Tag: M.W=0-100

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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., Safety of 1H-Pyrazole-4-carbonitrile

To a suspension of 1H-pyrazole-4-carbonitrile (50.5 mg, 0.542 mmol), K3P04(233 mg, 1.084 mmol) and 6-(3-chloro-2-fluoro-6-iodophenyl)pyrimidin-4-ol (190 mg,0.542 mmol) in dioxane (0.24 mL) was added (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (38.6 mg, 0.271 mmol). The vial was then purged with Ar, Cul (5.16 mg, 0.027mmol) was added, and the vial was sealed. The reaction mixture was heated at 80 C.After 16 h, the reaction was cooled to rt, filtered, and the filtrate was concentrated. Purification by reverse phase chromatography gave 1 -(4-chloro-3 -fluoro-2-(6-hydroxypyrimidin-4-yl)phenyl)- 1 H-pyrazole-4-carbonitrile (74 mg, 43% yield) as an offwhite solid. MS(ESI)m/z: 316.3 (M+H). ?H NMR (400MHz, CD3OD) oe 8.54 (s, 1H),8.09 (d, J=0.9 Hz, 1H), 7.97 (s, 1H), 7.80 (dd, J=8.7, 7.8 Hz, 1H), 7.50 (dd, J=8.7, 1.7 Hz, 1H), 6.51 (t,J1.1 Hz, 1H).

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; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 31230-17-8, The chemical industry reduces the impact on the environment during synthesis 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, I believe this compound will play a more active role in future production and life.

Method 22; 2-Chloro-5-methyl-N-f5-methyl-lH-pyrazol-3-yl)pyrimidin-4-amine; To a solution of 2,4-dichloro-5-methylpyrimidine (1.25 g, 7.8 mmol) in EtOH (30 ml) was added 5 -methyl- leta-pyrazol-3-ylamine (756 mg, 7.8 mmol) and DIPEA (2.8 mL). The mixture was heated at 70 °C overnight. LC/MS showed the completion of the reaction. The title compound was obtained by filtration under vacuum as a white solid (700 mg). m/z 224.

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, 5-Methyl-1H-pyrazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/49041; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 288-13-1, These common heterocyclic compound, 288-13-1, name is 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.

4-Nitropyrazole is available commercially from the N.D. Zelinsky Institute, Organic Chemistry, Leninsky prospect 47, 117913 Moscow B-334, Russia. The compound may also be prepared as follows :- s Fuming nitric acid (9.5 ml) was added dropwise to a stirred solution of pyrazole(13.6 g) in glacial acetic acid (51 ml) that had been cooled to -100C using an ice-salt bath. A voluminous precipitate was formed. Acetic anhydride (27 ml) was added dropwise and the resultant mixture was stirred at ambient temperature for 2.5 hours. The mixture was poured onto ice and the acidity of the mixture was reduced to pH5 by the addition of potassium 0 carbonate. The precipitate was isolated by filtration. The resultant solid was dissolved in water and the aqueous solution was extracted with diethyl ether. The organic solution was dried over magnesium sulphate and filtered. Petroleum ether (b.p. 60-80°C, 50 ml) was added to the filtrate which was concentrated by evaporation to a volume of about 50 ml. A precipitate formed which was isolated by filtration. This solid was believed to be S 1-nitropyrazole (20.6 g); 1H NMR: (DMSOd6) 6.71 (s, IH), 7.88 (s, IH), 8.81 (s, IH). The compound may be explosive and should be handled cautiously.

The synthetic route of 288-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/99326; (2007); 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. 1453-58-3, name is 3-Methylpyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

3-Methyl-1H-pyrazole (0.66 g, 8 mmol) and potassium tertbutoxide (0.88 g, 7.8 mmol) were dissolved in dry dimethyl sulfoxide (DMSO) (5 mL) at room temperature. To the basic solution, 2-bromopyridine (1.17 g, 7.4 mmol) was added slowly under constant stirring, and the solution was heated to reflux under nitrogen for 12 h. Once the reaction completed, it was cooled to room temperature and extracted with water and ether. The organic layer was washed withwater and ether to remove DMSO and excess base. The organic layer was then isolated, dried over anhydrous Na2SO4, and filtered. The solvent was then removed under reduced pressure, and the resultant colorless oil was purified by column chromatography on silica gel (200e300 mesh) eluted with hexane/ethylacetate (9:1 v/v). 1H NMR (500 MHz, CD2Cl2) delta (ppm): 8.43 (1H, d, J 2.53), 8.38 (1H, d, J 4.88), 7.91 (1H, d, J 8.30), 7.79e7.74 (1H, m), 7.59-7.47 (1H, m), 6.25 (1H, d, J 2.53), 2.38 (3H, s).

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; Sunesh, Chozhidakath Damodharan; Subeesh, Madayanad Suresh; Shanmugasundaram, Kanagaraj; Chitumalla, Ramesh Kumar; Jang, Joonkyung; Choe, Youngson; Dyes and Pigments; vol. 128; (2016); p. 190 – 200;,
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. 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., SDS of cas: 31230-17-8

General procedure: A solution of 2,4-dichloroquinazoline (1.0 equiv.) in THF, triethylamine (1.2 equiv.) and alkylamine (1.2 equiv.) were added. The reaction stirred at room temperature until cannot see reactant spots on TLC. The solvent was removed by evaporated under reduced pressure, dissolved in ethyl acetate and washed with saturated sodium chloride and extracted. The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and dried under vacuum to give the compound as a solid

The synthetic route of 31230-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pobsuk, Nattakarn; Paracha, Tamkeen Urooj; Chaichamnong, Nattiya; Salaloy, Nattapas; Suphakun, Praphasri; Hannongbua, Supa; Choowongkomon, Kiattawee; Pekthong, Dumrongsak; Chootip, Krongkarn; Ingkaninan, Kornkanok; Gleeson, M. Paul; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 267 – 270;,
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. 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., name: 1-Methyl-1H-pyrazol-3-amine

Example 80; 4-Benzyloxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide; To a solution of 4-benzyloxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (77b) (6.98 g, 23.40 mmol) in CH2Cl2 (100 mL) was added thionyl chloride (2.04 mL, 28.1 mmol), followed by 10 drops of DMF. The mixture was refluxed for 2 h, then concentrated and dried under vacuum. The residue was dissolved in CH2Cl2 (100 mL), and 3-amino-1-methyl-pyrazole (2.73 g, 28.1 mmol) was added at 0° C., followed by triethylamine (6.52 ml, 46.80 mmol). The mixture was stirred at 0° C. to room temperature for 1 hr. The reaction was quenched with H2O, extracted with 3.x.CH2Cl2. The combined organic layers were dried over Na2SO4, concentrated and purified by flash column chromatography with 1-3percent MeOH in CHCl3 to give a white solid (5.31 g, 60percent yield). 1H NMR (400 MHz, CDCl3) delta 8.43 (s, 1H) 7.29-7.50 (m, 6H) 7.09 (d, J=1.01 Hz, 1H) 6.84 (dd, J=8.08, 1.77 Hz, 2H) 5.14 (s, 2H) 3.83 (s, 3H) 2.95-3.06 (m, 2H) 1.50 (s, 6H); LCMS for C22H23N3O3 m/z 378.20 (M+H+).

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; Pfizer Inc.; US2008/280875; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 31230-17-8, A common heterocyclic compound, 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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 solution of compound 12 (84 mg, 0.30 mmol) in DMF (3 mL) at room temperature were added DIPEA (0.103 mL, 0.6 mmol) and 5-methyl-1H-pyrazol-3-amine (88 mg, 0.9 mmol).The reaction mixture was heated at 40° C. overnight.Water was added, and the yellow precipitate was collected by filtration and washed with water.The solid was purified by silica gel chromatography eluting with DCM/MeOH to give compound I (30 mg, 29percent).1H NMR (300 MHz, DMSO-d6) delta 2.19 (s, 3H), 6.54 (s, 1H), 7.40 (m, 2H), 7.68 (t, 1H), 7.9-7.7 (m, 2H), 8.08 (m, 2H), 8.74 (d, 1H), 10.66 (s, 1H), 12.20 (s, 1H); LC-MS (ESI) m/z: 348 (M+H)+.

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; AMBIT BIOSCIENCES CORP.; US2012/53193; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1904-31-0, name is 1-Methyl-1H-pyrazol-3-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 1904-31-0, Formula: C4H7N3

(E)-(3-Chloro-4-methanesulfonyl-phenyl)-cyclopentyloxyimino-acetic acid (93 mg, 0.27 mmol), 1-methyl-1H-pyrazol-3-ylamine (29 muL, 0.30 mmol) and N,N-diisopropylethylamine (141 muL, 0.81 mmol) were combined in acetonitrile (1.25 mL) and cooled in an ice bath. O-(7-Azabenzotriazole-1-yl)-N,N,N’N’-tetramethyluronium hexafluorophosphate (103 mg, 0.27 mmol) was added and the ice bath was removed. After stirring 2 h, the reaction mixture was evaporated in vacuo. The residue was treated with saturated aqueous sodium bicarbonate solution (1 mL) and extracted with chloroform (2*3 mL). The combined organic phases were dried over sodium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (Merck silica gel 60, 40-63 mum; 60percent ethyl acetate/hexanes) to afford (E)-2-(3-chloro-4-methanesulfonyl-phenyl)-2-cyclopentyloxyimino-N-(1-methyl-1H-pyrazol-3-yl)-acetamide (79 mg, 69percent) as a white solid after lyophilization from aqueous acetonitrile: LC-MS (ESI) m/e calcd for C18H21ClN4O4S [M+] 424.10, found 425 [M+H+]; H1-NMR (400 MHz, CDCl3) delta ppm 1.64 (m, 4 H, 2*CH2), 1.86 (m, 4 H, 2*CH2), 3.29 (s, 3 H, SO2CH3), 3.85 (s, 3 H, NCH3), 4.88 (p, J=4.1 Hz, 1 H, OCH), 6.69 (d, J=2.3 Hz, 1 H, Ar), 7.28 (d, J=2.3 Hz, 1 H, Ar), 7.55 (dd, Jo=8.2, Jm=1.3 Hz, 1 H, Ar), 7.66 (d, Jm=1.3 Hz, 1 H, Ar), 8.18 (d, Jo=8.2 Hz, 1 H, Ar), 9.16 (s, 1 H, NH).

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-Methyl-1H-pyrazol-3-amine, other downstream synthetic routes, hurry up and to see.

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

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. 1453-58-3, name is 3-Methylpyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C4H6N2

Step C. [2-Methyl-5-(3-methyl-1H-pyrazol-1-yl)-phenyl]-(6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-6-yl)-methanone Sodium hydride (60percent suspension in oil, 0.25 g, 6.25 mmol) was washed with hexane, dried under nitrogen and resuspended in dry dimethylformamide (10 mL). Neat 3-methylpyrazole (0.28 mL, 3.5 mmol) was added in one portion at ambient temperature. Stirring was continued until the gas evolution subsided. The (5-fluoro-2-(methyl)-phenyl)-(6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-6-yl)-methanone of Step B (0.75 g, 1.94 mmol) was added in one portion to the clear solution. The mixture was heated to reflux for 26 hours, cooled and partitioned between water and ethyl acetate. The organic extracts were dried over sodium sulfate and evaporated to dryness. The residue was dissolved in dichloromethane and absorbed onto a silica Merck-60 flash column. Elution with hexane-ethyl acetate (gradient from 8:2 to 7:3) provided the title product (0.55 g) as a pale yellow foam which was crystallized by sonication from hexane-ethanol, m.p. 209-210° C.

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; American Home Products Corporation; US6235900; (2001); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 14884-01-6, 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 14884-01-6 as follows.

General procedure: A capped set of vials containing a mixture of the requisite pyrazole (0.051 mmol) and W2 (20.0 mg, 0.042 mmol) in dioxane (0.75 ml) was transferred into a glove box under an atmosphere of nitrogen. To each vial vial was added sodium tert-butoxide (12.2 mg, 0.127 mmol) followed by chloro[2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-l,r-biphenyl][2-(2- aminoethyl)phenyl)]palladium(II) (2.90 mg, 4.23 muiotaetaomicron). The vials were capped and placed into a preheated aluminum block at 100 C. The mixtures were stirred at that temperature for 24 hours. The vials were removed from the heating block, allowed to cool to RT and removed from the glove box. Water (1 mL) was added to each vial followed by DCM (2 mL). The mixtures were transferred to a Varian Bond Elute resovoir and the organic layer from each vial was drained into a new 2-dram vial. To each of the aqueous layers was added additional DCM (1 mL). The organic layer was again drained into the new set of 2-dram vials. The combined organic layers were dried in vacuo. Each crude residue was redissolved in 1 mL of DMSO and filtered. The crude products were purified by mass triggered preparative HPLC [Waters XBridge C18 column, 5muiotaeta, 19×100 mm, using a gradient range from 25-35% initial to 60- 70% final MeCN (0.1% NH4OH) in water (0.1% NH4OH), 25 mL/min, 12 min run time].

According to the analysis of related databases, 14884-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GILBERT, Eric, J.; CUMMING, Jared, N.; STAMFORD, Andrew, W.; YU, Younong; SCOTT, Jack, D.; ISERLOH, Ulrich; WANG, Lingyan; CALDWELL, John, P.; WO2014/62553; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics