Category: 400755-44-4

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: 400755-44-4, name is 1-Ethylpyrazole-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 400755-44-4, Computed Properties of C6H8N2O2

To a solution of 1 -ethyl- 7/-/-pyrazole-3-carboxylic acid (1 1 1 mg, 0.793 mmol) and diisopropylethylamine (307 mg, 2.379 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 (452 mg, 1 .19 mmol). The reaction mixture was stirred for 20 minutes before a solution of 5-(3-fluorobenzyl)pyridin-2-amine (160 mg, 0.793 mmol) in tetrahydrofuran (1 .0 ml_) was added. The solution mixture was stirred at 20 C for 16 h. The volatiles were removed under reduced pressure and the 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 1 -ethyl-A/-(5-(3-fluorobenzyl)pyridin-2-yl)- 7/-/-pyrazole-3-carboxamide (43.0 mg, 0.132 mmol, 16.7%) as a white solid. 1 H NMR (400 MHz, Dimethylsulfoxide-c/6) d 9.51 (s, 1 H), 8.27 (d, J = 2.0 Hz, 1 H), 8.08 (d, J = 8.5 Hz, 1 H), 7.92 (d, J = 2.3 Hz, 1 H), 7.71 – 7.70 (dd, J = 8.5, 2.2 Hz, 1 H), 7.33 – 7.30 (dd, J = 14.3, 8.0 Hz, 1 H), 7.10 – 7.08 (t, J = 7.0 Hz, 2H), 7.02 – 7.01 (dd, J = 1 1 .9, 5.3 Hz, 1 H), 6.82 (d, J = 2.3 Hz, 1 H), 4.23 – 4.21 (q, J = 7.3 Hz, 2H), 3.95 (s, 2H), 1 .41 – 1 .40 (t, J = 7.3 Hz, 3H).; LCMS (ESI) m/z: 325.1 [M+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, 1-Ethylpyrazole-3-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

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, 400755-44-4, name is 1-Ethylpyrazole-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. Safety of 1-Ethylpyrazole-3-carboxylic Acid

A mixture of 5-(3,5-difluorobenzyl)pyridin-2-amine (0.100 g, 0.45 mmol), 1 -ethyl- 7/-/-pyrazole-3-carboxylic acid (0.053 g, 0.38 mmol), 1 -[b/s(dimethylamino)methylene]- 7/-/-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (0.1 73 g, 0.45 mmol) and A/,A/-diisopropylethylamine (0.147 g, 1 .14 mmol) in anhydrous A/,A/-dimethylformamide (4.00 mL) was stirred at 20 C for 2 h. The reaction solution was extracted with ethyl acetate (20 ml_ x 20). The combined organic layers were washed with water (50 mL) and brine (50 mL) were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude sample was dissolved in minimal A/,A/-dimethylformamide and purified via prep-HPLC (Boston C1 8 21 *250 mm 10 pm column; acetonitrile/0.01 % aqueous trifluoroacetic acid) to give A/-(5-(3,5-difluorobenzyl)pyridin-2-yl)-1 -ethyl- 7/-/-pyrazole-3-carboxamide (0.0304 g, 0.09 mmol, 23%) as a white solid. 1 H NMR (400 MHz, Dimethylsulfoxide-c/6) d 9.68 (s, 1 H), 8.32 (d, J = 1 .8 Hz, 1 H), 8.10 (d, J = 8.5 Hz, 1 H), 7.94 (s, 1 H), 7.79 (dd, J = 8.5, 2.2 Hz, 1 H), 7.13 – 6.95 (m, 3H), 6.85 (d, J = 2.3 Hz, 1 H), 4.26 (q, J = 7.3 Hz, 2H), 3.98 (s, 2H), 1 .44 (t, J = 7.3 Hz, 3H); LCMS (ESI) m/z: 343.1 [M+H]+.

The synthetic route of 1-Ethylpyrazole-3-carboxylic Acid has been constantly updated, and we look forward to future research findings.

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

Reference of 400755-44-4,Some common heterocyclic compound, 400755-44-4, name is 1-Ethylpyrazole-3-carboxylic Acid, molecular formula is C6H8N2O2, 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 242 Production of N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1-ethyl-1H-pyrazole-3-carboxamide Using 1-ethyl-1H-pyrazole-3-carboxylic acid (128 mg, 0.92 mmol), tetrahydrofuran (2.0 mL), N,N-dimethylformamide (20 muL, 0.26 mmol), oxalyl chloride (80 muL, 0.92 mmol), N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (200 mg, 0.61 mmol) and N,N-dimethylacetamide (4.0 mL), and in the same manner as in Example 238, the title compound (111 mg, 40%) was obtained as a white powder. 1H-NMR (DMSO-d6, 300 MHz) delta 0.76-0.85 (4H, m), 1.44 (3H, t, J=7.2 Hz), 1.87-1.97 (1H, m), 4.26 (2H, q, J=7.2 Hz), 6.77 (1H, d, J=2.1 Hz), 7.07 (1H, d, J=9.6 Hz), 7.09-7.16 (1H, m), 7.39 (1H, dd, J=11.4, 8.7 Hz), 7.84 (1H, dd, J=6.5, 2.9 Hz), 7.91-7.96 (2H, m), 8.04 (1H, d, J=9.6 Hz), 9.57 (1H, s), 11.07 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Ethylpyrazole-3-carboxylic Acid, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/137595; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 400755-44-4,Some common heterocyclic compound, 400755-44-4, name is 1-Ethylpyrazole-3-carboxylic Acid, molecular formula is C6H8N2O2, 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 solution of 5-(3-chloro-5-fluorobenzyl)pyridin-2-amine (0.189 g, 0.8 mmol), 1 -ethyl- 7/-/-pyrazole-3-carboxylic acid (0.1 68 g, 1 .2 mmol) and A/,A/-diisopropylethylamine (0.310 g, 2.4 mmol) in A/,A/-dimethylformamide (5 ml_) at room temperature was added 1 -[b/’s(dimethylamino) methylene]- 7/-/-1 ,2, 3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (0.456 g, 1 .2 mmol under nitrogen. The reaction mixture was stirred at 90 C for 3 h. The reaction mixture was diluted with ethyl acetate (80 ml_) and washed with brine (30 ml_ x 3). The combined organic layers were 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. The mobile phase was acetonitrile/10 mM ammonium acetate aqueous solution) to give A/-(5-(3-chloro-5-fluorobenzyl)pyridin-2-yl)-1 -ethyl- 7/-/-pyrazole-3-carboxamide (44.7 mg, 0.13 mmol, 26%) as a pale white solid. 1 H NMR (500 MHz, Dimethylsulfoxide-c/6) d 9.55 (s, 1 H), 8.32 (s, 1 H), 8.1 1 (d, J =8.5 Hz, 1 H), 7.94 (d, J = 2.0 Hz, 1 H), 7.76 (dd, J/ = 1 .5 Hz, J2 = 8.0 Hz, 1 H), 7.25-7.28 (m, 2H), 7.17 (d, J = 9.5 Hz, 1 H), 6.85 (d, J = 2.0 Hz, 1 H), 4.25 (dd, Ji = 7.0 Hz, J2 = 14.5 Hz, 2H), 3.97 (s, 2H), 1 .43 (t, J = 7.0 Hz,3H); LCMS (ESI) m/z: 359.1 [M+H]+.

The synthetic route of 400755-44-4 has been constantly updated, and we look forward to future research findings.