Tag: M.W:100-200

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. 13745-17-0, name is 4-Bromo-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C4H3BrN2O2

Ste 2: (0585) Preparation of 4-bromo-N-(2,2-dimethoxyethyl)-1H-pyrazole-3-carboxamide: (0586) [00242] To a stirred solution of 4-bromo-1H-pyrazole-3-carboxylic acid (3.4 g, 17.8 mmol) in dichloromethane (100 mL) were added triethylamine (12.42 mL, 89.00 mmol) and 2,2-dimethoxyethanamine (2.9 mL, 26.70 mmol) at room temperature. The reaction mixture was cooled to 0 C and 1-propanephosphonic anhydride solution (T3P) (15.89 mL, 26.70 mmol, 50% in ethyl acetate) was added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water (200 mL) and extract with dichloromethane (3 x 100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound 4-bromo-N-(2,2-dimethoxyethyl)-1H-pyrazole-3- carboxamide (3.6 g, crude) as a white solid. Calculated (M-H): 276.01; Found (M-H): 276.0.

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; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

1384973-12-9, name is 5-Amino-3-bromo-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. Formula: C4H3BrN4

General procedure: A mixture of halide (1 .0 eq.), boronic acid or pinacol ester (1 .5 eq.) and potassium carbonate (2.0 eq.) in 1,4-dioxane and water (3:1, 0.1 M)was degassed by bubbling nitrogen through it for 15 mi 1,1- bis(diphenylphosphino)ferrocene-palladium(ll) dichloride dichloromethane complex (0.05 eq.) was added and the mixture was degassed again by bubbling nitrogen through it for 15 mm. The mixture was then heated under microwave irradiation at 120-140 C for 60-90 mm. The reaction mixture was either purified by SCX SPE cartridge and used as such or purified using the following procedure, unless stated used crude. The mixture was filtered through a pad of Celite. The cake was rinsed with DCM. Water was added to the filtrate and the layers were partitioned. The aqueous layer was extracted with DCM (x2). The combined organic extracts were filtered over phase separator and then concentrated under reduced pressure to give a dark solid. Further purification by flash column chromatography gave the desired compound.; General procedure D, 5-fluoro-N-[[2-fluoro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenyl]methyl]-2-methoxy-benzamide (1 .65 mmol) and 5-amino-3-bromo-1 H-pyrazole-4-carbonitrile (1.34 mmol) gave, after purification, titled compound (0.78 mmol). UPLC-MS (ES, Short acidic): 1.67 mi m/z 384.0 [M+H]

The synthetic route of 1384973-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (266 pag.)WO2017/103611; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 660845-30-7, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, 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 660845-30-7, Product Details of 660845-30-7

In a 500 ml flask, 6.0 g (31 mmol) of 5-chloro-3-(difluoromethyl)-1 -methyl-1 H-pyrazole-4-carbaldehyde are added to 30 ml of toluene. A solution of 2.4 g (62 mmol) of sodium hydroxide in 6 ml of water is added to the reaction mixture, followed by 103 ml of a 30% solution of hydrogen peroxide in water, whilst keeping the temperature below 37 C. After the end of the addition, the reaction mixture is stirred at 50 C for 7 hours. Once the reaction mixture is back to room temperature, the two phases are separated and the organic phase is extracted with 100 ml of water. The combined aqueous phases are acidified to pH 2 with aqueous hydrochloric acid. The resulting white precipitate is filtered, washed twice with 20 ml of water, and dried to yield 3.2 g of 5-chloro-3-(difluoromethyl)-1 -methyl-1 H-pyrazole-4-carboxylic acid as a white solid. H NMR (400 MHz, DMSO-c/6) delta ppm : 3.78 (s, 3H); 7.12 (t, 1 H, JHF = 53.60 Hz)13.19 (s, 1 H); IR (KBr) : 1688 cm”1 (C=0); 2200-3200 cm”1 broad (hydrogen bond).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; BENTING, Juergen; DAHMEN, Peter; DESBORDES, Philippe; GARY, Stephanie; HADANO, Hiroyuki; VORS, Jean-Pierre; WACHENDORFF-NEUMANN, Ulrike; WO2012/52491; (2012); A2;,
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. 143426-52-2, name is 1-(4-(Chloromethyl)phenyl)-1H-pyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C10H9ClN2

N-(trans-2-hydroxycyclohexyl)-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide (224 mg), 1-[4-(chloromethyl)phenyl]-1H-pyrazole (125 mg), tripotassium phosphate trihydrate (330 mg) and Pd(dppf)Cl2 DCM (25.0 mg) were stirred in a mixed solution of 1,4-dioxane (10 mL) and water (1 mL) under a nitrogen atmosphere at 80C for 16 hr. To the reaction mixture was added ethyl acetate, and the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (49.0 mg).

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; Takeda Pharmaceutical Company Limited; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 57999-06-1, 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. 57999-06-1, name is 4-Phenyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of aminoazole 1f-i (1 mmol), acetoacetamides 2a-c (1 mmol), and aromatic aldehyde 3b-f (1 mmol) in 10 mL of ethanol was ultrasonicated at room temperature for 90 min in a round-bottom flask equipped with condenser. The reaction mixture was allowed to stand up to 12 h at room temperature and then was filtered to give the solid compounds 8a-i, which were washed with ethanol and air dried. Reaction products were obtained in high purity and did not require further purification by recrystallization.

The synthetic route of 4-Phenyl-1H-pyrazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Muravyova, Elena A.; Desenko, Sergey M.; Rudenko, Roman V.; Shishkina, Svetlana V.; Shishkin, Oleg V.; Sen’ko, Yulia V.; Vashchenko, Elena V.; Chebanov, Valentin A.; Tetrahedron; vol. 67; 48; (2011); p. 9389 – 9400;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 139756-02-8, A common heterocyclic compound, 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, molecular formula is C8H14N4O, 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.

Synthesis of Bb; Step 7: 4-amino-i -methyl-3 -propyl- 1 H-pyrazole-5-carboxamide (1 eq) and 3 -Nitrobenzaldehyde (1.1 eq ) were suspended in methanol 5 ml and the mixtureheated at 65 C for 1.5 hours after conformation of forming of imine by TLC. Added CuC12 (3 eq) and the reaction mixture heated at7O C under 02 for 2.5 hours. After completion of the reaction, the methanol was removed under vacuum. Then workup with ethyl acetate and water. Separate the organic layer and Water layer re-extracted with 2×25 ml ethyl acetate. The combined organic layers are washed with brinesolution, concentrated under vacuum. The residue was purified by columnchromatography on silica the desired product Bb as a brown solid; yield 85%. ?H NMR(400 MHz DMSO): 8.90 (s 1H), .8.49(m iH), 8.35(m 1H), 7.84-7.80 (m 2H) 4.24(s3H), 2.8(t J = 7.3Hz 2H), 1 .80(m 2H), 0.95(t J = 7.3 Hz 3H). MASS: ESI [M + H] :314.12; Elemental anal. caled. for C15H15N503 C, 57.50; H, 4.83; N, 22.35; 0, 15.32;found C, 57.40; H, 4.85; N, 22.38; 0, 15.37

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; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; SAWANT, Sanghapal Damodar; GINNEREDDY, Lakshma Reddy; MAHESUNI, Srinivas; SYED, Sajad Hussain; DAR, Mohd Ishaq; NARGOTRA, Amit; MAHAJAN, Priya; VISHWAKARMA, Ram Asrey; WO2015/114647; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1018446-95-1, 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. 1018446-95-1, name is tert-Butyl 4-amino-1H-pyrazole-1-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

1-(2-(2-(2-(1H-Pyrazol-4-ylamino)-5-chloropyrimidin-4-yI)ethyl)phenyl)cyclopropanecarboxamide (19) A solution of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.070 g, 0.21 mmol) and teit-butyl 4- amino-i H-pyrazole-1-carboxylate (0.11 g, 0.63 mmol) was stirred in MeOH : water (10:1 ratio, 4 mL) at 70 00 for 2 hours and then at 90 00 for 16 hours. The volatiles were removed in vacuo and the residue was purified by silica gel column chromatography (Combiflash Rf, 0-15% MeOH in DCM) to give the title compound 19 as a light yellow solid (0.015 g, 19%). 1H NMR (300 MHz, d6-DMSO) O 0.93- 1.02(m, 2H), 1.38- 1.49 (m, 2H), 3.04-3.16 (m, 4H), 6.03 (brs, 1H), 6.98 (brs, 1H), 7.18-7.39 (m, 4H), 7.48-7.72 (m, 1H), 7.79-8.00 (m, 1H), 8.37 (5, 1H), 9.62 (5, 1H). LCMS-C: rt 4.92 mm; m/z 383 [M+H].

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 4-amino-1H-pyrazole-1-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; FOITZIK, Richard Charles; MORROW, Benjamin Joseph; HEMLEY, Catherine Fae; LUNNISS, Gillian Elizabeth; CAMERINO, Michelle Ang; GANAME, Danny; STUPPLE, Paul Anthony; LESSENE, Romina; KERSTEN, Wilhelmus Johannes Antonius; HARVEY, Andrew John; HOLMES, Ian Peter; WO2014/26243; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 92933-47-6, name is 5-Isopropyl-1H-pyrazole-3-carboxylic acid, 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 92933-47-6, COA of Formula: C7H10N2O2

Preparation 6 5-ISOPROPYL-1 H-PVRAZOLE-3-CARBOXYLIC acid ethyl ester 5-ISOPROPYL-1 H-PYRAZOLE-3-CARBOXYLIC acid (WO 03/035065, page. 485, example 17b) (1. 00G, 6. 49mmol) was dissolved in a mixture of concentrated sulphuric acid (1.5mL) and ethanol (25mL) and the reaction mixture heated at reflux for 3 hours. The reaction mixture was cooled, poured into water, basified with 0. 88 ammonia then extracted with ethyl acetate. The ethyl acetate was washed with brine, dried over magnesium sulphate and concentrated in vacuo to yield the title product, 514mg (43percent). 1HNMR (CDCI3, 400MHZ) : 1.30 (d, 6H), 1.38 (t, 3H), 3.64 (m, 1H), 4.38 (m, 2H), 6.63 (s, 1 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, 5-Isopropyl-1H-pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/9965; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 5071-61-4, These common heterocyclic compound, 5071-61-4, name is 5-Phenyl-1H-pyrazole-3-carboxylic acid, 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.

Step 2A: Synthesis of N-{4-[(4,6-dimethylpyrimidin-2-yl)({[2- (trimethylsilyl)ethoxy] methyl}) sulfamoyl]phenyl}-3-phenyl-lH-pyrazole-5-carboxamide, 10.2 [00292] HATU (294mg, 0.77 mmol) and DIPEA (0.27 ml, 1.55 mmol) were added at rt to a stirred solution of 4-amino-N-(4,6-dimethylpyrimidin-2-yl)-N-{[2- (trimethylsilyl)ethoxy]methyl}benzene-l-sulfonamide (10.1, 211 mg, 0.52 mmol) in DMF (dry, 15 ml) followed by 5 -phenyl- lH-pyrazole-3-carboxylic acid (97mg, 0.52 mmol). The resulting mixture was stirred at rt for 48h. The solvent was removed in vacuo and the remaining solid was purified by flash column chromatography (heptane/EtOAc 100/0 to 0/100) and triturated from DMSO:CH3CN:water 1 :2: 1 to obtain 63mg (18%) of N-{4-[(4,6-dimethylpyrimidin-2-yl)({[2- (trimethylsilyl)ethoxy]methyl} )sulfamoyl]phenyl } -3 -phenyl- 1 H-pyrazole-5 -carboxamide 10.2 as a pale yellow solid.

Statistics shows that 5-Phenyl-1H-pyrazole-3-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 5071-61-4.

Reference:
Patent; RAZE THERAPEUTICS, INC.; SAIAH, Eddine; (148 pag.)WO2016/40449; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 42098-25-9, 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. 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step C. tert-Butyl [1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl]carbamate A mixture of 5-chloro-1-methyl-4-nitro-1H-pyrazole (0.400 g, 2.48 mmol), tert-butyl azepan-4-yl carbamate (0.58 g, 2.7 mmol), EtOH (3 mL) and DIPEA (1.6 mL, 9.2 mmol) was irradiated in a microwave oven for 1 h at 130 C. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel using CombiFlash apparatus, eluting with EtOAc/hexane (10-60%). The purification gave 0.580 g (69.0% yield) of the sub-title compound as a colorless oil. LCMS calc. for C11H18N5O4 (M+H-t-Bu+H)+: m/z=284.2. found: 284.1.

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-Chloro-1-methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INCYTE CORPORATION; Li, Yun-Long; Burns, David M.; Feng, Hao; Huang, Taisheng; Mei, Song; Pan, Jun; Vechorkin, Oleg; Ye, Hai-Fen; Zhu, Wenyu; Rafalski, Maria; Wang, Anlai; Xue, Chu-Biao; US2015/57265; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics