Tag: M.W:100-200

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

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: 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

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

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

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

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

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. 3469-69-0, name is 4-Iodopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: pyrazoles-derivatives

4-Iodo-lH-pyrazole (20.0 g, 103 mmol) is dissolved in anhydrous THF (150 ml) and trimethylsilyl acetylene (72.8 ml, 515 mmol) is added under an inert atmosphere. Diethyl- amine (150 ml), bis-(triphenylphosphine) palladium (II) chloride (10.8 g, 15 mmol) and copper iodide (2.9 g, 15 mmol) are added and the reaction mixture is left to stir at room temperature for 3 hours. The solvent is removed under reduced pressure. The residue is dissolved in diethyl ether and the insoluble impurities are filtered off. The solvent is removed under reduced pressure. The residue is dissolved in methanol and the insoluble impurities removed. The solvent is removed under reduced pressure. The residue is purified by dry flash chromatography on silica gel eluting with a gradient system of diethyl ether : /so-hexane (20:80 to 100:0) to afford the title compound [MH+] 165.07 1H NMR (DMSO) : 0.00(s, 9H), 7.45 (s, IH), 7.90 (s, IH), 12.90 (br s, IH)

The synthetic route of 3469-69-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/74925; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 3994-50-1, name is 1-Methyl-4-nitro-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. Safety of 1-Methyl-4-nitro-1H-pyrazole

Example 1 5-chloro-1-methyl-4-nitro-1H-pyrazole To a 500 mL round bottom flask containing 4-nitro-1-H-pyrazole (5 g, 44.2 mmol) was added sodium hydroxide (1M, 200 mL) and dimethyl sulfate (31 mL, 330 mmol). The mixture was stirred at room temperature for 72 h and the mixture was extracted with CH2Cl2 (2*150 mL). The organic layer was separated and the solvent was distilled off to yield 1-methyl-4-nitro-1H-pyrazole as a white solid (4.30 g, 76%). Following WO 2007/99326, to a 500 mL 3-neck-round bottom flask was added 1-methyl-4-nitro-1H-pyrazole (4.30 g, 33.8 mmol) and THF (12 mL). The mixture was cooled to -78 C. and lithium hexamethyldisilazide in THF (1M, 88.4 mL, 90 mmol) was added dropwise via an addition funnel over 20 min. The brown mixture was stirred for 30 min and warmed to -45 C over 30 min. The mixture was cooled back down to -78 C. and hexachloroethane (10.5 g, 44.2 mmol) dissolved in THF (20 mL) was added via an addition funnel over 15 min. The mixture was stirred for 2.5 h, warmed from -78 C to -40 C and the reaction was monitored by LCMS. Upon completion of the reaction, the reaction was quenched with a solution of saturated NH4Cl (150 mL), and ethyl acetate (100 mL) was added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layer was washed with water (150 mL), dried over Na2SO4 and the organic solvent was distilled off. The crude product was purified via flash chromatography (CH2Cl2/7% MeOH) to yield 5-chloro-1-methyl-4-nitro-1H-pyrazole as a white solid (1.40 g, 20%). 1H NMR (400 MHz, CDCl3) delta 8.13 (s, 1H), 3.92 (s, 3H); ESIMS m/z=162.0 (M+1)

The synthetic route of 1-Methyl-4-nitro-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wang, Xiaojing; US2011/251176; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1384973-12-9,Some common heterocyclic compound, 1384973-12-9, name is 5-Amino-3-bromo-1H-pyrazole-4-carbonitrile, molecular formula is C4H3BrN4, 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.

5-amino-3-bromo-1H-pyrazole-4-carbonitrile (3.74 g, 0.02 mol) was added to the reaction flask.Potassium carbonate (5.53 g, 0.04 mol) and DMF (35 mL),Heat to 60 C and stir for half an hour.Add bromoisopropane (2.95 g, 0.024 mmol),Stir at this temperature for 6 hours.Cool, filter, and concentrate to dryness.Extracted with dichloromethane (200 mL),Washed twice with saturated saline solution,Dry over anhydrous sodium sulfate and concentrate the organic phase.The silica gel sample is quickly passed through the column.Obtained white solid 5-amino-3-bromo-1-isopropyl-1H-pyrazole-4-carbonitrile (3a) 2.56 g,Yield: 55.9%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-3-bromo-1H-pyrazole-4-carbonitrile, its application will become more common.

Reference:
Patent; Huang Chuanman; (18 pag.)CN108530436; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics