Day: May 27, 2021

Application of 31037-02-2, The chemical industry reduces the impact on the environment during synthesis 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

To a dry flask under nitrogen at 0C charged with 60 wt.% NaH (296 mg, 7.39 mmol) and ethyl 5-amino-l-methyl-lH-pyrazole-4-carboxylate (500 mg, 2.96 mmol) was added 10 mL THF. (0437) The mixture was stirred for 10 minutes at which point CS2 (1.782 mL, 29.6 mmol) was added by syringe. The mixture was allowed warm to room temperature then heated to 40C and stirred for 3H. After cooling the flask to 0C and iodine was added portion wise over 10 minutes. The mixture was stirred for another hour at 0C then 30 mL diethyl ether was added and the precipitate was filtered off. The filtrate was washed 3x with IN HC1, lx with brine and the organic portion was dried over sodium sulfate and the solvent removed yielding a reddish black solid. The crude product was purified by flash (0-30% EA in Hex) yielding the titled compound as a yellow solid (460mg, 2.178 mmol, 73.7 % yield). M+H found 212.0 XH NMR (400 MHz, CDCI3) delta 7.81 (s, 1H), 4.25 – 4.44 (m, 2H), 3.80 (s, 3H), 1.30 – 1.44 (m, 3H)

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, Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; LARSEN, Scott D.; HUDDLE, Brandt C.; YANG, Kun; BUCKANOVICH, Ronald; HURLEY, Thomas; (127 pag.)WO2017/223086; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

Reference Example 27: Ethyl-1-(5-fluoropyridin-2-yl)-1H-pyrazol-3-carboxylate To a solution of ethyl-1H-pyrazole-3-carboxylate (25.0 g, 178.4 mmol) and 2-bromo-5-fluoropyridine (47.1 g, 267.6 mmol) in DMF (300 mL), copper(I) iodide (8.5 g, 44.6 mmol), rac-trans-N,N’-dimethylcyclohexane-1,2-diamine (28.1 mL, 178.4 mmol) and Cs2CO3 (116.2 g, 356.8 mmol) were added, and the resulting mixture was stirred for 7 hours at 90°C. The reaction mixture was allowed to cool to room temperature, then water and EtOAc were added thereto, followed by filtration through Celite®. The organic layer was taken out from the filtrate, washed with a saturated aqueous solution of sodium chloride, dried over Na2SO4, then the drying agent was filtered off, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (HP-Sil 50 g, hexane/EtOAc = 70/30 to 0/100). The obtained solid was stirred and washed in hexane/EtOAc = 4/1 and filtered out to obtain the title compound (29.0 g) (colorless solid). MS (ESI pos.) m/z: 236 [M+H]+

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5932-27-4.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; FUTAMURA Aya; ARAKI Yuko; ABE Masahito; OHTA Hiroshi; SUZUKI Ryo; NOZAWA Dai; EP2862860; (2015); 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. 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

Reference of 31037-02-2,Some common heterocyclic compound, 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C7H11N3O2, 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 dry flask with gas inlet under nitrogen was charged with 25 mL THF and aniline (1.349 mL, 14.78 mmol). The flask was cooled to -78C and nBuLi in hexanes (2.1M, 5.67 mL, 14.19 mmol) was added slowly. After stirring for 30 min, solid ethyl 5-amino-l-methyl-lH-pyrazole- 4-carboxylate (2 g, 11.82 mmol) was added against a strong counterflow of nitrogen. The flask was allowed to warm to RT and stirred overnight. The next morning the flask was again cooled to -78C and another portion of nBuLi (2.1M, 5.67 mL, 14.19 mmol) was added and then the flask was warmed to RT. After 3 hours the reaction was quenched with sat. aq. ammonium chloride and the volatiles were removed. The residue was taken up in EtOAc and washed with water and brine before drying the organic portion over sodium sulfate and concentrating. The crude obtained was recrystallized from ethanol, yielding the titled compound as an orange crystalline solid (1.6 g, 7.40 mmol, 62.6 % yield). XH NMR (400 MHz, OMSO-d6) delta 9.38 (s, 1H), 7.89 (s, 1H), 7.68 (d, J= 7.83 Hz, 2H), 7.29 (t, J = 8.02 Hz, 2H), 6.93 – 7.11 (m, 1H), 6.31 (s, 2H), 3.54 (s, 3H)

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

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; LARSEN, Scott D.; HUDDLE, Brandt C.; YANG, Kun; BUCKANOVICH, Ronald; HURLEY, Thomas; (127 pag.)WO2017/223086; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 66121-71-9, name is 4-Cyano-1-methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Cyano-1-methylpyrazole

Step 3: 5-( 1-methyl-I H-pyrazol-4-yI)-2H-tetrazole1-mcthyl-IH-pyrazole-4-carbonitrile (18 gm, 0.168 moles) obtained instep 2, tn-nbutyl tin chloride (65 gm, 0.218 moles), sodium azide (14 gm, 0.20 Imoles) were taken in toluene (180 ml). The reaction mixture was stirred for 24 hours at 110-120C. The progress of the reaction was monitored by HPLC. The above reaction mixture was cooled to 10-15C, to this added 10% ethanolic HC1 solution (100 ml, pH= 1-2). The reaction mixture was stirred for 1-1.5 hours at 10i5C, filtered off the inorganic salts, washed with ethanol (30 ml). Themother liquor and washings were collected and toluene and ethanol were recovered at 50-55C at reduced pressure. To the abOve residue at 20-25C, added di-isopropyl ether (100ml), stirred for 1-2 hours at 20-25C, filtered the solid, washed with.di-isopropyl ether (30ml) and dried at 60-65C to yield the product, 5-(1-methyl-1H-pyrazol-4-yl)-2H-tetrazole.Drywt 25gmYield 1.4 w/w (99%)

According to the analysis of related databases, 66121-71-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RALLIS INDIA LIMITED; PALIMKAR, Sanjay Sambhajirao; PAWAR, Jivan Dhanraj; SANKAR, B; KADAM, Subhash Rajaram; HINDUPUR, Rama Mohan; PRABHU, Venkatesh M; PATI, Hari Narayan; SUPHALA, Vadiraj Gopinath; MANE, Avinash Sheshrao; WO2014/2110; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5334-39-4, name is 3-Methyl-4-nitro-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 5334-39-4, Quality Control of 3-Methyl-4-nitro-1H-pyrazole

A mixture of 3-methyl-4-nitro-lH-pyrazole ( 5 g, 39.34 rnmol), 2-bromoethanoi (9.83 g,78.68 mmol, 5.59 mL) and K2CO3 (16.31 g, 118.02 mmol) in CCN (50 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 80 C for 16 h under N2. The mixture was cooled to 20 C and concentrated under reduced pressure. The residue was poured into ice water (100 mL). The aqueous phase was extracted with EtOAc (3 chi 35 mL). The combined organic phase was washed with brine (35 mL), dried over anhydrous NaaSC^, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:EtOAc = 2: 1), to give 2-(5-methyl-4-nitro-pyrazol- 1 -yl)ethanol and 2-(3-methyl-4-nitro-pyrazol-1-yl)ethanol as a yellow oil. LCMS: RT 0.161 min, m/z = 172.2 [M+H]~. -1 NMR (400 MHz, CDC13): delta 8.20 (s, 1 H), 8.03 (s, 1 H), 4.14 – 4.22 (rn, 4 H), 3.94 – 4.03 (m, 4 H), 3.07 (d, 1=5.27 Hz, 2 H), 2.64 (s, 3 H), 2.47 (s, 3 H).To a solution of 2-(5-methyl-4-nitro-pyrazol-l-yl)ethanol (19-2, 4.26 g, 24.89 mmol,), 2-(3-methyl-4-nitro-pyrazol-l-yl)ethanol and Cul (948 mg, 4.98 mmol,) in CH3CN (100 mL) was added a solution of 2,2-difluoro-2-fiuorosulfonyl-acetic acid (6.65 g, 37.34 mmol, 3.87 mL) in CH3CN (10 mL) dropwise at 55 C over a period of 30 min under N2. The reaction mixture was stirred at 55 C for another 2 h. The mixture was cooled to 20 C and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:EtOAc = 5: 1 ), to give a mixture of l-[2- (difluoromethoxy)ethyl] -5 -methyl -4-nitro-pyrazole and 1 – [2-(difiuoromethoxy)ethyl -3 -methyl -4-nitro- pyrazole as a yellow oil. LCMS: RT 0.707 min, m/z = 222.1 [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, 3-Methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); 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. 3994-50-1, name is 1-Methyl-4-nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 3994-50-1

Example 25Synthesis of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(1-methyl-1H-pyrazol-4-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amineThe compound was synthesized according to Method A.A mixture of 0.996 g (8.82 mmol) of 4-nitropyrazole (J. Med. Chem. 2005, 48, 5780-5793) and 1.33 g (10.6 mmol) of dimethyl sulphate in 10 mL of 1 M NaOH was heated at 35 C. for 48 hrs. The reaction mixture was cooled to RT and the precipitate was filtered, washed with water, and dried to give 0.561 g (50% yield) of 1-methyl-4-nitro-1H-pyrazole: 1H NMR (DMSO-d6) delta8.83 (s, 1H), 8.22 (s, 1H), 3.91 (s, 3H).A mixture of 0.144 g (1.14 mmol) 1-methyl-4-nitro-1H-pyrazole, 0.017 g (0.07 mmol) platinum oxide, and ethyl acetate (5 mL) in ethanol (15 mL) was stirred under 2 atmospheres of hydrogen for 14 hrs. The catalyst was removed by filtration through a pad of celite and the solvent was removed to give 0.080 mg (73% yield) of 4-amino-1-methyl-1H-pyrazole as a purple residue, which was used in the next step without further purification: 1H NMR (DMSO-d6) delta6.98 (s, 1H), 6.88 (s, 1H), 3.76 (br s, 2H), 3.65 (s, 3H).A mixture of 0.405 g (4.27 mmol) of 4-amino-1-methylpyrazole and 0.695 g (1.90 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-1H-benzimidazole in DMSO (5 mL) was heated at 125 C. for 15 min. The reaction mixture was cooled to room temperature and water was added. The solid was collected by filtration, washed with water, and dried. Chromatography on alumina, eluting with hexanes/EtOAc (1:1) gave a brown powder. Recrystallization from ethanol/CH2Cl2 gave 0.145 g (18% yield) of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(1-methyl-1H-pyrazol-4-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine: mp 225-226 C.; 1H NMR (DMSO-d6) (rotamers) delta10.00 (s, 1H), 9.73 (s, 0.2H), 8.60 (d, J=8.0 Hz, 1H), 8.29 (d, J=7.6 Hz, 0.2H), 7.92 (t, JHF=52.8 Hz, 1H), 7.86-7.80 (m, 2.6H), 7.68 (t, JHF=52.6 Hz, 0.2H), 7.59 (s, 1H), 7.52-7.42 (m, 2.9H), 3.85-3.82 (m, 8.4H), 3.75-3.73 (m, 4.8H); Anal. Calcd. for C19H19F2N9O 0.06EtOAc 0.24H2O: C, 52.9; H, 4.6; N, 28.8. Found: C, 52.9; H, 4.5; N, 28.6%.

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; Pathway Therapeutics Limited; US2011/9405; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 175137-46-9, name is 5-Cyclopropyl-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 175137-46-9, category: pyrazoles-derivatives

To a solution of 2,4-difluoro-l -nitrobenzene (1.76 g, 11.1 mmol) and DIEA (1.93 ml, 11.1 mmol) in TEtaF (20 ml) was added dropwise a solution of 5-cyclopropyl-lH-pyrazol-3- amine (0.91 g, 7.39 mmol) in TEtaF (5 ml) at 25 C. After addition, the reaction mixture was stirred at 80 0C for 48 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : DCM : EtOAc = 2 : 1 : 1) to give the title compound as a yellow solid (0.62 g, 32%). NMR (400 MHz) 12.37 (s, IH), 9.83 (s, IH), 8.25 (m, IH), 7.98 (d, J= 11.2 Hz, IH), 6.75 (m, IH), 5.95 (s, IH), 1.90 (m, IH), 0.96 (m, 2H), 0.72 (m, 2H).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/87530; (2006); 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. 3469-69-0, name is 4-Iodopyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C3H3IN2

(1) Add 19.4 g (0.1 mol) of 4-iodopyrazole, 10.1 g (0.12 mol) of 3,4-dihydro-2H-pyran, and 0.7 g (0.006 mol) of trifluoroacetic acid into the reaction bottle and stir to heat Micro-reflux for 12 hours, the reaction formula of step (1) is as follows:After cooling to room temperature, 0.24 g (0.006 mol) of sodium hydride was added to neutralize the reaction system, and distillation under reduced pressure gave 27.8 g of 4-iodo-1- (tetrahydro-2H-pyran-2-yl) -1H-pyrazole, The product is directly put into the next reaction without purification

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

Reference:
Patent; Changsha Luxing Biological Technology Co., Ltd.; Tan Yongjun; Yang Bing; Zhu Zhiping; Zhang Jianhua; (10 pag.)CN110734401; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 345637-71-0, A common heterocyclic compound, 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, molecular formula is C7H7F3N2O2, 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.

a) Preparation of 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester To a solution of (5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid (9.1 g, 36.1 mmol) in DMF (100 mL) is added diisopropylethylamine (45 mL, 216 mmol), followed by O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate (15.5 g, 39.7 mmol). After stirring 15 min at RT, 2-piperidin-4-yl-thiazole-4-carboxylic acid ethyl ester hydrochloride (10 g, 36.1 mmol) is added to the reaction mixture. After stirring overnight at RT, solvent is evaporated and the resulting yellow oil is dissolved in ethylacetate (300 mL), washed with saturated aqueous sodium bicarbonate solution (300 mL), 1M HCl solution (300 mL), and brine (100 mL). The organic layer is dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude mixture is purified by column chromatography on silica gel (dichloromethane/methanol 10:1) to give 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)acetyl]piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester. 1H-NMR (400 MHz, CDCl3): delta=1.40 (t, 3H), 1.70-1.85 (m, 2H), 2.16-2.30 (m, 2H), 2.32 (s, 3H), 2.79-2.89 (m, 1H), 3.22-3.43 (m, 1H), 4.03-4.12 (m, 1H), 4.42 (q, 3H), 4.54-4.69 (m, 1H), 4.93-5.08 (2d, 2H (diastereotopic)), 6.35 (s, 1H), 8.10 (br, 1H). MS: m/z=209 (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; SYNGENTA PARTICIPATIONS AG; Umarye, Jayant; Berthon, Guillaume; Cederbaum, Fredrik Emil Malcolm; Luksch, Torsten; Lamberth, Clemens; Sulzer-Mosse, Sarah; Kanjilal, Pranab; Sonawane, Ravindra; US2014/243371; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics