Tag: M.W=0-100

Synthetic Route of 1453-58-3, A common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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 suspension of hexane washed potassium hydride (0.424 g) in dimethylformamide (5 ml) was treated in one portion with 3-methyl pyrazole (0.85 ml) while stirring. After the gas evolution ceased, 2-chloro-4-fluorobenzoic acid methyl ester (2.0 g, 10.6) was added to the clear solution and heated at 130° C. for 15 minutes. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and brine. The organic phase was washed with water, brine,. and dried over anhydrous sodium sulfate. Removal of solvent in vacuo afforded 2.2 g of a yellow oil. (Note: 20percent hydrolysis of the ester was detected by analysis of the NMR spectrum of the crude product). The desired regioisomer 2-chloro-4-(3-methyl-1H-pyrazol-1-yl)-benzoic acid methyl ester was isolated from the other isomer (described below) by flash column chromatography on silica gel (Merck 60) eluting with dichloromethane-hexane 2:1) to give 1.55 g of the title compound as a colorless solid. MS (EI m/z: 250/252 (M)+. [00283] The 5-regioisomer, namely 2-chloro-4-(5-methyl-1H-pyrazol-1-yl)-benzoic acid methyl ester was isolated from the above flash column chromatography on silica gel (Merck 60) by further eluting with dichloromethane-hexane 2:1 to give 0.20 g of the product as a colorless solid. MS (EI), m/z: 250/252 (M)+.

The synthetic route of 1453-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6831079; (2004); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 694-48-4, The chemical industry reduces the impact on the environment during synthesis 694-48-4, name is 1,3-Dimethyl-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Put 100g (1.04mol, 1eq) of 1,3-dimethylpyrazole into the reaction bottleWith 400 mL of ethanol, 166.4 g (1.04 mol, 1.00 eq) of bromine was added dropwise with stirring at 5-10C.React at 5-10 for 4 hours,Sampling GC to check the remaining material is less than 1%, add 300mL water,Then add 200mL of saturated aqueous sodium thiosulfate solution to quench,Distilling ethanol under reduced pressure, cooling to 0 ,Filtered180.2g of 4-bromo-1,3-dimethyl-1H-pyrazole,GC purity 94.3%,The yield is 99%

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, 1,3-Dimethyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xuzhou Shengyuan Chemical Co., Ltd.; Chen Hong; Yu Wanli; (8 pag.)CN111233768; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 28466-26-4, A common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, molecular formula is C3H5N3, 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.

Neat 1 H-pyrazol-4-amine (49.0 mg, 0.59 mmol) was added in one charge to a stirred solution of 2-[(phenylmethyl)oxy]-5-(4-pyndinyl)benzoic acid (may be prepared as described in Description 79; 150 mg, 0.49 mmol), EDC (283 mg, 1.47 mmol) and HOBT (226 mg, 1.47 mmol) in dimethylformamide (4 ml) in air at room temperature. The reaction mixture was stirred at room temperature overnight. 30 ml water was added, and the mixture was extracted with ethyl acetate (70 ml x 2). The organic layers were combined, dried over MgS04l and concentrated in vacuo. The residue was further purified by pre-HPLC (Gilson GX-281 ; Shimadzu 15mueta? 250*20mm; A: l OmMolNH4HC03/Water; B: CH3CN) to yield the title compound as a white solid. 50 mg.1HNMR (400 MHz, DMSO-cfe): 5.34 (s, 2H), 7.34-7.44 (m, 4H), 7.55 (d, 2H), 7.74 (d, 4H), 7.95-7.98 (m, 1 H), 8.09 (d, 1 H), 8.62 (d, 2H), 10.25 (s, 1 H), 12.65 (s, 1 H).MS (electrospray): m/z [M+H]+ = 371

The synthetic route of 28466-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1904-31-0,Some common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.

97 Preparation of N.N-dicyclopropyl-6-ethyl- 1 -methyl -4-( 1 -methyl- 1H- pyrazol-3-ylamino)-1.6-dihydroimidazo[4.5-dlpyrrolo[2.3-blpyridine-7-carboxamide[00465] To a vial containing 1 -methyl- lH-pyrazol-3 -amine (11.89 mg, 0.122 mmol), Pd2(dba)3 (4.67 mg, 5.10 muiotaetaomicron), Xantphos (5.90 mg, 10.20 muiotaetaomicron), and cesium carbonate (100 mg, 0.306 mmol) was added 4-bromo-N,N-dicyclopropyl-6-ethyl-l- methyl-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 97A, 41.0 mg, 0.102 mmol) in DME (1020 muKappa). The reaction mixture was sparged with argon for 5 min, the vial was capped, and the reaction mixture was heated at 60 °C for 4 h and 80 °C for 16h. The reaction mixture was concentrated in vacuo. The crude residue was purified by flash column chromatography using an Isco 40 g column eluting with 0 – 5percent MeOH/ (3/4(3/4 followed by additional purification with preparative HPLC. N,N-Dicyclopropyl-6-ethyl-l-methyl-4-(l -methyl- lH-pyrazol-3 – ylamino)-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (13 mg, 0.030 mmol, 29.5percent yield) was isolated as a white solid.[00466] MS (ESI) m/z 419.3 (M+H) [00467] 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.17 (s, 1 H), 7.64 (s, 1 H), 7.31 (d, 1H, J= 2.26 Hz), 7.16 (d, 1 H, J= 2.26 Hz), 6.86 (s, 1 H), 4.65 (q, 2 H, J = 7.03 Hz), 4.01 (s, 3 H), 3.85 (s, 3H), 2.78 – 2.87 (m, 2 H), 1.49 (t, 3 H, J= 7.15 Hz), 0.81 – 0.89 (m, 4 H), 0.71 – 0.80 (m, 4 H)

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok V.; GREBINSKI, James W.; HART, Amy; INGHRIM, Jennifer; SCHROEDER, Gretchen; WAN, Honghe; WO2011/28864; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 288-13-1, name is 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 288-13-1, Quality Control of 1H-Pyrazole

General procedure: A mixture of the appropriate N-nucleophile (2 mmol), 4-bromonitrobenzene(2 mmol), t-ButOK or KOH (in the case of 1g, 1h)(2.2 mmol) in dimethyl sulfoxide (2.5 mL) was stirred at 60 C for 5 h(8 h in the case of 1b). After cooling and addition of water (60 mL),either a solid precipitated which was filtered, washed with water andrecrystallised from an appropriate solvent to give the product, or asuspension was generated which was extracted with ethyl acetate(3 × 30 mL), dried over Na2SO4, concentrated under reduced pressureand recrystallised from an appropriate solvent to give the desiredproduct

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:
Article; Ghasemi, Zarrin; Shahrak, Nasim Shahi; Roomi, Behzad Jalali; Zakeri, Ziba; Journal of Chemical Research; vol. 39; 2; (2015); p. 73 – 75;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 930-36-9,Some common heterocyclic compound, 930-36-9, name is 1-Methylpyrazole, molecular formula is C4H6N2, 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.

Methylpyrazole (4.1 g, 50 mmol, 1 equiv) and anhydrous DMF (11.6 ml, 3 equiv) were placed in a 100 ml of two-neck flask which was equipped with a Allihn condenser (a CaC12 drying tube was connected thereto) and a constant- pressure dropping thnnel, and the flask was placed in the oil bath of 90 C. Phosphorus oxychloride (5.6 ml, 1.2 equiv) was added dropwise over a period of 1 h. After the addition was completed, the mixture was stirred for a further 2 h. Then the solution was cooled and poured into a lot of ice water. The resulting mixture was brought to pH 4-5 with a solution of 10% NaOH solution and then extracted with dichloromethane several times until the product in the aqueous phase is little. The combined organic phase was washed with a small amount of brine twice, dried over MgSO4, filtered and then evaporated in vacuo to give the crude product of 1-me- thyl-1H-pyrazole-4-carbaldehyde, which can be directly used in the next step without further separation.

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

Reference:
Patent; Shen, Jianhua; Wang, Yiping; Wang, Kai; US2014/171431; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 132712-71-1 as follows. Quality Control of 3-Methyl-1H-pyrazol-5-ol

General procedure: Dichloromethane (10 mL) was taken in a round-bottomed flask,into which 1.0 equivalent (1 mmol) of triethylamine and pyrazolonewere poured. The mixture was stirred for 2 min without heating. To this mixture, 1.0 equivalent of corresponding presynthesized benzylidene from malononitrile was added. Then the mixture was agitated for 25-30 min. The reaction was observed by TLC. The desired products appeared as precipitates. The precipitates were washed with water to remove the unreacted pyrazolone to obtain pure products. Melting points were recordedfor crystalline substances.

According to the analysis of related databases, 132712-71-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kashtoh, Hamdy; Muhammad, Munira Taj; Khan, Jalaluddin J.A.; Rasheed, Saima; Khan, Ajmal; Perveen, Shahnaz; Javaid, Kulsoom; Atia-Tul-Wahab; Khan, Khalid Mohammed; Choudhary, M. Iqbal; Bioorganic Chemistry; vol. 65; (2016); p. 61 – 72;,
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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1192-21-8

A magnetically stirred solution of amine 5 (10.0 g, 103 mmol) inTHF (250 mL) was treated with potassium tert-butoxide (23.0 g,205 mmol) at 0 C. The resultant suspension was brought to roomtemperature and stirred for 1 h before the dropwise addition of ofluoronitrobenzene(12 mL, 113 mmol). The reaction mixture wasstirred for 3 h, quenched with water (300 mL) and extracted withEtOAc (3 150 mL). The combined organic extracts were dried(MgSO4), filtered and concentrated under reduced pressure. Thecrude oil was purified by flash column chromatography (silica, 3:5v/v EtOAc:hexanes) and concentration of the relevant fractions(Rf 0.42 in 1:1 v/v EtOAc:hexanes) afforded the title compound(16.9 g, 77percent) as yellow crystals.1H NMR (300 MHz, Chloroform-d): d 9.11 (s, 1H, NH), 8.25 (d,J 8.1 Hz, 1H), 7.56e7.54 (m, 1H), 7.52e7.38 (m, 1H), 6.96e6.84 (m,1H), 6.78e6.74 (m, 1H), 6.20 (d, J 2.5 Hz, 1H), 3.76 (s, 3H). 13C NMR(75 MHz, Chloroform-d): d 142.7, 139.0, 136.8, 136.3, 133.4, 126.6,118.7, 115.8, 101.8, 35.2. IR (diamond cell, neat) nmax: 3297, 3094,1609, 1572, 1509, 1490, 1340, 1221, 1145, 1075, 1043, 927, 750 cm1.LRMS (ESI) m/z: 219 ([MH], 100percent). HRMS (ESI) Found:(MNa), 241.0697. C10H10N4O2 requires (MNa), 241.0696. MP:133e135 C.

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 1192-21-8.

Reference:
Article; Jorgensen, William T.; Gulliver, Damien W.; Katte, Timothy A.; Werry, Eryn L.; Reekie, Tristan A.; Connor, Mark; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1644 – 1656;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1192-21-8, 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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

7-(2-Chloro-5 -methylpyrimidin-4-yl)-2-(2-methoxyethyl)-3 ,3 -dimethyl-3 ,4- dihydropyrrolo [1 ,2-a]pyrazin- 1 (2H)-one (48 mg, 0.14 mmol), i-methyl-i H-pyrazol-5 – amine (14.70 mg, 0.15 mmol) and cesium carbonate (90 mg, 0.28 mmol) were suspendedin tert-butanol (4 mL) and de-gassed for 10 minutes, then BrettPhos 3rd generation precatalyst (6.24 mg, 6.88 jimol) was added. The reaction was heated to 80 °C for 2 hours under nitrogen. The mixture was cooled to room temperature, diluted with EtOAc (50 mL), washed with saturated aqueous sodium bicarbonate (10 mL) and the layers separated. The aqueous portion was washed with ethyl acetate (50 mL) and the combined organics weredried (Na2SO4) and concentrated in vacuo to a yellow gum. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, Sji silica, 30 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1percent NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 2-(2-methoxyethyl)-3 ,3 -dimethyl-7-(5 -methyl-2-(( 1-methyl-i H-pyrazol-5 – yl)amino)pyrimidin-4-yl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (2H)-one (44.0 mg, 78 percent) as an off white solid. ?H NMR (500 MHz, DMSO, 30 °C) 1.11 (6H, s), 2.11 – 2.14 (3H, m),3.08 (3H, s), 3.25 (2H, t), 3.38 (2H, t), 3.49 (3H, s), 3.93 (2H, s), 6.06 (1H, d), 7.01 (1H, d), 7.13 (1H, d), 7.38 (1H, d), 8.04 (1H, d), 8.87 (1H, s). m/z: ES+ [M+H]+ 410.

The synthetic route of 1-Methyl-1H-pyrazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 694-48-4,Some common heterocyclic compound, 694-48-4, name is 1,3-Dimethyl-1H-pyrazole, molecular formula is C5H8N2, 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.

In a three-necked reaction flask equipped with a stirrer, 50 ml of acetic anhydride and 12.7 g of nitric acid were added,1,3-dimethylpyrazole 9.7 g of acetic anhydride in 10 ml was slowly added dropwise to the mixed acid,Add 50-60 degrees after the end of the reaction until the reaction is complete,Cooled to room temperature to add 100 grams of ice water,Filtered and dried to give 12 g of 4-nitro-1,3-dimethylpyrazole,LC purity 80%, yield: 84%.

The synthetic route of 694-48-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Hande Chuanghong Biochemical Technology Co., Ltd.; Mao Zhongping; Ma Dongxu; Ge Yonghui; Ren Xuejing; Tan Jin; (9 pag.)CN106674116; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics