Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 154471-65-5, name is 1-Methyl-3-(trifluoromethyl)-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 154471-65-5, Application In Synthesis of 1-Methyl-3-(trifluoromethyl)-1H-pyrazole

Into a 10-mL sealed tube purged and maintained with an inert atmosphere of argon, was placed a solution of 1-methyl-3-(trifluoromethyl)-1H-pyrazole (10.0 g, 66.62 mmol) and NBS (16.2 g, 66.62 mmol) in DMF (100 mL). The resulting solution was stirred overnight at 50 C. in an oil bath. The reaction was then quenched by the addition of ice water (1 L). The resulting solution was extracted with ether (3×200 mL), the organic layers combined and dried over anhydrous Na2SO4, filtered and then concentrated to provide the desired product as a yellow oil (12.0 g, crude), which was used as is without further purification. 1H NMR (400 MHz, CDCl3): delta 7.46 (s, 1H), 3.94 (s, 3H) ppm.

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

Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 660845-30-7, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C6H5ClF2N2O, 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 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde

5-Chloro-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxylic acid (Example lib) (I la) (Mb)In a 500 mL round-bottom flask, 6.0 g (31 mmol) of 5-chloro-3-(difluoromethyl)-l-methyl-lH- pyrazole-4-carbaldehyde were taken up in 30 mL of toluene. A solution of 2.4 g (62 mmol) of sodium hydroxide in 6 mL of water was added to the reaction mixture, followed by 103 mL of a 30% strength solution of hydrogen peroxide in water. During the addition, the temperature was kept below 37 C. The reaction mixture was then stirred at 50 C for 7 h. After cooling, the organic phase was extracted with 100 mL of water. The aqueous phase was acidified to pH 2 using dilute hydrochloric acid. The white precipitate formed was filtered off, washed twice with 20 mL of water and dried. This gave 3.2 g of 5-chloro-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxylic acid as a white solid.’H NMR (400 MHz, DMSO- 6) delta ppm : 3.78 (s, 3H); 7.12 (t, 1H, JHF= 53.60 Hz); 13.19 (s, IR (KBr): 1688 cm_1 (C=0); 2200-3200 cm”1 broad;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 660845-30-7, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AG; BENTING, Juergen; COQUERON, Pierre-Yves; CRISTAU, Pierre; DAHMEN, Peter; DESBORDES, Philippe; DUBOST, Christophe; GARY, Stephanie; GREUL, Joerg; HADANO, Hiroyuki; VORS, Jean-Pierre; WACHENDORFF-NEUMANN, Ulrike; WO2012/65947; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application 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 stirred solution of 4-bromo-pyrazole (10.44 g, 71.03 mmol) in anhydrous DMF (96 mL), cooled to 0C, was slowly added NaH (60% in mineral oil) (3.13 g, 78.133 mmol). The solution was stirred for 1 hour at 0C. 4-Methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (19.82 g , 71.03 mmol) was added slowly and the reaction was heated to 100C overnight or until consumption of the pyrazole by NMR. The reaction was cooled to room temperature and water added (20 mL) followed by extraction with EtOAc. The combined extracts were washed with saturated aqueous NaCI (4 x 20 mL), dried with Na2SO4 and concentrated to afford 4-(4-bromo-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester as an orange oil. The oil was purified using silica gel chromatography eluting with 10% EtOAc/hexanes to 25% EtOAc/hexanes to provide 4-(4-bromo-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester as a white solid (10.55 g, 45% yield) with a R^= 0.4 (25% EtOAc/hexanes, using iodine as the stain). 1H NMR (CDCI3, 400 MHz) 8 7.46 (s, 1H), 7.43 (s, 1H), 4.23 (m, 3H), 2.88 (m, 2H), 2.10 (m, 2H), 1.88(m, 2H), 1.47(s, 9H).

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; PFIZER INC.; WO2006/21881; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 4149-06-8,Some common heterocyclic compound, 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, molecular formula is C9H9N3O, 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: To a mixture of 3-amino-1-phenyl-2-pyrazolin-5-one 1 (0.35 g, 2 mmol), dimedone 2 (0.28 g, 2 mmol), and aldehyde 3 (2 mmol) in 15 mL ethanol, 0.14 g (0.004 mol %) H3PW12O40 was added. The reaction mixture was refluxed at 80 C for the time reported in Table 1. Reaction progress was monitored by TLC using EtOAc-hexane (60:40) as eluent. After reaction completion, 50 mL cold water was added to the reaction mixture. The crude product was recrystallized using methanol to obtain the pure product.

The synthetic route of 4149-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zahedifar, Mahboobeh; Shojaei, Reza; Sheibani, Hassan; Research on Chemical Intermediates; vol. 44; 2; (2018); p. 873 – 882;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 25016-20-0, 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 25016-20-0 as follows.

To a solution of 1 -methyl- 7/-/-pyrazole-3-carboxylic acid (50 mg, 0.397 mmol) and diisopropylethylamine (154 mg, 1 .19 mmol) in tetrahydrofuran (4.0 ml_) at 20 C was added 1 -[b/s(dimethylamino)methylene]- 7/-/-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (226 mg, 0.595 mmol). The reaction mixture was stirred for 20 minutes before a solution of 3-((6-aminopyridin-3-yl)methyl)-5-fluorobenzonitrile (90 mg, 0.397 mmol) in tetrahydrofuran (1 .0 mL) was added. The reaction solution was stirred at 20 C for 16 h. The volatiles were removed under reduced pressure and the crude residue was added to a mixture of dichloromethane (50 mL) and water (50 mL). The combined organic layers were collected, dried over sodium sulfate, filtered and concentrated. The crude sample was dissolved in minimal A/,A/-dimethylformamide and purified via prep-HPLC (Boston C18 21 *250 mm 10 pm column; acetonitrile/0.01 % aqueous trifluoroacetic acid) to give A/-(5-(3-cyano-5-fluorobenzyl)pyridin-2-yl)-1 -methyl- 7/-/-pyrazole-3-carboxamide as a white solid (29.3 mg, 0.087 mmol, 22%). 1 H NMR (400 MHz, Dimethylsulfoxide-c/e) d 1 0.48 (s, 1 H), 8.41 (s, 1 H), 8.32 (d, J = 1 .8 Hz, 1 H), 8.10 (d, J = 8.9 Hz, 2H), 7.77 – 7.66 (m, 2H), 7.57 (d, J = 9.4 Hz, 1 H), 4.02 (s, 2H), 3.87 (s, 2H); LCMS (ESI) m/z: 336.1 [M+H]+.

According to the analysis of related databases, 25016-20-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, 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. Recommanded Product: 1260243-04-6

To a mixture of ethyl 5-amino- lH-pyrazole-4-carboxylate (150.00 g, 1.08 mmol) and ethyl (E)-3-ethoxyprop-2-enoate (292.16 g, 2.03 mol) in DMF (3.2 L) was added Cs2C03 (656.77 g, 2.02 mol) in one portion at 20 °C under N2. The mixture was stirred at 110 °C for 6 h. TLC (PE: EtOAc=l : 1) showed the reaction was completed. The mixture was cooled to 20 °C and filtered through a celite pad. The filter cake was washed with ethyl acetate (3X30 mL). The filtrate was added to H20 (2 L) and acidified with HOAc to pH=4. The resultant precipitate was filtered to afford A-1-7 (173.00 g, 834.98 mmol, 86.36percent yield) as a white solid: 1H NMR (400 MHz, DMSO-d6) delta 8.54 (d, 7=7.91 Hz, 1H), 8.12 (s, 1H), 6.13 (d, 7=7.91 Hz, 1H), 4.27 (q, 7=7.11 Hz, 2H), 1.28 (t, 7=7.09 Hz, 3H).

The synthetic route of Ethyl 5-amino-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TP THERAPEUTICS, INC.; CUI, Jingrong J.; LI, Yishan; ROGERS, Evan W.; ZHAI, Dayong; DENG, Wei; UNG, Jane; (170 pag.)WO2017/4342; (2017); 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 113100-53-1 as follows. Computed Properties of C6H5F3N2O2

EXAMPLE 1 This Example illustrates the preparation of 1-methyl-3-trifluoromethyl-1 H-pyrazole-4- carboxylic acid (theta-dichloromethylidene-benzonorbornene-S-yOamide (compound A-1.4):theta-Dichloromethylene-S-amino-benzonorbomene (175 mg, 0.729 mmol, prepared as described in Example 6) in dichloromethane (10ml) was reacted with 1-methyl-3- trifluoromethyl-1 H-pyrazole-carboxylic acid (170mg, 0.874 mmol, 1.2 eq.) in the presence of bis-(2-oxo-3-oxazolidinyl)-phosphinic acid chloride (278 mg, 1.09 mmol, 1.5 eq.) and triethylamine (184 mg, 1.821 mmol, 2.5 eq.) at ambient temperature under stirring for 23 hours. The reaction mixture was extracted with saturated sodium bicarbonate solution and saturated brine, dried over Na2SO4 and purified on silica gel in ethyl acetate-hexane-(1 :1). 210 mg (69% of theory) of i-methyl-S-trifluoromethyl-I H-pyrazole^-carboxylic acid (9- dichloromethylidene-benzonorbornene-5-yl)amide (compound A-1.4, m.p. 179-181 0C) was obtained.

According to the analysis of related databases, 113100-53-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2008/131901; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, molecular formula is C5H9N3, 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. Recommanded Product: 3524-32-1

General procedure: A solution of equimolar amounts (4.5 mmol) of 1,3-dimethyl-1H-pyrazol-5-amine 3 [18] and substituted phenylisocyanates 4a-g in THF (12 mL) was stirred at room temperature for 24 h. The solid residue was filtered, washed with 1 mL of ethyl acetate, and then crystallized from a suitable solvent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3524-32-1, its application will become more common.

Reference:
Article; Raimondi, Maria Valeria; Maggio, Benedetta; Raffa, Demetrio; Plescia, Fabiana; Cascioferro, Stella; Cancemi, Gabriella; Schillaci, Domenico; Cusimano, Maria Grazia; Vitale, Maria; Daidone, Giuseppe; European Journal of Medicinal Chemistry; vol. 58; (2012); p. 64 – 71;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 16209-00-0, 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 16209-00-0 as follows.

EXAMPLE 58 [4-(Pyrazol-1-yl)-phenyl]-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone To a suspension of 4-(pyrazol-1-yl)benzoic acid (1.56 g) in dichloromethane (25 ml) was added oxalyl chloride (1.04 g) and one drop of dimethylformamide.. The mixture was stirred at room temperature for 18 hours to yield a clear solution.. The volatile material was removed under reduced pressure to afford 4-(pyrazol-1-yl)benzoyl chloride as a pale yellow solid (1.58 g), which was utilized without further purification.

According to the analysis of related databases, 16209-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; EP1000062; (2004); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 2075-46-9, A common heterocyclic compound, 2075-46-9, name is 4-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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.

[0214j A mixture of 2-bromoethanol (3.75 g, 30.00 mmol), 4-nitropyrazzole (3.39 g, 30.00 mmol) and K2C03 (4.97 g, 36.00 mmol) in acetonitrile (30 mL) was refluxed for 16 h. Then the mixture was filtered and the filtrate was concentrated to dryness to give crude product 2-(4-nitro-1H-pyrazol-1-yl)ethanol as a white solid (4.70 g, yield: 100%), which was used directly in the next step. ESI-MS (M+H) : 158.0.

The synthetic route of 2075-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics