I, shows that 4-nitro-1H-pyrazole-3-carboxylic acid (compound 12) was alkylated with methyl iodide in the presence of potassium carbonate in DMF. After flash chromatography on silica gel, two regioisomers, alkyl 1-alkyl-4-nitro-1H-pyrazole-3-carboxylate (compound 13a, 1,3-isomer) and alkyl 1-alkyl-4-nitro-1H-pyrazole-5-carboxylate (compound 13b, 1,5-isomer) were obtained in 26% and 74% yield, respectively. The structures of the isomers (compounds 13a, 13b) were determined by NOESY analysis: a NOESY correlation was observed between H-5 and alkyl protons in compound 13a.16 The nitro group of compounds 13a and 13b was reduced by hydrogenation in the presence of a catalytic amount of catalytic amount of 10% Pd/C to produce amines compounds 14a and 14b, respectively. Cyclization of compound 14b with urea afforded compound 15. Chlorination of compound 15 with POCl3 and DIPEA in toluene afforded compound 16 in 68% yield. Treatment with appropriate substituted anilines in isopropanol with 1 drop of conc. HCl with compound 16, provided the instant compounds 4-11 of this invention (65-78% yields).

The synthetic route of 138786-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Duquesne University of the Holy Spirit; Gangjee, Aleem; (26 pag.)US2019/276457; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1202993-11-0, 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. 1202993-11-0, name is 5-Chloro-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.

Synthesis of 5-chloro-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carbonyl chloride (example Vc-1); 3.2 g of 5-chloro-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxylic acid and 44.3 ml of thionyl chloride were refluxed for 5 hours. After cooling down, the reaction mixture was evaporated under vacuum to yield 3.5 g of 5-chloro-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carbonyl chloride as a yellow oil.¾ NMR (400 MHz, CHC13- 6) delta ppm : 3.97 (s, 3H); 7.00 (t, J= 52.01 Hz, 1 H); IR (TQ) : 1759 and 1725 om C=0);

The synthetic route of 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; GREUL, Joerg; BENTING, Juergen; DAHMEN, Peter; WACHENDORFF-NEUMANN, Ulrike; WO2012/65932; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1227611-94-0,Some common heterocyclic compound, 1227611-94-0, name is 4-(4-Iodo-1H-pyrazol-1-yl)cyclohexanone, molecular formula is C9H11IN2O, 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.

Example 89: 4-(4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5- yl}-pyrazol-1-yl)cyclohexanone[428] A 20 ml sealable vial was charged with 3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-5- (4,4,5,5-tetramethyl[1 ,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (80.0 mg, 0.156 mmol), 4-(4-lodopyrazol-1-yl)cyclohexanone (52.5 mg, 0.172 mmol), Pd(PPh3)4 (12.0 mg, 0.0103 mmol), potassium carbonate (71.8 mg, 0.514 mmol), and 4:1 dioxane:water (5 mL). The cap was sealed and the vial was evacuated and backfilled with nitrogen (3x). After that, the vial was heated at 90 C for 2 h. The reaction mixture was partitioned between EtOAc/H2O (15 ml/10 ml). The aqueous phase was extracted with EtOAc (10 ml). The combined organic extracts were washed with water (10 ml) and brine (10 ml), dried over MgSO4, filtered, and concentrated in vacuo to give a brown oil that was purified by prep. TLC eluting with 4% MeOH/DCM to give the title compound. 1H NMR (400 MHz, CDCI3 ): delta = 1.88 (d, J = 7.2 Hz, 3 H), 2.31-2.68 (m, 8 H), 4.64 (tt, J = 1 1.8, 4.0 Hz, 1 H), 5.28 (q, J = 7.2 Hz, 1 H), 7.01 (dd, J = 8.0 & 8.8 Hz, 1 H), 7.30 (s, 1 H), 7.32 (brs, 1 H), 7.48 (s, 1 H), 7.60 (d, J = 0.8 Hz, 1 H), 7.66 (d, J = 0.8 Hz, 1 H), 8.41 (brs, 1 H), 9.77 (brs, 1 H). MS(ES+): m/z = 471.16/473.11 (100/68) [MH+]. HPLC: tR = 3.39 min (polar_5 min, ZQ3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Iodo-1H-pyrazol-1-yl)cyclohexanone, its application will become more common.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; CHEN, Xin; JIN, Meizhong; KLEINBERG, Andrew; LI, An-hu; MULVIHILL, Mark, J.; STEINIG, Arno, G.; WANG, Jing; WO2010/59771; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1031351-95-7, 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. 1031351-95-7, name is Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 3-formyl-l-methyl-lH-pyrazole-5-carboxylate (Bellen Chem;l g, 5.95 mmol) in CH2CI2 (30 mL) at 0 C was added bis-(2-methoxyethyl)aminosulfur-trifluoride (3.29 mL, 17.8 mmol) in CH2CI2 (5 mL) dropwise via syringe pump over 40 minutes. The mixture was allowed to stir at 0 C for 20 minutes, then the ice-bath was removed, and the mixture was allowed to warm to ambient temperature. The mixture was then allowed to stir for an additional 90 minutes and was quenched by slow addition of saturated, aqueous NaHC( (25 mL) added via syringe pump over 1 hour. The mixture was diluted with CH2CI2 (15 mL), then the layers were separated, and the aqueous layer was extracted with CH2CI2 (3 x 7 mL). The combined organic fractions were dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure. The residue was purified via column chromatography (S1O2, 50% ethyl acetate/heptanes) to give the title compound (1.01 g, 5.31 mmol, 89% yield). MS (ESI+) m/z 191 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1018446-95-1, name is tert-Butyl 4-amino-1H-pyrazole-1-carboxylate, 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 1018446-95-1, Safety of tert-Butyl 4-amino-1H-pyrazole-1-carboxylate

[0607j To a solution of N-(4-(2-chloropyrimidin-4-yl)-2-methylbenzyl)-3 – isopropoxyazetidine-1-carboxamide (220 mg, 0.60 mmol) and tert-butyl 4-amino-1H-pyrazole- 1-carboxylate (132 mg, 0.72 m mol) in dry 1,4-dioxane (8 mL) was added Pd2(dba)3 (55 mg,0.06 mmol), S-phos (49 mg, 0.12 mmol) and Cs2CO3 (390 mg, 1.2 mmol). The mixture was stirred at 120 C for 4 h under N2. After cooling to rt, the mixture was diluted with EtOAc (150 mL) and washed with water (60 mL x 2). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was dissolved in 3 N HC1 in MeOH (10 mL) and the resulting mixture was stirred at rt for 1 h. After concentration in vacuo, the residue was purified by prepHPLC (CH3CN/H20 with 0.05% NH4OH as mobile phase) to give N-(4-(2-((1H-pyrazol-4- yl)amino)pyrimidin-4-yl)-2-methylbenzyl)-3 -isopropoxyazetidine- 1 -carboxamide as a white solid (88 mg, yield: 35%). ESI-MS (M+H) : 544.2. ?H NMR (400 MHz, CD3OD) 5: 8.38 (d, J= 4.8 Hz, 1H), 8.05 (s, 1H), 7.91-7.90 (m, 2H), 7.75 (s, 1H), 7.37 (d, J= 8.4 Hz, 1H), 7.16 (d, J5.2 Hz, 1H), 4.42-4.36 (m, 3H), 4.18-4.14 (m, 2H), 3.81-3.78 (m, 2H), 3.67-3.61 (m, 1H), 2.41 (s, 3H), 1.14 (d, J 6.0 Hz, 6H).

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, tert-Butyl 4-amino-1H-pyrazole-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics