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. 400755-44-4, name is 1-Ethylpyrazole-3-carboxylic Acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H8N2O2

To 1 -ethyl- 1H- pyrazole-3-carboxylic acid (5.01 g, 35.7 mmol) in benzene/MeOH (45 mL/10 mL) at 0 C was added drop wise (diazomethyl)trimethylsilane (19.7 mL, 39.3 mmol) in hexanes (2M). The cold bath was removed and the reaction mixture was stirred at ambient temperature for one hour. The reaction was quenched with the addition of acetic acid (0.25 mL). The mixture was concentrated under reduced pressure to give crude product, to which was added THF (50 mL) and the solution was cooled to 0 C. Lithium aluminum hydride (1.36 g, 35.7 mmol) was added cautiously to the solution. The cold bath was removed once the addition was complete. The mixture was stirred at ambient temperature for 2 hours and the reaction was quenched by careful addition of sodium sulfate decahydrate. The mixture was filtered through Celite, and the filter pad was washed with EtOAc (200 mL). The filtrate was concentrated under reduced pressure to give the product (4.41 g).

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; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; BRADLEY, Michael; DELISLE, Robert Kirk; HENNINGS, D. David; KENNEDY, April L.; MARMSATER, Fredrik P.; MEDINA, Matthew; MUNSON, Mark C.; RAST, Bryson; RIZZI, James P.; RODRIGUEZ, Martha E.; TOPALOV, George T.; ZHAO, Qian; WO2011/79076; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 10010-93-2, name is 3-Methyl-5-(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 10010-93-2, Formula: C5H5F3N2

To a stirred solution of 5-methyl-3-(trifluoromethyl)-1H-pyrazole (199 mg, 1.328 mmol) in dry acetonitrile (7 mL) at room temp is added sodium hydride (63 mg of a 60% dispersion on mineral oil, 2.66 mmol). The mixture is stirred at room temp for 10 mins after which the initial effervescence had subsided to leave a colourless solution. A solution of trans-trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohexylmethyl ester (Ex. 18 step 1) (400 mg, 1.107 mmol) in dry acetonitrile (4 mL) is then added and the mixture is stirred at room temp for 17 hours. The crude mixture is diluted with water (20 mL) and extracted with EtOAc (3×15 mL). The EtOAc extracts are combined, washed with sat. brine (30 mL), dried (MgSO4), filtered and evaporated to give a mixture of the title compounds as a pale yellow gum. This is used in the next step without further purification.

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

Reference:
Patent; Beattie, David; Colson, Anny-Odile; Culshaw, Andrew James; Sharp, Lisa; Stanley, Emily; Sviridenko, Lilya; US2010/35898; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25016-11-9, name is 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 25016-11-9, COA of Formula: C5H6N2O

A solution of 1-methyl-1H-pyrazole-4-carbaldehyde (2.73 g, 24.80 mmol), (R)-2-methyl-2-propanesulfinamide (3.30 g, 27.30 mmol), and Ti(OiPr)4 (35.2 g, 37.1 mL, 0.124 mol) in THF (60 mL) was stirred with heating on a water bath at 50 C for 20 h. The resulting mixture was poured into water (100 mL) with stirring for 15 min, then filtered and the precipitate was washed twice with DCM. The filtrate was diluted with water (100 mL) and extracted with DCM (20 mL * 3). The combined extracts were dried over K2CO3, filtered through the pad of silica gel, and evaporated under reduced pressure and dried in vacuo to afford pure 2b 5.16 g (97%). = -130.7 (c 1, CHCl3), 1H NMR (400 MHz, CDCl3): delta 8.41 (s, 1H, CH=N), 7.83 (s, 1H, CHpyr), 7.78 (s, 1H, CHpyr), 3.89 (s, 3H, Me), 1.15 (s, 9H, tBu). 13C NMR (100 MHz, CDCl3): delta 154.28, 139.91, 132.14, 119.86, 57.30, 39.29, 22.39 3C. MS (70 eV, EI): m/z (%) = 214 (60) [MH]+, 157 (100), 130 (10), 109 (56), 108 (48), 83 (18), 82 (20), 81 (8), 41 (7). C9H15N3OS (213.3): calcd C 50.68, H 7.09, N 19.70, S 15.03, found C 50.42, H 7.11, N 19.55, S 14.88.

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-Methyl-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kuznetsov, Nikolai Yu.; Khrustalev, Victor N.; Strelkova, Tatyana V.; Bubnov, Yuri N.; Tetrahedron Asymmetry; vol. 25; 8; (2014); p. 667 – 676;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature 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.

General procedure: To a solution of 2-aminobenzamide (1.470 mmol, 1.0 eq.) was added to a solution of Terminal Alkyne (1.470 mmol, 1.0 eq.), Tosyl Azide, (1.470 mmol, 1.0eq.), CuI (0.147 mmol, 0.1 eq.), triethylamine (2.941 mmol, 2.0 eq.), in acetonitrile (10 ml) under N2 atmosphere. The mixture was stirred at room temperature for 12 h. After completion of the reaction (as indicated by TLC) the reaction mixture was poured into water (25 mL) and extracted with ethyl acetate (2×25 mL), dried over Na2SO4, concentrated under vacuum to get crude compound which was purified by column chromatography using a mixture of petroleum ether: ethyl acetate to give the desired product as a white solid.

The synthetic route of 139756-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Srishyalam; Devanna; Basaveswara Rao; Mulakayala, Naveen; Tetrahedron Letters; vol. 58; 30; (2017); p. 2889 – 2892;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1018446-95-1, name is tert-Butyl 4-amino-1H-pyrazole-1-carboxylate, 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 1018446-95-1, name: tert-Butyl 4-amino-1H-pyrazole-1-carboxylate

Intermediate 6 (220 mg, 0.67 mmol), triphosgene (66 mg, 0.22 mmol) and dry THF (5 mE) were sequentially added to a 10 mE three-necked flask. Under nitrogen protection, the reaction mixture was cooled to 00 C., and slowly added with DIPEA (173 mg, 1.34 mmol) dropwise. The reaction mixture was stirred for 10 mm. Then Intermediate 9 (240 mg, 1.34 mmol) was quickly added to the reaction mixture. The reaction mixture was stirred at room temperature overnight, concentrated, and purified by reversed phase column chromatography to give Intermediate 10 (95 mg, 32.4% yield) as a white solid. Because of there is TFA in solution, Intermediate 10 is converted to Compound of Formula Ic during lyophilization.

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, tert-Butyl 4-amino-1H-pyrazole-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; YIN, JIANMING; (11 pag.)US2019/169163; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 16034-46-1, 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. 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 1-methyl-1H-pyrazole-5-carboxylic acid (compound 4A, 1.99 g, 15.8 mmol), DIEA (5.95 g, 46.0 mmol) in CH2Cl2 (20 mL) was added EDCI (5.04 g, 26.3 mmol) and DMAP (1.93 g, 15.8 mmol) at -5 C., the mixture was stirred at -5 C. for 30 min under N2. Then 2-methyl-4-nitroaniline (compound 15, 2.00 g, 13.1 mmol) was added, the mixture was stirred at -5 C. for 30 min, then warmed to 25 C., stirred for 11 hrs. TLC (petroleum ether:ethyl acetate=1:1, Rf=0.55) showed starting material consumed completely. The mixture was concentrated in vacuum to give light yellow oil. The oil was purified by silica gel column chromatograph (petroleum ether:ethyl acetate=100:0 to 50:50) to give 1-methyl-N-(2-methyl-4-nitrophenyl)-1H-pyrazole-5-carboxamide (compound 16, 2.60 g, 76% yield) as light yellow solid.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-pyrazole-5-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Kyn Therapeutics; Castro, Alfredo C.; Evans, Catherine Anne; (108 pag.)US2019/55218; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 31728-75-3, A common heterocyclic compound, 31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H8N2O2, 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.

Under an atmosphere of argon, diisopropylethylamine (3.49 ml) and diphenylphosphoryl azide (2.37 ml) were added in turn to a stirred mixture of 1,5-dimethyl-1H-pyrazole-4-carboxylic acid (1.4 g), tert-butanol (4 ml) and 1,4-dioxane (40 ml) and the reaction mixture was stirred at ambient temperature for 10 minutes. The resultant mixture was heated to 110 C. for 3 hours. The solvent was evaporated and the reaction product was purified by column chromatography on silica using ethyl acetate as the eluent. There was thus obtained 4-(tert-butoxycarbonylamino)-1,5-dimethyl-1H-pyrazole (0.225 g); 1H NMR: (DMSOd6) 1.4 (s, 9H), 2.2 (s, 3H), 3.55 (s, 1H), 6.0 (br s, 1H), 9.3 (br s, 1H).

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; Jung, Frederic Henri; Morgentin, Remy Robert; Ple, Patrick; US2009/76075; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 37687-18-6, These common heterocyclic compound, 37687-18-6, name is 1-(1-Methyl-1h-pyrazol-4-yl)-ethanone, 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.

B. Synthesis of 2-bromo-1-(1-methyl-1H-pyrazol-4-yl)ethanone A solution of 1-(1-methyl-1H-pyrazol-4-yl)ethanone (28.5 g, 230 mmol) in dichloromethane (400 mL) was diluted with absolute ethanol (100 mL) and treated portion-wise with pyridinium tribromide (95%, 77.3 g, 230 mmol). The reaction was stirred at room temperature for 3 hours, during which time it solidified; the mixture was diluted with dichloromethane (300 mL) and water (400 mL), treated with sodium sulfite (5 g) and stirred for 10 minutes. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with water (200 mL), collected by filtration, washed again with water, and dried to afford the product as an off-white solid. Yield: 41.6 g, 205 mmol, 89%. 1H NMR (500 MHz, CDCl3) delta 7.97-7.98 (m, 1H), 7.95 (br s, 1H), 4.17 (s, 2H), 3.95-3.96 (m, 3H).

Statistics shows that 1-(1-Methyl-1h-pyrazol-4-yl)-ethanone is playing an increasingly important role. we look forward to future research findings about 37687-18-6.

Reference:
Patent; Pfizer Inc.; US2012/214791; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1310350-99-2, 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. 1310350-99-2, name is 4-Chloro-1-(difluoromethyl)-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

d) 4-Chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amide A solution of 4-chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid (150 mg, 0.76 mmole) in dichloromethane (5 ml) was subsequently treated at 23 C. with N,O-dimethylhydroxylamine hydrochloride (78 mg, 0.80 mmole), N-methylmorpholine (0.09 ml, 0.8 mmole) and EDCI.HCl (154 mg, 0.8 mmole) and stiffing was continued for 16 h. The mixture was washed with 1 M aqueous HCl and H2O, the organic layer was dried, evaporated and the residue purified by chromatography on silica gel using cyclohexane/AcOEt (2:1) to give the title compound (164 mg) as a colorless oil. MS: m/z=240.1 [M]+.

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-Chloro-1-(difluoromethyl)-1H-pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gabellieri, Emanuele; Guba, Wolfgang; Hilpert, Hans; Mauser, Harald; Mayweg, Alexander V.; Rogers-Evans, Mark; Rombach, Didier; Thomas, Andrew; Woltering, Thomas; Wostl, Wolfgang; US2012/238548; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 942853-22-7, 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. 942853-22-7 name is 1-(2,2,2-Trifluoroethyl)-1H-pyrazole-3-carboxylic acid, 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.

Compound 1029; Starting material Ai (45 mg, 0.056 mmol) is dissolved in 4 N HCI/dioxane and the reaction mixture is for 1 h at RT. The reaction mixture is concentrated in vacuo to give crude Ci. The acid R2i is dissolved in DMF (2.0 mL), DIPEA (0.059 mL, 0.338 mmol) and TBTU (21 .7 mg, 0.068 mmol) are added. The reaction mixture is stirred for 15 mins. The crude Ci is added and the reaction mixture is stirred at RT for 16 h. The reaction mixture is purified by prep HPLC to provide compound 1029. FIA M.S.(electrospray) : 874.4 (M+H)+ Retention time (min) = 6.0 min1H NMR (400 MHz,DMSO-d6): delta 10.83 (s, 1 H) , 8.92 (s, 1 H), 7.95 (b, 1 H), 7.93 (d, 1 H, J = 2.3 Hz), 7.86 (d, 1 H, J = 9.0 Hz), 7.08 (d, 1 H, J = 9.4 Hz), 6.74 (d, 1 H, J = 2.3 Hz), 6.40 (s, 1 H), 5.60 (b, 1 H), 5.44 (m, 1 H), 5.23 (q, 2H, J = 9.3 Hz), 5.09 (b, 1 H), 4.63 (b, 1 H), 4.47 (q, 2H, J = 6.9 Hz), 4.43 (b, 2H), 4.04 (b, 1 H), 3.87 (s, 3H), 2.67-2.65 (m, 1 H), 2.43 (s, 3H), 2.38-2.32 (m, 3H), 2.01 -1 .80 (m, 2H), 1 .58-1 .51 (m, 3H), 1 .44-1 .23 (m, 1 1 H), 1 .39 (t, 3H, J = 7.0 Hz), 0.85 (b, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2,2,2-Trifluoroethyl)-1H-pyrazole-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET , Montse; BORDELEAU, Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63502; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics