Tag: M.W=0-100

Synthetic Route of 35344-95-7, A common heterocyclic compound, 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, molecular formula is C4H4N2O, 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 li/-pyrazole-4-carbaldehyde (300 mg, 3.12 mmol) was added ethyl 2-(triphenylphosphoranylidene)acetate (1360 mg, 3.90 mmol) in toluene (10 mL). The mixture was heated at 90 °C for 2 h. The solvent was removed in vacuo. The crude material was purified by flash chromatography to afford Example 7A (450 mg, 2.71 mmol, 87percent yield) as a white solid. LCMS (ES): m/z 167.1 [M+H]+.

The synthetic route of 35344-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; DEVASTHALE, Pratik; YE, Xiang-Yang; SELVAKUMAR, Kumaravel; DHANUSU, Suresh; BALASUBRAMANIAN, Palanikumar; GUERNON, Leatte R.; CIVIELLO, Rita; HAN, Xiaojun; PARKER, Michael F.; JACUTIN-PORTE, Swanee E.; (290 pag.)WO2018/89353; (2018); 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. 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Methyl-1H-pyrazol-3-amine

Compound la (3.64 g. 20 mmol), 3-amino-5-me- thyl-pyrazole (1.94 g, 20 mmol) and diisopropylethylamine (5.17 g, 40 mmol) were added to 20 mE of ethanol solution and then stirred at room temperature for 2 days. The insoluble substance was collected to obtain Compound lb (3.7 g, Yield76percent), MS [M+l] 244.0.

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 31230-17-8.

Reference:
Patent; ZHEJIANG HISUN PHARMACEUTICAL CO., LTD.; Ding, Yili; Yang, Xuan; Yan, Qingyan; Bai, Hua; Cai, Lifeng; Smith, Kenneth; Chai, Jian; US2014/378488; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1120-82-7,Some common heterocyclic compound, 1120-82-7, name is (1H-Pyrazol-1-yl)methanol, molecular formula is C4H6N2O, 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.

The three compounds were prepared by the same procedure analogue for L1. L1 was prepared by a similar procedure asdescribed in the literature [21]. The CH2Cl2 solution (10.0 mL) ofpyrimidinamine (1.15 g, 12.09 mmol) was added to the CH2Cl2 solution(10.0 mL) of 1H-1-pyrazolyl-1-methanol (1.86 g,12.09 mmol). The reaction solution was dried over MgSO4 afterstirring at room temperature for 4 days. The filtrate solvent, underreduced pressure, produced a transparent oil andwas recrystallizedusing a mixture of methanol with a few drops of ether. The whitecrystals obtained after 3 days were filtered and washed withmethanol (2 50 mL), followed by washing with Et2O (2 50 mL)to yield the final product (L1). 2.2.1.1. The N-((1H-pyrazol-1-yl) methyl) pyrimidin-2-amine (L1).White cristal. Yield (1.8 g, 85.3%). mp 418 K. FT-IR, cm1: 1077(CeN), 3080 (CeH, HeC]CeH), 1333 (C]N), 1380 (N]N), 1582(C]C), 3234 (NeH). UVevis (l 298 nm). 1H NMR(300 MHz,DMSO): dH 5.37 (d, 2H, CH2), 6.27 (t, 1H, CHPyr), 6.54 (t,1H, CHAr), 6.71 (t, 1H, NH), 7.47 (d, 1H, CHPy), 7.78 (d, 1H, CHPyr), 8.20(d, 1H, CHAr), 8.21 (d, 1H, CHAr). 13C NMR (75 MHz, CDCl3):dC 73.70 (CH2), 106.15 (CHPy), 110.55 (CHAr), 112.30 (CHPy), 129.85(CHPy), 139.74 (CHAr), 158.45 (CHAr), 164.02 (C).

The synthetic route of 1120-82-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Titi, Abderrahim; Messali, Mouslim; Alqurashy, Bakhet A.; Touzani, Rachid; Shiga, Takuya; Oshio, Hiroki; Fettouhi, Mohammed; Rajabi, Mehdi; Almalki, Faisal A.; Ben Hadda, Taibi; Journal of Molecular Structure; vol. 1205; (2020);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 14884-01-6, These common heterocyclic compound, 14884-01-6, name is 4-Methoxy-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.

To a solution of ethyl 1 -(6-(2-(4-(3-bromopropoxy)-2-methylphenethyl)-5-fluorophenyl)pyridin-2-yl)-5-(trifl uoromethyl)- 1 H-pyrazole-4-carboxylate (see Intermediate12 for prep) (200 mg, 0.315 mmol) in N,N-dimethylformamide (3 mL) was added cesiumcarbonate (154 mg, 0.473 mmol) and 4-methoxy-1H-pyrazole (46.4 mg, 0.473 mmol) and the reaction mixture was heated at 70 00 for 16 hours. The reaction mixture was cooled to room temperature, filtered through celite pad and the solid was washed with EtOAc (3X25 mL). The filtrate was concentrated under reduced pressure. The crude was purified by column chromatography eluting with 25-26% of EtOAc-hexane to afford ethyl 1-(6-(5-fluoro-2-(4-(3-(4-methoxy- 1 H-pyrazol- 1 -yl)propoxy)-2-methylphenethyl)phenyl)pyridin-2- yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate (60 mg, 0.069 mmol, 21.79% yield) as a gum. LC/MS: rt=4.29min, mlz=652.32 [M+H]

The synthetic route of 14884-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GOODMAN, Krista B.; KRAUSS, Achim Hans-Peter; LE MONNIER DE GOUVILLE, Anne-Charlotte; DODIC, Nerina; WO2015/33307; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1120-82-7, name is (1H-Pyrazol-1-yl)methanol, 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 1120-82-7, Safety of (1H-Pyrazol-1-yl)methanol

General procedure: A solution of primary diamine (one equiv.) in acetonitrile(20 mL), was slowly added to a solution of 2a or 2b (fourequiv.) in 60 mL of acetonitrile. The reaction mixture was stirred under refluxed for 6h then dried over MgSO4. The solvent was removed under reduced pressure. The solid was dried using a Schlenk line.

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-Pyrazol-1-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Abrigach, Farid; Bouchal, Btissam; Riant, Olivier; Mace, Yohan; Takfaoui, Abdelilah; Radi, Smaail; Oussaid, Abdelouahad; Bellaoui, Mohammed; Touzani, Rachid; Medicinal Chemistry; vol. 12; 1; (2016); p. 83 – 89;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 132712-71-1, 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. 132712-71-1, name is 3-Methyl-1H-pyrazol-5-ol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

SBA-Pr-NH2 (0.02 g) was activated into a round-bottomed flask containing a magnetic stirrer at 100 C for removal of the adsorbed water. The mixture of ninhydrin (1 mmol, 0.178 g), 1,2-aryl-diamines (1 mmol), and SBA-Pr-NH2 in 5 ml ethanol was heated and stirred at 60 C to form indenoquinoxaline A; then, after about 5 min, malono derivatives (1 mmol) and alpha-methylencarbonyl compounds (1 mmol)were added to the mixture of reaction for the synthesis of spiro[indeno[2,1-b]quinoxaline derivatives under reflux condition using MW irradiation (400 W, 80 C). Completion of the reaction was monitored by TLC. After that, obtainedprecipitate was cooled to room temperature and extractedfrom the solvent. Subsequently, the precipitate was dissolvedin minimum volume of hot acetone and the unsolvable SBA-Pr-NH2 catalyst was removed by filtration. The residue was purified by recrystallization from ethanol. The new compound was characterized by mass, IR, and NMR spectroscopy techniques. The melting points of the products were compared with those reported in the literature.

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

Reference:
Article; Ahmadi, Tahereh; Mohammadi Ziarani, Ghodsi; Bahar, Shahriyar; Badiei, Alireza; Journal of the Iranian Chemical Society; vol. 15; 5; (2018); p. 1153 – 1161;,
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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C4H3N3

To a solution of compound F5 (150 mg, 0.329 mmol) in acetone (5 mL) was added K2C03 (68.1 mg, 0.493 mmol) and 1 H-pyrazole-4-carbonitrile (45.8 mg, 0.493 mmol). After stirring at 25 C for 3 h, LCMS showed the reaction was complete. The reaction mixture was filtered, and the filtrate was concentrated in vacuum to give the crude product (150 mg). The crude product was purified by prep. HPLC (HC1) to give the desired product 170 (13 mg, 8.41%) as white solid. 1H NMR (170) (yield 8.4%): (400 MHz, CDC13) delta 7.86(s,lH), 7.81 (s, 1H), 5.03-4.87 (m, 2H), 3.54(d, J= 9.2Hz, 1H), 3.68-3.41 (m, 2H), 3.24 (d, J= 9.2Hz,lH), 2.59 (t, J= 9.2Hz, lH), 2.21- 1.15 (m, 29H), 0.65 (s, 3H). LCMS tR = 0.949 min in 1.5 min chromatography, 5-95AB, purity 98.6%, MS ESI calcd. for C28H42 3O3 [M+H]+ 467, found 450[M+H-18]+.

The synthetic route of 31108-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGE THERAPEUTICS, INC.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, Gerald; HERR, Robert, Jason; KARGBO, Robert, Borbo; WO2015/27227; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 35344-95-7, 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. 35344-95-7 name is 1H-Pyrazole-4-carbaldehyde, 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 the stirred solution of lH-pyrazole~4~carbaldehyde 46-3 (461.54 mg, 4.80 mmol) and (l-benzy~4~ piperidyl) methanesulfonate 46-2 (1.2 g, 4.46 mmol) in DMF (20 mL) was added cesium carbonate (3.35 g, 10.28 mmol). Reaction mixture was heated at 80C for 16 hours and was then cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. Crude material was purified by combiflash chromatography eluting at 0 1% methanol in dichlorometha e to afford l~(l-benzyl~4- piperidyl)pyrazole-4-carbaldehyde 46-4 (650 mg, 2.41 mmol, 70.42% yield) as brown gum. LC MS: ES+ 269 8.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Pyrazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; C4 THERAPEUTICS, INC.; VEITS, Gesine, Kerstin; HE, Minsheng; HENDERSON, James, A.; NASVESCHUK, Christopher, G.; PHILLIPS, Andrew, J.; GOOD, Andrew, Charles; (471 pag.)WO2019/191112; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 3920-50-1,Some common heterocyclic compound, 3920-50-1, name is Pyrazole-3-carboxaldehyde, molecular formula is C4H4N2O, 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 1H-pyrazole-3-carbaldehyde (5.00 g, 52.0 mmol, CAS: 3920-50-1) and BnBr (9.34 g, 54.6 mmol) in DMF (50 mL) was added Cs2CO3 (42.4 g, 130 mmol). The reaction mixture was stirred at 25 C. for 1 hour. On completion, the reaction mixture was diluted with water, extracted with ethyl acetate (3×100 mL). The combined organic layers was washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (Petroleum ether: Ethyl acetate=20:1) to give the title compound (8.00 g, 83% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 10.02 (s, 1H), 7.44 (d, J=2.4 Hz, 1H), 7.43-7.33 (m, 3H), 7.29-7.24 (m, 2H), 6.85 (d, J=2.4 Hz, 1H), 5.42 (s, 2H).

The synthetic route of 3920-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 37599-58-9, These common heterocyclic compound, 37599-58-9, name is (1H-Pyrazol-3-yl)methanamine, 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 5 mL microwave reaction vial equipped with a stirbar was charged with 4-fluoro-2- hydroxy-5-(N-(4-isopropoxyphenyl)sulfamoyl)benzamide (Example 107, 0.250 gl) and (1 H-pyrazol-3-yl)methanamine (0.198 g). The solids were taken up in 1 -butanol (3.4 mL) and the resulting reaction mixture was subjected to microwave irradiation at 1 10 C with stirring on high absorption setting for 2 sessions of 2 h each for a total of 4 h reaction time. The reaction mixture was resubjected to microwave irradiation at 140 C with stirring for an additional 2 sessions of 2 h and 8 h (14 h total microwave reaction time). The mixture was then cooled to room temperature, diluted with ethanol to ~20 mL total volume, filtered, and concentrated to a residue. The residue was taken up in a minimum amount of DMSO for purification by reverse phase silica gel using a 30 gram RediSep Gold C18 reverse phase silica cartridge (0-90% acetonitrile in 0.2M aq ammonium acetate). Fractions containing the desired material were pooled and then concentrated to remove the acetonitrile. The aqueous layer was acidified to ~pH 4.5 by addition of 1 N aq hydrochloric acid. The mixture was extracted twice with ethyl acetate and the organic layers were pooled, dried over sodium sulfate, filtered, and concentrated to dryness. The solid mass was triturated with diethyl ether to afford the title compound as an off-white solid (52 mg. LCMS m/z 446.3 (M+H)+. 1H NMR (400 MHz, DMSO-c/6) delta ppm 1 .13 – 1 .23 (m, 6 H) 4.38 (d, J=5.58 Hz, 2 H) 4.47 (spt, J=6.04 Hz, 1 H) 6.13 (s, 1 H) 6.16 (d, J=2.03 Hz, 1 H) 6.63 – 6.81 (m, 3 H) 6.89 – 7.01 (m, 2 H) 7.62 (br. s., 2 H) 8.06 (s, 1 H) 8.27 (br. s., 1 H) 9.81 (br. s., 1 H) 12.52 (br. s., 1 H) 13.74 (br. s., 1 H).

The synthetic route of 37599-58-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics