Day: July 27, 2021

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. 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, A new synthetic method of this compound is introduced below., Computed Properties of C7H7F3N2O2

To a stirred solution of (5-methyl-3-trifluoromethyl-pyrazol-l-yl)acetic acid (0.0885 g, 0.4255 mmol) in dichloromethane (10 mL) was added oxalylchloride (0.108 g, 0.851 mmol) and drop a of DMF. The reaction mixture was stirred at 45 C for 2 h, and then concentrated under reduced pressure to provide the title compound as a white solid (0.096 g)..H NMR (CDCI3): delta 6.38 (s, 1H), 5.27 (s, 2H), 2.31 (s, 3H).

The synthetic route of 345637-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; LIEPA, Andris, Juris; PASTERIS, Robert, James; STEVENSON, Thomas, Martin; WO2011/85170; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 27258-33-9,Some common heterocyclic compound, 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde, molecular formula is C5H6N2O, 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.

Compound 24; [6-(2-Methyl-2H-pyrazol-3-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl]-quinolin-3-yl- amine; [00404] A 1.5 mL vial was charged with a solution of (6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)- quinolin-3-yl-amine (6.0 mg, 0.023 mmol) and 2-methyl-2H-pyrazole-3-carbaldehyde (0.046 mmol) in dimethyl sulfoxide (150 uL, 2.1 mmol). A solution of sodium triacetoxyborohydride (14 mg, 0.068 mmol) and acetic acid (2.6 uL, 0.046 mmol) in dimethyl sulfoxide (150 uL, 2.1 mmol) was added and the mixture stirred at room temperature. Aliquot (3 uL) after 2 h showed complete conversion. The mixtures were purified by reverse-phase HPLC (25-80% ACN in 10 mM Et2NH/H2O) to afford the title compound.

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

Reference:
Patent; RENOVIS, INC.; DUNCTON, Matthew; O’MAHONY, Donogh, John, Roger; COX, Matthew; WO2010/59610; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 637336-53-9, 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 637336-53-9 as follows.

Isoamyl nitrite (1 .3 ml_, 9.67mmol) was added drop-wise to a suspension of methyl 4- amino-1 -methyl-1 H-pyrazole-3-carboxylate (p70, 1 g, 6.45 mmol), CuBr2 (1 .44 g, 6.45 mmol) and CuBr (924 mg, 6.45 mmol) in MeCN (25 ml_). The resulting mixture was stirred at 80 C for 2 hrs. After cooling to RT the volatiles were evaporated under vacuum and the residue was purified by FC on S1O2 column (eluting from cHex to 40% EtOAc) to afford methyl 4-bromo- 1 -methyl- 1 H-pyrazole-3-carboxylate (p71 , 500 mg, y= 35 %) as brown solid. MS (mlz): 220.9 [MH]+

According to the analysis of related databases, 637336-53-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; CREMONESI, Susanna; SEMERARO, Teresa; TARSI, Luca; GIBSON, Karl Richard; (116 pag.)WO2019/81939; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

42027-81-6, name is 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, 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. Formula: C5H7N3O3

Palladium 10% on carbon (0.2 g) was added to a solution of compound 20-c (1.1 g, 7 mmol) in ethanol (20 mL) under hydrogen gas atmosphere (1 atm). The mixture was reacted at 25 C. for 16 hours, filtered and the filtrate was concentrated under reduced pressure to give 20-b as a red oil (740 mg, yield 83%), which was directly used for the next step without purification. LC-MS (ESI): m/z=128[M+H]+.

The synthetic route of 42027-81-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GUANGZHOU MAXINOVEL PHARMACEUTICALS CO., LTD.; XU, Zusheng; ZHANG, Nong; WANG, Tinghan; SUN, Qingrui; WANG, Yuguang; (90 pag.)US2018/208604; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 660845-30-7, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C6H5ClF2N2O, 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. name: 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde

30 g of 1-methyl-3-difluoromethyl-5-chloro-4-carbaldehyde-1H-pyrazole obtained in step (2)Was added to a 250ml single-neck flask,100 ml of N, N-dimethylformamide,Adding 2 times the molar amount of anhydrous potassium fluoride,The reaction was complete by heating and refluxing for 5 hours.The solvent was distilled off under reduced pressure,The residue was added to 100 ml of water,Extracted with ethyl acetate,The ethyl acetate was dried over anhydrous magnesium sulfate,Ethyl acetate was distilled off to give 21 g of a brown solid.The brown solid is 1-methyl-3-(difluoromethyl)-5-fluoro-1H-pyrazole-4-carbaldehyde

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 660845-30-7, its application will become more common.

Reference:
Patent; Zhejiang Chemical Engineering Research Institute Co., Ltd.; Xu, Tianming; Hu, Weiqun; Kong, Xiaolin; Zhang, Ruirui; Zheng, Zhiwen; Zhu, Weigang; Chen, Jie; Huang, Hongying; Yuan, Jing; (49 pag.)CN106336380; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 100114-57-6, name is 3-Cyclopropyl-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 100114-57-6, SDS of cas: 100114-57-6

The procedure is similar to Step 1[N55y6629j in Example- 839. 0.5 g of 6-chloro-N-(4, 4-difluorocyclohexyl)-4-methylpyridin-2-amine gave 6-(3 -cyclopropyl- 1 H-pyrazol- 1 -yl)-N-(4, 4-difluorocyclohexyl)-4-methylpyridin-2-amine as a white solid (0.11 g, 19%). MS (M+1)+=333.1; 1H-NMR (400 MHz, DMSO-d6): 8.36 (s, 1H), 6.77 (s, 1H), 6.62 (d, J= 7.20 Hz, 1H), 6.18 (d, J= 5.20 Hz, 2H), 3.96 (s, 1H), 2.20 (s, 3H), 2.10-1.90 (m, 7H), 1.60-1.45 (m, 2H), 0.92-0.85 (m, 2H), 0.77-0.71 (m, 2H).

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

Reference:
Patent; CADENT THERAPEUTICS, INC.; ERIKSEN, Birgitte, Langer; GUSTAFSSON, Magnus; HOUGAARD, Charlotte; JACOBSEN, Thomas, Amos; JEFSON, Martin, R.; KLEIN, Jessica; LARSEN, Janus, Schreiber; LOWE, John, A., III; MCCALL, John, M.; STROØBAeK, Dorte; VON SCHOUBYE, Nadia, Lyb°l; KEANEY, Gregg, F.; (752 pag.)WO2017/210545; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 612511-81-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 612511-81-6 name is (1-Methyl-1H-pyrazol-3-yl)methanamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To methyl 4-chloro-3-methoxy-5-nitrobenzoate (1 g, 4.07 mmol) in DMSO (8 mL) were added (1 -methyl-1 H-pyrazol-3-yl)methanamine (0.498 g, 4.48 mmol) and K2C03 (0.731 g, 5.29 mmol), and the reaction mixture was stirred at 50 °C for 48 hours. The reaction was quenched with water (25 mL), and the resulting precipitate was collected by filtration and dried in vacuum over to afford crude methyl 3-methoxy-4-(((1 -methyl-1 H-pyrazol-3- yl)methyl)amino)-5-nitrobenzoate (740 mg) as an orange solid. LC-MS (ES) m/z = 321 [M+H]+. NMR (400 MHz, DMSO-c/6): delta 3.78 (s, 3H), 3.84 (s, 3H), 3.91 (s, 3H), 4.73 (s, 2H), 6.10 (d, J = 2.0 Hz, 1 H), 7.46 (d, J = 1 .8 Hz, 1 H), 7.61 (d, J = 2.0 Hz, 1 H), 8.19 (d, J = 2.0 Hz, 1 H), 8.36 (br. s., 1 H).

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; MEDINA, Jesus Raul; TIAN, Xinrong; NG DI MARCO, Christina; GRAYBILL, Todd L.; HEERDING, Dirk A.; LI, William Hoi Hong; MANGATT, Biju; MARTYR, Cuthbert D.; RIVERO, Raphael Anthony; (570 pag.)WO2019/49061; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic acid, 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 3112-31-0, Formula: C5H4N2O4

3,5-Pyrazoledicarboxylic acid monohydrate (8.02 g, 46.1 mmol) was dissolved in the mixture of dry DMF (35 ml), dry DCM (35 ml) and DIPEA (7.9 ml). l-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 3.37 g, 17.6 mmol), HOBt (2.28 g, 16.9 mmol), and DIPEA (3 ml, 2.23 g, 17.3 mmol) were added at RT. The solution was mixed for 10 min. Then, 2-[5-(3,4-dichlorophenyl)- furan-2-yl]ethylamine hydrochloride (3.46 g, 1 1.8 mmol) dissolved in the mixture of dry DCM (35 ml) and DIPEA (2.0 ml, 1.48 g, 11.5 mmol) was dropped to the solution at RT. After stirring overnight water was added. The product was extracted into ethyl acetate. The organic phase was washed with water, dried and evaporated. The crude product was purified by flash chromatography using DCM as an eluent. The product was triturated in hot methanol. NMR (400 MHz, DMSO- ): 2.95 (2H, t), 3.56 (2H, m), 6.33 (IH, d), 7.01 (IH, d), about 7.03 (IH, broad s), 7.61 (IH, distorted dd), 7.63 (IH, distorted d), 7.83 (IH, d), about 8.45 (IH, broad s), about 14.05 (IH, broad 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, 1H-Pyrazole-3,5-dicarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ORION CORPORATION; WOHLFAHRT, Gerd; TOeRMAeKANGAS, Olli; SALO, Harri; HOeGLUNG, Lisa; KARJALAINEN, Arja; KNUUTTILA, Pia; HOLM, Patrick; RASKU, Sirpa; VESALAINEN, Anniina; WO2011/51540; (2011); 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. 51516-70-2, name is 5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile

General procedure: Intermediate 4 (0.001mol) and 5 (0.001mol) were dissolved in pyridine, phosphorus oxychloride is slowly added dropwise under ice bath conditions, then at 40-60C reacted for 5-8h. Finally, the mixture was poured into 30mL saturated Na2CO3 solution and stirred well. After the mixture was acidified, the saturated CuSO4 solution was used to remove pyridine, which greatly improved the purity and yield of the product. The data for compounds 8I-8VI are provided in the supporting information.

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; Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 81 – 87;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 28466-26-4,Some common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, molecular formula is C3H5N3, 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.

A library of compounds in which R4 was various groups having the formula [CONHR »] was prepared by the process described above using 4-fluoro-3-nitrobenzoic acid, as follows: [72] Aldehyde resin was mixed with a primary amine (R17-NH2) in [DICHLOROETHANE] (DCE), triethylorthoformate (TEOF), and DMF (containing [1%] acetic acid) in a 1: 1: 1 ratio. After shaken overnight, sodium triacetoxyborohydride (20 eq. ) dissolved in DMF was added (Abdel-Magid, A. F. , et al., Tetrahedron Lett, 3 1: 5595-5598 (1990) ). After the mixture was shaken at room temperature overnight, the resin was filtered and washed with DMF (3 x 5 mL), [MEOH] [(3 X 5] mL), DMF [(3 X 5] mL), [MEOH] [(3 X 5] mL), and [CH2CL2] [(3 X 5] mL). The resin was washed twice with 5 mL DMF containing [1%] Hunig’s base. To the filtered resin was added a mixture of 4-fluoro-3-nitrobenzoic acid (FNBA, 10 eq. ) and diisopropylcarbodiimide (DIC, 5 eq. ) in 2: 1 DMF : DCM. After shaking at room temperature overnight, the resin was filtered and washed with DMF (3 x 5 mL) and [CH2C12] (3 x 5 mL). [73] The resin was shaken with a primary amine [(R2-NH2)] in DMF for 8 hrs, filtered, and washed with DMF (6 x 5 mL), [MEOH] [(3 X 5] mL), and CH2C12 (3 x 5 mL). The aryl nitro group was reduced by the addition of tin (II) chloride dihydrate (20 eq. , >2 M) and N-methyl morpholine (NMM, 20 eq. ) in N-methyl pyrrolidinone (NMP). After shaken at room temperature overnight, the resin was filtered and washed with NMP (3 x 5 mL), [MEOH] (3 x 5 mL), and [CH2CI2 (3 X 5] mL). The resulting resin was shaken at room temperature with cyanogen bromide (5 eq. ) overnight, filtered, and washed with CH2Cl2 (3 x 5 mL), [MEOH] (3 x 5 mL), and CH2CI2 (3 x 5 mL). To produce a free amine, the resin was shaken for 30 min. in CHCl2 with the addition of sodium methoxide in methanol, filtered, and washed with CH2Cl2 [(4 X 5] mL). [[74]] In the final diversification step, the resin was heated at 500 C in DMF with a mono- substituted epoxide [[RLCH (-CH2O-)].] After shaking for 2 to 4 days the resin was filtered and washed with DMF (5 x 5 mL), [MEOH] [(3 X 5] mL), and CH2Cl2 (3 x 5 mL). T he resin-bound benzimidazole was cleaved from the solid-support by treatment with TFA: [CH2C12] (2: 3) for 1 hour at room temperature.

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

Reference:
Patent; Taktix Corporation; WO2003/105779; (2003); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics