Tag: M.W:100-200

Electric Literature of 5334-40-7,Some common heterocyclic compound, 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, molecular formula is C4H3N3O4, 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 1 1A.4-Nitro-1H-pyrazole-3-carboxylic acid methyl ester Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3-pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in MeOH (100 ml) at ambient temperature and the mixture stirred for 48 hours. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 14.4 (s, 1H), 8.9 (s, 1H), 3.9 (s, 3H)

The synthetic route of 5334-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/21420; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 5-Amino-1,3-dimethylpyrazole

The aldehyde derivative (0.1 mmol, 1.0 eq.) and the required amine (1.3 eq.) are dissolved in 95:5 MeOH/NMP (0.5 mL) in a glass vial, under inert atmosphere (N2) and treated with AcOH (2.0 eq.) and NaBH3CN (1.5 eq.). The reaction mixture is stirred at rt and monitored by LC-MS. Upon reaction completion, the reaction mixture is concentrated under reduced pressure. Purification of the residue gives the desired product. Starting from the compound of Preparation Q and 1,3 -dimethyl- lH-pyrazol-5 -amine and proceeding in analogy to Procedure Y, the title compound was obtained, after purification by prep-HPLC (basic conditions), as an amorphous solid (11% yield).MS (ESI, m/z): 339.09 [M+H+].

The synthetic route of 3524-32-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GUDE, Markus; HUBSCHWERLEN, Christian; PANCHAUD, Philippe; WO2011/121555; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 449758-17-2, name is 1-(2-Tetrahydropyranyl)-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 449758-17-2, name: 1-(2-Tetrahydropyranyl)-1H-pyrazole

To a solution of 1 -tetrahydropyran-2-ylpyrazole (762 mg, 5 mmol, 1 equiv.) intetrahydrofuran (35 ml) cooled at -78C is added n-butyllithium (2.5M in hexanes) (2.2ml, 5.5 mmol, 1.1 equiv.) dropwise. The mixture is warmed to 0C for 10 minutes and then is warmed to ambient temperature for 10 minutes. It is cooled to -78C and a solution of 2-oxo-3 -(2-trimethylsilylethoxymethyl)- 1,3 -benzothiazole-6-carbaldehyde (1.55 g, 5 mmol, 1 equiv.) in tetrahydrofuran (7 ml) is added. The mixture is stirred at -78C for one hour, quenched with aqueous saturated ammonium chloride, and extracted with ethyl acetate. The extracts are dried over sodium sulfate, filtered, and concentrated to an oil which is purified by silica chromatography eluting with 0-45% ethyl acetate in hexanes to afford 6- [hydroxy-(1 -tetrahydropyran-2-ylpyrazol-3 -yl)methyl] -3-(2- trimethylsilylethoxymethyl)-1,3-benzothiazol-2-one (1 .99g, 4.31 mmol, 86%) as amixture of diastereomers. LCMS (low pH): r.t. 2.27 mm.

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-(2-Tetrahydropyranyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; GARDINIER, Kevin Matthew; GERNERT, Douglas Linn; HAHN, Patric James; HOLLINSHEAD, Sean Patrick; KHILEVICH, Albert; MAYHUGH, Daniel Ray; ORNSTEIN, Paul Leslie; PORTER, Warren Jaye; REEL, Jon Kevin; SCHKERYANTZ, Jeffrey Michael; SPINAZZE, Patrick Gianpietro; STEVENS, Freddie Craig; WITKIN, Jeffrey Michael; (199 pag.)WO2015/183673; (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. 3469-69-0, name is 4-Iodopyrazole, A new synthetic method of this compound is introduced below., name: 4-Iodopyrazole

4-iodopyrazole (20 g) and ethanol (100 ml) were added and stirred uniformly. KOH (11.6 g) and KI (0.9 g) were added and the methyl chloride gas was introduced into the liquid surface, Control temperature 30_45 C, GC tracking reaction end, add water 100g, dichloromethane extraction (40gX3), Concentrated to no flow liquid, with n-heptane 6ml beating, suction filter white solid, dry, weighing 17.2g, GC purity 98%, yield 80%;

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; Dalian AllyChem Co.,Ltd(AllyChem); WANG, XIANXUE; ZHENG, PENG; (7 pag.)CN103601749; (2016); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 5334-39-4, 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 5334-39-4 as follows.

To a solution of 245 mg (1.19 mmol) of a mixture of 1 -(4-fluorobenzyl)-5-methyl-1 H- pyrazol-4-amine and 1 -(4-fluorobenzyl)-3-methyl-1 H-pyrazol-4-amine (intermediate 1C) in 4.0 mL DMSO was added 453 mg (1.19 mmol) HATU, 0.26 mL N,N- diisopropylethylamine and 200 mg (0.99 mmol) commercially available 2,6- dimethylquinoline-4-carboxylic acid. The reaction mixture was stirred for 20 hours at 25 C. This mixture was directly purified via preparative HPLC (method A1 ) to obtain 92 mg (23%) of the desired title compound together with 208 mg (51%) of the regioisomer N-[1 -(4-fluorobenzyl)-3-methyl-1 H-pyrazol-4-yl]-2,6-dimethylquinoline-4- carboxamide. 1 H NMR (500 MHz, DMSO d6): delta (ppm) = 2.22 (s, 3H), 2.48 (s, 3H), 2.68 (s, 3H), 5.31 (s, 2H), 7.16 – 7.26 (m, 4H), 7.53 (s, 1 H), 7.60 (dd, 1 H), 7.79 (s, 1 H), 7.85 (s, 1 H), 7.89 (d, 1 H), 10.12 (s, 1 H).

According to the analysis of related databases, 5334-39-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHMANN, Bernd; HEISLER, Iring; MUeLLER, Thomas; CLEVE, Arwed; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (194 pag.)WO2016/12474; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 175277-11-9, 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. 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows.

Using General Method A, 3-tert-butyl-1-methyl-1H-pyrazole-5-carboxylic acid (0.054 g, 0.3 mmol), Example A1 (0.1 g, 0.25 mmol), triethylamine (0.76 g, 0.75 mmol) and DPPA (0.137 g, 0.5 mmol) were combined and purified by column chromatography (ethylacetate/hexanes) to afford (4-(4-(4-(3-(3-tert-butyl-1-methyl-1H-pyrazol-5-yl)ureido)-3-fluorophenoxy)pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl pivalate as a white solid (0.115 g, 82% yield). 1H NMR (400 MHz, DMSO-d6): delta 8.89 (s, 1H), 8.84 (s, 1H), 8.68 (s, 1H), 8.50 (d, J=5.6 Hz, 1H), 8.19 (t, J=8.8 Hz, 1H), 7.46 (d, J=2.4 Hz, 1H), 7.33 (dd, J=12.0 Hz, 2.8 Hz, 1H), 7.06 (dd, J=8.8 Hz, 1.6 Hz, 1H), 6.97 (dd, J=5.6 Hz, 2.4 Hz, 1H), 6.35 (s, 2H), 6.07 (s, 1H), 3.60 (s, 3H), 1.19 (s, 9H), 1.10 (s, 9H); MS (ESI) m/z: 565.2 (M+H+).

The chemical industry reduces the impact on the environment during synthesis 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; US2008/261961; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

5334-43-0, name is 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile

General procedure: (General method). Amixture of the appropriate aminonitrile 1 (3.0 mmol) and1,3-dicarbonyl compound (3.0 mmol) in anhydrous toluene(12 ml) was refluxed for 1 h in a flask equipped with aDean-Stark trap. Tin(IV) chloride (3.0 g, 11.5 mmol) wasadded to the reaction mixture, and refluxing was continuedfor additional 5-6 h. A resinous precipitate was formed,andthe colorless toluene layer was decanted. The residualsolvent was removed on a rotary evaporator, the obtainedglassy solids were dissolved in boiling dioxane, cooled, thenpoured into a solution of Na23 (4.0 g) in water (70 ml).The precipitate that formed was filtered off, washed withwater, dried, and recrystallized from a 5:1 mixture of2-PrOH-DMF.

The synthetic route of 5334-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Potapov, Andrei Yu.; Vandyshev, Dmitriy Yu.; Kosheleva, Yevgeniya A.; Polikarchuk, Vladimir A.; Potapov, Mikhail A.; Shikhaliev, Khidmet S.; Chemistry of Heterocyclic Compounds; vol. 53; 2; (2017); p. 207 – 212; Khim. Geterotsikl. Soedin.; vol. 53; 2; (2017); p. 207 – 212,6;,
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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

General procedure: Under nitrogen atmosphere, carboxylic acid II (3mmol), EDCI (3.3 mmol), HOBT (3.3 mmol)and Et3N (1.8 mmol) were placed in a three-necked flask with 40 mL CH2Cl2, and stirred for 2 hat 0 C; then, compound I (2.4 mmol) was added to the flask and allowed to react for 3 h at 0 C.The reaction was monitored by thin-layer chromatography (TLC) (all reactions could be completed in3 h) and, on completion of the reaction, the mixture was washed with saturated NaHCO3 solutionand water, respectively. Then, it was dried over anhydrous Na2SO4, filtered and evaporated onrotavapor in vacuum. Subsequently, crude products III-1-III-18 were purified by silica gel columnchromatography [V (CH2Cl2): V (EA) = 3:1] and crude products III-19-III-36 were purified by silicagel column chromatography [V (PE): V (EA) = 3:1]. Finally, products were recrystallized with thedichloromethane/petroleum ether to obtain pure target compounds.

According to the analysis of related databases, 176969-34-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Shen; Meng, Siqi; Xie, Yong; Yang, Yonggui; Zhang, Yumeng; He, Lu; Wang, Kai; Qi, Zhiqiu; Ji, Mingshan; Qin, Peiwen; Li, Xinghai; Molecules; vol. 24; 14; (2019);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 2075-45-8, These common heterocyclic compound, 2075-45-8, name is 4-Bromo-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 mixture of 4-bromo- lH-pyrazole (500 mg, 3.40 mmol) in DCM (10 mL) was added Boc20 (0.790 mL, 3.40 mmol) and Et3N (0.948 mL, 6.80 mmol). The mixture was stirred at 25 C for 1 h. The mixture was concentrated to afford fert-butyl 4-bromo- lH-pyrazole-l-carboxylate (800 mg, 2.91 mmol, 86% yield). TLC (PE/EA = 2: 1, Rf = 0.6): lH NMR (400 MHz, CD3OD) delta 8.31 (s, 1H), 7.77 (s, 1H), 1.63 (s, 9H). ES-LCMS m/z 148.0 (M-Boc+H).

Statistics shows that 4-Bromo-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 2075-45-8.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; EIDAM, Hilary Schenck; DEMARTINO, Michael P.; GONG, Zhen; GUAN, Amy Huiping; RAHA, Kaushik; WU, Chengde; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; CHEUNG, Mui; WO2014/141187; (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 632365-54-9 as follows. Recommanded Product: 632365-54-9

To a refluxing mixture of 7.0 g (175 mmol) of sodium hydride (NaH 60% dispersion in mineral oil) and 10.45 g (88.5 mmol) [OF DIETHYL CARBO7LATE (CO (OETJ2)] in 100 mL of toluene was added dropwise via an addition funnel a mixture of 10 g [(44. 3] mmol) [OF 1- (4-BENZYLOXY-] [PHENYL)-ETHANO7LE] in 20 mL of toluene, and the resulting mixture was heated at reflux under argon for 1 h. The reaction mixture was then cooled to [0C,] quenched by the addition of 40 mL of acetic acid, during which time a yellow precipitate formed, and it dissolved upon subsequent addition of water. The separated organic layer was washed with saturated sodium bicarbonate solution, water and brine, dried over sodium sulfate and concentrated to give a residue which was chromatographed on silica gel (10% hexane in dichloromethane) to afford 9.2 g (70% yield) of desired [3-(4-BENZYLOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER] as indicated by 1H NMR. To a solution of 2 g (6.7 mmol) of 3-(4-benzyloxy-pyenyl)-3-oxo-propionic acid ethyl ester in 12 mL of ethanol (heated slightly for complete dissolution) was added dropwise 7 mL (7 mmol) [OF POTASSIUFN T-BUTOXIDE (KOTBU 1 MSOLUTION IN T-BUTANOL),] during which time a precipitate formed. The reaction mixture was stirred at rt for 20 min, then diethyl ether was added and the precipitate was collected by filtration, washed with ether and dried to afford 2.2 g (98% yield) of desired [3-(4-BENZYLOXY-PHE7LYL)-3-OXO-PROPIONIC ACID ETHYL ESTER POTASSIUM] salt as indicated by 1H NMR. A mixture 100 mg (0.3 mmol) of 3-(4-benzyloxy-phenyl)-3-oxo-propionic acid ethyl ester potassium salt, 86 mg (0.45 mmol) of 2-cyclohexylethyl bromide, and 17 mg (0.1 mmol) of potassium iodide (KI) in 1 mL [OF DIMETHYLFONNAMIDE (DMF)] in a 4 mL vial was shaken in a sand bath at [80 C] overnight. The mixture was then concentrated to give a residue which was purified via reverse-phase chromatography (Gilson) to afford (after lyophilization) 85 mg (70% yield) of 2- (4-benzyloxy-benzoyl)-4-cyclohexyl-butyric acid ethyl ester as a solid as indicated by LC-MS-calcd for [C26H3202 [M++H] +] : 409.23, found: 409.2. A mixture of 71 mg (0.171 mmol) [OF 2-(4-BENZYLOXY-BE7LZOYL)-4-CYCLOHEXYL-BUTYRIC ACID] ethyl ester, 24 mg (0.171 mmol) of [5-AMINO-1H-PYRAZOLE-3-CARBOXYLIC ACID METHYL ESTER,] 7 mg (20 [MOL%)] [OF P-TOLUEYLESULFOFZIC ACID MONOHYDRATE (PTSA),] and 3 mL of chlorobenzene was heated at [120 C] overnight. The reaction mixture was then concentrated to a residue which was purified via reverse-phase chromatography (Gilson) to afford (after lyophilization) desired 5-(4-benzyloxy-phenyl)-6-(2-cyclohexyl-ethyl)-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine- 2-carboxylic acid methyl ester as a solid as indicated by LC-MS-calcd for [C29H3LN304] [[M +H] +] : 486.23, found: 486.2. This material was then converted to 5-(4-benzyloxy-phenyl)- 6-(2-cyclohexyl-ethyl)-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (559) via the well known LiOH saponification protocol (10% yield over 2 steps); LC-MS-calcd for [C2SH29N304] [[M++H] +] : 472.22, found: 472.2. Note that the same synthetic sequence was carried out from the commercially available [3-FURAN-3-YL-3-OXO-PROPIONIC ACID ETHYL ESTER] as depicted above to give [6- (2-CYCLOHEXYL-ETHYL)-] 5-furan-3-yl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (612).

According to the analysis of related databases, 632365-54-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEOGENESIS PHARMACEUTICALS, INC.; WO2003/101993; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics