Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 1190380-49-4, name is 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine, 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 1190380-49-4, category: pyrazoles-derivatives

Into a 100-mL round-bottom flask was placed compound 14.2 (85 mg, 0.24 mmol, 1.00 eq.), n-BuOH (15 mL), 1-(oxan-4-yl)-1H-pyrazol-4-amine (61 mg, 0.36 mmol, 1.50 eq.), and hydrogen chloride in dioxane (1 mL, 4N). The resulting solution was stirred for 30 h at 110 C in an oil bath and then concentrated in vacuo. The resulting solution was diluted with H20. The pH value of the solution was adjusted to 10 with sodium carbonate and the solids were collected by filtration. The solid was dried under infrared light. This resulted in 71.4 mg (61%) of I-22 as an off-white solid. LC-MS (ESI, m/z): [M+H+]= 481.2; 1H NMR: (4d-MeOD, ppm): 7.881 (1H, s), 7.594 (1H, s), 7.055-7.065QH, m), 6.053-6.063 (1H, m), 4.310-4.411(1H, m), 4.048-4.310 (3H, m), 3.974 (3H, s), 3.623-3.743 (4H, m), 3.537-3.623 (2H, m), 2.634-2.644 (4H, m), 2.275-2.409 (3H, m), 2.019-2.167 (6H, m), 1.335-1.563 (4H, m).

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, 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; BOYCE, Sarah; (135 pag.)WO2017/4133; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 17827-61-1, name is Methyl 1-Methylpyrazole-3-carboxylate, 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. COA of Formula: C6H8N2O2

Step B: 1 -Methyl- lH-pyrazole-3-carboxamide (3)A solution of methyl l-methyl-lH-pyrazole-3-carboxylate (1.1 g, 7.9 mmol) in NuEta32Omicron (10 mL) was stirred for 2 h at room temperature. The solvent was evaporated to give the crude product which was used for the next step without further purification.

The synthetic route of Methyl 1-Methylpyrazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; MCCOMAS, Casey, C.; REGER, Thoma, S.; QI, Changhe; WO2014/150114; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 20154-03-4,Some common heterocyclic compound, 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, molecular formula is C4H3F3N2, 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-trifluoromethylpyrazole (5.0 g, 36 mmol), triethylamine (7.0 mL, 50 mmol) in dichloromethane (40 mL) was added dimethylsulfamoyl chloride (5.5 mL, 51 mmol), and the reaction mixture was heated at reflux for 2 days. The resulting mixture was cooled to ambient temperature and filtered through a pad of silica gel using dichloromethane as eluent. The filtrate was then concentrated under reduced pressure to give an amber residue. The resulting residue was dissolved in diethyl ether. The ether solution was washed with water, dried (MgSC^), and concentrated under reduced pressure to give 8.71 g of the title compound. 1HNMR (CDCl3) delta 3.01 (s, 6H), 6.65 (s, IH)5 8.03 (s, IH).

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

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2008/13622; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 4058-91-7,Some common heterocyclic compound, 4058-91-7, name is 5-Amino-1-methyl-1H-pyrazole-4-carboxylic acid, molecular formula is C5H7N3O2, 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 stirred solution of Step 3 intermediate (800 mg, 5.666 mmol) in dry DMF (8 ml), 2-bromo- l-(2-chlorophenyl)ethanone (1.32 g, 5.666 mmol) was added followed by potassium fluoride (500 mg, 8.499 mmol) at room temperature and the resultant reaction mixture was stirred overnight. The mixture was quenched with water (75 mL) and ethyl acetate (30 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with water (2 x 100 mL) and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue obtained was purified by flash silica gel column chromatography to afford 912 mg of the desired product as a solid. lH NMR (300 MHz, DMSO-d6): delta 3.54 (s, 3H), 5.31 (s, 2H), 6.31 (s, 2H), 7.43-7.53 (m, 1H), 7.55 (d, = 4.8 Hz, 1H), 7.77 (d, = 7.5 Hz, 2H), 7.95 (s, 1H).

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-1-methyl-1H-pyrazole-4-carboxylic acid, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; KUMAR, Sukeerthi; CHAUDHARI, Sachin Sundarlal; GHARAT, Laxmikant Atmaram; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; MUKHOPADHYAY, Indranil; (327 pag.)WO2018/203298; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 7119-95-1,Some common heterocyclic compound, 7119-95-1, name is 1-Nitropyrazole, molecular formula is C3H3N3O2, 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 15 (E)-4-{3-[2-(3-Chloro-4-methanesulfonyl-phenyl)-2-cyclopentyloxyimino-acetylamino]-pyrazol-1-ylmethyl}-benzoic acid methyl ester A solution of 1-nitro-1H-pyrazole (4.00 g, 35.4 mmol) in 40 mL of benzonitrile was refluxed for 2 h. After being cooled to 25° C., the mixture was poured into hexanes (160 mL). A white solid precipitated which was filtered and dried in vacuo, to afford 3-Nitro-1H-pyrazole (3.16 g, 79percent): H1-NMR (400 MHz, DMSO-d6) delta7.01 (1H, d, J=2.4 Hz), 8.01 (d, 1H, J=3.4 Hz).

The synthetic route of 7119-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Berthel, Steven Joseph; Kester, Robert Francis; Murphy, Douglas Eric; Prins, Thomas Jay; Ruebsam, Frank; Tran, Chinh Viet; Vourloumis, Dionisios; US2008/146625; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 37718-11-9, These common heterocyclic compound, 37718-11-9, name is 1H-Pyrazole-4-carboxylic 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.

To a mixture of lH-pyrazole-4-carboxylic acid (5.00 g, 44.6 mmol) in dry CH3OH (100 mL) was added drop-wise H2S04 (874 mg, 8.92 mmol) at 0C. The mixture was stirred at reflux overnight. A solution of NaOH (3.83 g, 95.7 mmol, 10 N) was added drop- wise to the reaction mixture. The mixture was poured into ice-water and diluted with ethyl acetate. The organic layer was washed with saturated aqueous lithium chloride solution and brine successively, dried over anhydrous Na2SC>4 and concentrated. The residue was purified by silica gel chromatography (petroleum ether : ethyl acetate = 10 : 1) to give methyl 1H- pyrazole-4-carboxylate (4.50 g) as a white solid. LC-MS (ESI) found: 127 [M+H]+.

The synthetic route of 37718-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZAFGEN, INC.; ZAHLER, Robert; VATH, James E.; (130 pag.)WO2018/31877; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic 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 175277-11-9, name: 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid

27) 3-(tert-butyl)-N-(3-methoxy-4-methylbenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of 3-Methoxy-3-methyl-benzaldehyde (250 mg, 1.66 mmol, 1.0 eq) in toluene (20 mL) was added 2,4-dimethoxybenzyl amine (306 mg, 1.83 mmol, 1.1 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (20 mL) and then NaBH4 (129 mg, 3.32 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in Ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (1.66 mmol, 1.0 eq) in DMF (20 mL) were added the acid (333 mg, 1.83 mmol, 1.1 eq), DIEA (1.07 g, 8.32 mmol, 5 eq) and HBTU (757 g, 1.99 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (75 mL) and washed with 10% aqHCl (1*50 mL), sat NaHCO3 (1*50 mL) and water (4*50 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25% to 75%)) to give the amide, which was directly used in the next step. The amide was treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product in (263 mg, >95% purity). Mass Spectrum (LCMS, ESI Pos.) Calcd. For C18H26N3O2: 316.0 (M+H), Found 316.0.

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, 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Prosetta Antiviral ,Inc.; Selvarajah, Suganya; Paulvannan, Kumar; (58 pag.)US2018/118679; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 52867-42-2, name is Methyl 2-methyl-5-oxo-2,5-dihydro-1H-pyrazole-3-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 52867-42-2, Product Details of 52867-42-2

Methyl-3-(difluoromethoxy)-1-methyl-1H-pyrazole-5-carboxylate A solution of 2.00 g (12.8 mmol) of methyl 3-hydroxy-1-methyl-1H-pyrazole-5-carboxylate (preparation: Chem. Ber. 1974, 107, 1318-1328) in 28 ml of N,N-dimethylformamide is admixed with 5.09 g (32.0 mmol, 96%) of chlorodifluoroacetic acid sodium salt and 2.66 g (19.2 mmol) of potassium carbonate, and the reaction mixture is heated at 80 C. overnight. The reaction mixture is added to 300 ml of water and extracted several times with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and concentrated by evaporation in vacuo on a rotary evaporator. Chromatographic purification gives 1.07 g of methyl-3-(difluoromethoxy)-1-methyl-1H-pyrazole-5-carboxylate (40%). 1H-NMR (400 MHz, d6-DMSO): delta=7.19 (t, 1H), 6.55 (s, 1H), 4.00 (s, 3H), 3.55 (s, 3H) ppm. HPLC-MS: log P=2.04; mass (m/z)=207 [M+H]+.

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, Methyl 2-methyl-5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer CropScience AG; US2011/301181; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 75415-03-1, 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. 75415-03-1, name is 2-(1H-Pyrazol-3-yl)pyridine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 16 Synthesis of 2-(1-(2-fluoro-4-nitrophenyl)-3-pyrazolyl)pyridine (18a) Compound 17a (1 g, 6.9 mmol) obtained from the aforesaid process and 3,4-difluoronitrobenzene (0.74 mL) were dissolved in N,N-dimethylformamide (20 mL), and then anhydrous potassium carbonate (1.9 g) was added thereto. The mixture was reacted at 100 C for 4 hours. After completion of the reaction, the reactant mixture was cooled to room temperature. Water was added to the mixture, resulting in a substantial amount of precipitate. Then, the precipitate wassuction-filtered, and the filter cake was recrystallized with acetone to get the product 18a as a white powder (1.7 g), witha yield of 93.4%.[0110] 1H-NMR (400 MHz, CDCl3 ): delta 8.69-8.70 (m, 1H), 8.39-8.44 (m, 1H), 8.26-8.27 (m, 1H), 8.15-8.21 (m, 2H),8.11-8.13 (m, 1H), 7.78-7.82 (m, 1H), 7.30-7.32 (m, 1H), 7.22 (d, J= 2.4 Hz, 1H)

The synthetic route of 2-(1H-Pyrazol-3-yl)pyridine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SICHUAN GOODDOCTOR PHARMACEUTICAL GROUP CO., LTD.; Si Chuan University; LUO, Youfu; WANG, Zhenling; WEI, Yuquan; GENG, Funeng; EP2738169; (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. 138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 4-nitro-1H-pyrazole-3-carboxylate

Compound 6 and 6A: To a mixture containing 5 (3.1 g, 18.1 mmol) and potassium carbonate (5.0 g, 36.2 mmol) in 60 mL of acetone was added methyl iodide (2.2 mL, 36.2 mmol). The resulting solution was heated and stirred at 70 C. for 2 hours. After the reaction mixture was cooled to room temperature, water was added and the mixture was extracted with ethyl acetate (×3). The combined organics were washed with brine, dried (MgSO4), and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel using 20% ethyl acetate in hexanes as the eluent to afford 6 (1.1 g, 33%) as white solid. 1H NMR (d6-DMSO) delta 3.96 (s, 3H) 3.98 (s, 3H) 8.36 (s, 1H); ES (+) MS m/e=186 (M+1) and using 30% ethyl acetate in hexanes to afford 6A (2.2 g, 66%) as white solid. 1H NMR (d-CDCl3) delta 3.98 (s, 3H) 4.00 (s, 3H) 8.13 (s, 1H); ES (+) MS m/e=186 (M+1).

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:
Patent; Sunesis Pharmaceuticals, Inc.; US2007/27166; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics