Tag: M.W:200-300

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. 75092-30-7, name is 4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 75092-30-7

Step 1. 4-[(4-Fluorophenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid A mixture of 4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid ((Manaev, Yu. A. et al., J. Gen. Chem. USSR (Engl. Transl.), 1982, 52 (11), 2291), 500 mg, 1.98 mmol), 4-fluoroaniline (0.94 ml, 9.90 mmol), copper powder (200 mg) and 5% aqueous sodium carbonate (10 ml) was stirred for 16 h at 100 C. After cooling to room temperature, 2N aqueous sodium hydroxide (100 ml) and diethyl ether (50 ml) were added to the mixture. The mixture was filtered through a pad of Celite. The water layer was separated, washed with diethyl ether (50 ml) and acidified with concentrated hydrochloric acid. The formed precipitate was collected by filtration and dried to give 282 mg (61%) of the title compound as a white solid. Rf value: 0.50 (methanol/dichloromethane/acetic acid=1/10/2 drops). 1H-NMR (DMSO-d6) delta: 7.60 (1 H, s), 7.09-7.05 (4 H, m), 4.01 (3 H, s). Two signals due to NH and CO2H were not observed.

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 75092-30-7.

Reference:
Patent; Kawamura, Kiyoshi; Mihara, Sachiko; Nukui, Seiji; Uchida, Chikara; US2003/130277; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 657428-42-7, 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. 657428-42-7 name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate, 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.

Step D: tert-Butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate A solution of tert-butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate (30.0 kg, 143 mol) in 2-methyltetrahydrofuran (384 mg) was vacuum purged with nitrogen back-fill three times. The, triethylamine (25.0 kg, 247 mol) was added and the batch cooled to -10-5 C. Then, methanesulfonyl chloride (21.4 kg, 187 mol) was slowly added over 2 h. After stirring for 1 h at room temperature, water (150 kg) was added drop-wise at 5-15 C. This was followed by addition of 1N HCl solution until the pH was 7. The resulting layers were separated and the aqueous extracted with 2-methyltetrahydrofuran (106 kg). The combined organics were washed with saturated brine (2*150 kg), dried with Na2SO4, filtered, and concentrated to 60-90 L. The resulting crude was dissolved in 2-methyltetrahydrofuran (381 kg) and charged with a solution of potassium tert-butoxide in THF (805 g in 6.6 kg THF). After stirring 1 h at room temperature under nitrogen, more potassium tert-butoxide in THF (329 g in 3.0 kg THF) was added and stirred for 1 h. Analytical analysis indicates that tert-butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate is the major regioisomer, so saturated brine (154 kg) was then added. After brief agitation, the layers are separated and the oragnics are washed with saturated brine (2*155 kg). The combined aqueous waste layers were then extracted with 2-methyltetrahydrofuran (103 kg). The combined organics were treated with activated carbon (8.75 kg), filtered, and dried with Na2SO4. This was then filtered and concentrated to 60-90 L. This slurry was then heated to dissolve solids at 40-50 C. and n-heptane was added (34 kg). After cooling to room temperature for 2-4 h, n-heptane (156 kg) was added and the slurry was then aged for 2-4 h at 0-5 C. The slurry was filtered and the cake washed with n-heptane. The solids were dried under vacuum at 45-55 C. to give tert-butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Merck Sharp & Dohme Corp; Merck Sharp & Dohme Ltd.; Arroyo, Itzia Z.; Krueger, Davida; Chen, Ping; Moment, Aaron J.; Biftu, Tesfaye; Sheen, Faye; Zhang, Yanfeng; US9181262; (2015); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 916766-83-1, 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. 916766-83-1, name is 3-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a vial containing pinacol ester (200 mg, 0.645 mmol, 1 eq), 3-[4- (chloromethyl)phenyl]-l-methyl-pyrazole (200 mg, 0.97 mmol, 1.5 eq), cesium carbonate (315 mg, 0.97 mmol, 1.5 eq) and Pd(dppf)Cl2 DCM (71 mg, 0.097 mmol, 0.15 eq) were added. The vial was sealed and evacuated under vacuum and purged with N2. THF/H2O solution (5: 1, 5.2 mL total, degassed) was then added via syringe and the resulting solution was stirred at 90 C for 16 h, after which time the reaction mixture was cooled to r.t. and filtered through a plug of Celite with EtOAc and DCM. Solvents were concentrated under reduced pressure, and crude residue was purified by reverse phase HPLC then by normal phase column chromatography (0-70% EtOAc in hexanes to 70-80% EtOAc/DCM) to give the title compound as an off white powder (72 mg, 32%). NMR (400 MHz, CDCI3) d 8.18 (d, J= 2.5 Hz, 1H), 7.78 (d, J= 8.2 Hz, 2H), 7.76 (d, j= 1.3 Hz, 1H), 7.39 (d, j= 2.2 Hz, 1H), 7.36 (s, 1H), 7.15 (d, j= 8.2 Hz, 2H), 6.53 (d, J = 2.3 Hz, 1H), 6.47 (dd, 7= 2.4, 1.9 Hz, 1H), 4.11 (s, 2H), 3.96 (s, 3H), 2.54 (s, 3H). ES-MS [M+H]+ = 355.4

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-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig W.; CONN, P. Jeffrey; ENGERS, Darren W.; ENGERS, Julie L.; BENDER, Aaron M.; LONG, Madeline; (120 pag.)WO2019/241467; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1239726-11-4,Some common heterocyclic compound, 1239726-11-4, name is 1-(2-Fluorophenyl)-5-methoxy-1H-pyrazole-3-carboxylic acid, molecular formula is C11H9FN2O3, 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 example 9Ethyl (S)-3-{[1 -(2-fluoro-phenyl)-5-methoxy-1 H-pyrazole-3-carbonyl]-amino}-3-(2- methyl-phenyl)-propionate Step 1 : 1 -(2-Fluoro-phenyl)-5-methoxy-1 H-pyrazole-3-carbonyl chlorideA suspension of 1 -(2-fluoro-phenyl)-5-methoxy-1 H-pyrazole-3-carboxylic acid (39.1 g, 167 mmol) in 2-methyltetrahydrofuran (300 ml) was cooled to 0 C and DMF (293 muIota, 3.81 mmol) was added. Oxalyl chloride (23.1 g, 182 mmol) was added dropwise. After 16 h at room temperature ca. 100 ml of the solvent were removed by distillation. The resulting suspension of the title compound was used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(2-Fluorophenyl)-5-methoxy-1H-pyrazole-3-carboxylic acid, its application will become more common.

Reference:
Patent; SANOFI; RUF, Sven; PERNERSTORFER, Josef; SADOWSKI, Thorsten; HORSTICK, Georg; SCHREUDER, Herman; BUNING, Christian; OLPP, Thomas; SCHEIPER, Bodo; WIRTH, Klaus; WO2011/92187; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 199678-06-3, 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. 199678-06-3, name is 4-(1-Methyl-1H-pyrazol-4-yl)benzoic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Oxalyl chloride (0.30 g) was added to a suspension of 4-(1-methyl-1H-pyrazol-4-yl)-benzoic acid (0.46 g) in dichloromethane (25 ml). Two drops of dimethylformamide were added and the mixture was stirred for 18 hours at room temperature. The resultant solution was evaporated to dryness to yield the crude acid chloride (0.57 g), which was utilized without further purification.

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, 4-(1-Methyl-1H-pyrazol-4-yl)benzoic acid, other downstream synthetic routes, hurry up and to see.

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

Some common heterocyclic compound, 199678-06-3, name is 4-(1-Methyl-1H-pyrazol-4-yl)benzoic acid, molecular formula is C11H10N2O2, 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. Application In Synthesis of 4-(1-Methyl-1H-pyrazol-4-yl)benzoic acid

EXAMPLE 55 [4-(1-Methyl-1H-pyrazol-4-yl)-phenyl]-(5H,11H-pyrrolo[2,1-c][1,4]-benzodiazepin-10-yl)-methanone Oxalyl chloride (0.30 g) was added to a suspension of 4-(1-methyl-1H-pyrazol-4-yl)-benzoic acid (0.46 g) in dichloromethane (25 ml). Two drops of dimethylformamide were added and the mixture was stirred for 18 hours at room temperature. The resultant solution was evaporated to dryness to yield the crude acid chloride (0.57 g), which was utilized without further purification. The acid chloride was added to a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]-benzodiazepine (0.37 g) and diisopropylethylamine (0.58 g) in dichloromethane (50 ml). After 18 hours at room temperature, the reaction mixture was washed with water and saturated aqueous sodium bicarbonate. The dichloromethane solution was dried over anhydrous sodium sulfate and filtered through a short column of hydrous sodium magnesium silicate and further eluted with several volumes of dichloromethane. The combined organic phase was concentrated on a hot plate with the gradual addition of hexane until crystallization occurred. After cooling, the crystals were collected by filtration to yield the title compound (0.38 g), m.p. 200-201 C.; MS m/z: 368 (M)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 199678-06-3, its application will become more common.

Reference:
Patent; Wyeth; US6511974; (2003); B1;,
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. 153687-35-5, name is 1-(4-Methoxybenzyl)-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., name: 1-(4-Methoxybenzyl)-1H-pyrazole-4-carbaldehyde

1H-PYRAZOLE-4-CARBALDEHYDE (55). To a solution of 1- (4-METHOXY-BENZYL)-1H- pyrazole (0.21 mol) (Synth. Commun. 1990, 20/18 ; 2849) in dry DMF (235 ml) was added POCL3 (1.5 eq. ) dropwise at room temperature. The mixture was then heated at 95C for 16 hrs. After cooling to room temperature, the reaction mixture was neutralized by adding ice and saturated sodium carbonate solution. EtOAc (800 ml) was added and the organic layer was separated and washed several times with water. After drying (Na2SO4), the solvent was removed and the crude product was purified over silica gel to give 16.4 g (35% yield) desired aldehyde 1-(4-METHOXY-BENZYL)-LH- pyrazole-4-carbaldehyde. It was heated with 150 ml TFA for 2 hrs. TFA was evaporated and the basified crude product was purified on silica gel to give 5.3 g of 55.

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 153687-35-5.

Reference:
Patent; IMCLONE SYSTEMS INCORPORATED; WO2005/813; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 51516-68-8,Some common heterocyclic compound, 51516-68-8, name is 5-Amino-1-(3-chlorophenyl)-1H-pyrazole-4-carbonitrile, molecular formula is C10H7ClN4, 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.

General procedure: The experimental procedure was similar to synthesis of analogs1(aei). 5-amino-1-aryl-1H-pyrazole-4-carbonitriles 4(aei)(0.001 mol) were reacted with 2.0 mL of 1,3-diaminopropane andcarbon disulfide (0.004 mol). The temperaturewas 85-95oC and thereaction time was 14-16 hours. The reaction mixture was pouredinto cold water, the precipitate was filtered out and washed withcold water. The reactions were accompanied by means of TLC anddichloromethane as eluent.

The synthetic route of 51516-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Monteiro; Lechuga; Lara; Souto; Vigano; Bourguignon; Calvet; Oliveira; Alves; Souza-Silva; Santos; Pereira; European Journal of Medicinal Chemistry; vol. 182; (2019);,
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. 15001-11-3, name is Ethyl 5-amino-1-(p-tolyl)-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

General procedure: Intermediate 4 (0.001mol) and 5 (0.001mol) were dissolved in pyridine, phosphorus oxychloride is slowly added dropwise under ice bath conditions, then at 40-60C reacted for 5-8h. Finally, the mixture was poured into 30mL saturated Na2CO3 solution and stirred well. After the mixture was acidified, the saturated CuSO4 solution was used to remove pyridine, which greatly improved the purity and yield of the product. The data for compounds 8I-8VI are provided in the supporting information.

The synthetic route of 15001-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 81 – 87;,
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. 73387-52-7, name is 5-(4-Bromophenyl)-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 73387-52-7

5-(4-bromophenyl)-1 -methyl-1 H-pyrazole (7.84 g), sodium te/f-butoxide (3.81 g), 1 ,1 ‘-bus(di-i-propylphosphino)ferrocene (332 mg), and palladium acetate (148 mg ) were placed under nitrogen and combined with 60 ml_ anhydrous 1 ,4-dioxane. The resulting mixture was stirred at room temperature for 1 hour before adding thisopropylsilanethiol (7.81 ml) followed by heating at reflux for 1 hour. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water twice and 5% aqueous sodium chloride once. The organic layer was dried over sodium sulfate, filtered, concentrated, and purified by flash chromatography on silica gel to give the title compound. LCMS (M+H): 347; 1 H NMR (400 MHz, DMSO-c/6) delta ppm 0.85- 0.96 (m, 3 H) 0.96 – 1.02 (m, 18 H) 3.84 (s, 3 H) 7.40 (s, 1 H) 7.46 (s, 1 H) 7.58 (d, J=8.32 Hz, 2 H) 7.63 – 7.71 (m, 2 H).

The synthetic route of 73387-52-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2009/69044; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics