Month: October 2020

A common compound: 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic acid, belongs to pyrazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 3112-31-0

A.5-[(R)-2-Biphenyl-4-yl-1-(1-carboxy-cyclopropylmethyl)-ethylcarbamoyl]-2H-pyrazole-3-carboxylic acid (R7=H)3,5-Pyrazoledicarboxylic acid (35.2 mg, 226 mumol, 1.0 eq.), DIPEA (126 muL) and HATU (85.9 mg, 226 mumol, 1.0 eq.) and DCM (5 mL) were combined and stirred for 5 minutes at room temperature. 1-((R)-2-Amino-3-biphenyl-4-yl-propyl)-cyclopropanecarboxylic acid (86.7 mg, 294 mumol, 2.3 eq,) and DIPEA (0.5 mL) in DCM (5 mL) was added, and the resulting mixture was stirred for 1 hour.The reaction was quenched with saturated aqueous NH4Cl and the product was extracted with DCM, dried and evaporated.The resulting product was combined with AcOH (1.5 mL) and purified with preparative HPLC to yield the title compound (21.4 mg; 93percent purity). MS m/z [M+H]+ calc’d for C24H23N3O5, 434.16; found 433.5.

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, 3112-31-0, other downstream synthetic routes, hurry up and to see.

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. 3524-32-1 name is 5-Amino-1,3-dimethylpyrazole, 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. 3524-32-1

A) 4-Bromo-1,3-dimethyl-1H-pyrazol-5-amine To a solution of 1,3-dimethyl-1H-pyrazol-5-amine (8.77 g) in ethyl acetate (180 mL), N-bromosuccinimide (14.75 g) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours in a nitrogen atmosphere. The reaction mixture was diluted with a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to obtain the title compound (12.6 g). MS: [M+H]+ 189.9

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-1,3-dimethylpyrazole, and friends who are interested can also refer to it.

A common heterocyclic compound, 1203705-55-8, name is 3-Bromo-1H-pyrazol-5-amine, molecular formula is C3H4BrN3, 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. 1203705-55-8.

Methyl 2-(2-bromo-7-hydroxy-5-methylpyrazolo / ,5-aj ‘pyrimidin-6-y I) acetate.; To a solution of 3-bromo-lH-pyrazol-5-amine (0.2 g, 1.235 mmol) and dimethyl 2- acetylsuccinate (0.697 g, 3.70 mmol) in xylene (10 mL) was added -toluenesulfonic acid monohydrate (2 mg, 10.51 muiotaetaomicron). The reaction mixture was heated at reflux under a Dean-Stark trap for 8 h. The solid was filtered and washed with hexanes to afford the title compound (0.201 g, 54.2%). ? NMR (400 MHz, MeOD) delta ppm 2.37 (3 H, s), 3.65 (2 H, s), 3.71 (3 H, s), 6.20 (1 H, s).

The synthetic route of 3-Bromo-1H-pyrazol-5-amine has been constantly updated, and we look forward to future research findings.

52222-73-8, The chemical industry reduces the impact on the environment during synthesis 52222-73-8, name is 4-(Trifluoromethyl)-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Step A: 5-nitro-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidine To a solution of 2-chloro-5-nitropyrimidine (1.5 g, 9.4 mmol) and 4-(trifluoromethyl)-1H-pyrazole (1.41 g, 10.3 mmol) in acetonitrile (40 mL) was added potassium carbonate (2.60 g, 18.8 mmol). The reaction was heated to 80 C. and stirred overnight. The reaction was concentrated and the residue was diluted with water and extracted with ethyl acetate (2*40 mL). The combined organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography gave 5-nitro-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidine (1.5 g, 62%) as a yellow solid. 1H NMR (400 MHz, CDCl3, delta): 9.48 (s, 2H), 8.92 (s, 1H), 8.05 (s, 1H).

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

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 35100-92-6 as follows. 35100-92-6

4 – ((2,5-dichloro-4-yl) amino) -3-ethyl piperidine-1-carboxylate (0.27g, 0.71mmol) in anhydrous 1,4-dioxane was suspended inSix rings (6.0mL), to which was added 1,5-dimethyl -1H- pyrazol-3-amine (0.16g, 1.44mmol), palladium acetate (32mg, 0.14mmol), BINAP (90mg, 0.14mmol) and cesium carbonate (0.47g, 1.43mmol). The reaction mixture was placed in a sealed tube, exhausted systemAir, refilled with nitrogen repeatedly, and then the reaction was heated to 150 deg.] C, reacted for 2 hours under microwave irradiation. The reaction mixture was reducedPressure concentrated. The resulting residue was purified by silica gel column chromatography (DCM / 3M solution of NH3 in MeOH (v / v) = 100/1 to 50/1 to 30/1 to 10/1)Purified to give 4 – ((5-chloro-2 – ((1,5-dimethyl–1H- pyrazol-3-yl) amino) pyrimidin-4-yl) amino) -3-ethylpiperidine – 1- carboxylate as a yellow solidBody (0.19g, 60% yield) and 4 – ((2 – ((1,5-dimethyl–1H- pyrazol-3-yl) amino) pyrimidin-4-yl) amino) -3-ethyl piperidine-1-carboxylic acid tert-butylEster as a brown solid (0.20g, crude yield 67%, non-pure).

According to the analysis of related databases, 35100-92-6, the application of this compound in the production field has become more and more popular.

10250-64-3, Adding a certain compound to certain chemical reactions, such as: 10250-64-3, name is 1-Methyl-3-phenyl-1H-pyrazole-5-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 10250-64-3.

A mixture of HATU (0.5593 g, 1.471 mmol), DIPEA (0.7066 ml, 4.045 mmol), N- (2-aminoethyl) -4-ethoxybenzamide hydrochloride (0.300 g, 1.226 iranol) and l-methyl-3-phenyl-lH-pyrazole-5- carboxylic acid (0.2479 g, 1.226 mmol) in THF (15 mL) was stirred at room temperature overnight. The mixture was quenched with water (150 ml) and the solid filtered, dried on high vacuum and purified on silica gel by eluting with 75% EtOAc/Hex. The pure material was recrystallized from EtOAc/hexanes to give N- (2- (4-ethoxybenzamido) ethyl) -1-methyl- 3-phenyl-lH-pyrazole-5-carboxamide (0.145 g, 30%) as a white solid: 1H NMR (400 MHz, DMSOd6) delta 1.33 (t, J = 7.0 Hz, 3H), 3.42 (br, 4H), 4.05-4.10 (m, 5H), 6.97 (d, J = 8.8 Hz, 2H), 7.23 (s, IH), 7.32 (t, J = 7.3 Hz, IH), 7.43

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 3469-69-0 as follows. 3469-69-0

Step 1: 1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole 4-Iodo-1H-pyrazole (3.0 g) was suspended in benzene (150 mL) and the suspension was heated while stirring. Ethyl vinyl ether (4.4 mL) was added thereto, concentrated HCl was added dropwise thereto, and the resulting mixture was stirred at 60 C. for 3 hours. After completion of the reaction, the resulting mixture was concentrated by evaporation under a reduced pressure, and the residue was neutralized using aqueous saturated sodium hydrogen carbonate (10 mL). The resulting mixture was extracted with ethyl acetate (50 mL) and the extract was washed successively with distilled water (100 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated by evaporation under a reduced pressure. The resulting residue was purified by silica gel chromatography to obtain the title compound as a transparent yellow liquid (3.0 g, yield 73%). 1H NMR (CDCl3): delta 7.54 (s, 1H), 7.41 (s, 1H), 5.40 (q, 1H, J=6.0 Hz), 3.38-3.18 (m, 2H), 1.54 (d, 3H, J=6.0 Hz), 1.05 (t, 3H, J=7.1 Hz).

According to the analysis of related databases, 3469-69-0, the application of this compound in the production field has become more and more popular.

518990-21-1, These common heterocyclic compound, 518990-21-1, name is Ethyl 1,4,6,7-tetrahydropyrano[4,3-c]pyrazole-3-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.

The crude 1,4,6,7-tetrahydropyrano[4,3-c]pyrazole-3-carboxylic acid ethyl ester (3) (915 g) was dissolved in ethanol (1.8 L).An aqueous solution (3.6 L) of lithium hydroxide (424 g, 11 mol, 2.2 eq.) was slowly added dropwise at a temperature of 10-20 C.After the completion of the dropwise addition, the temperature was raised to 50 C, and the reaction was carried out for 2-3 h. The reaction was confirmed by TLC.After concentrating the reaction mixture, the pH was adjusted to 1-2 with dilute hydrochloric acid at 10-20 C, and a white solid precipitated.Stir for 30 min, filter, wash with water (900 mL * 2), dry,A white powder of 547 g was obtained in a yield of 65% and a UPLC purity of 99%.

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 518990-21-1.

The chemical industry reduces the impact on the environment during synthesis 54605-72-0, name is 1-Phenylpyrazole-4-carboxaldehyde, I believe this compound will play a more active role in future production and life. 54605-72-0

General procedure: An oven-dried 3-neck round-bottomed ask equipped with amagnetic stir bar was charged with aryl aldehyde (1.0 equiv.) andtriphenylphosphine (1.2 or 1.5 equiv.). The system was sealed withthree PFTE septa, and subsequently evacuated and backlled withN2 three times. Dry NMP was added via syringe transfer (PTFE sy-ringe with oven-dried stainless-steel needle), and the system wasimmersed in a preheated 100C oil bath. Once no solid reagentsremained (approximately 2 min of heating), potassium bromodi-uoroacetate (1.5 or 1.8 equiv.) was added portionwise over 0.5 h,with the rate of addition controlling the evolution of CO2 gas. Onceall of the potassium bromodiuoroacetate was added, the solutionwas allowed to stir for 0.5e1 h. Upon completion, the reaction wascooled to room temperature and then quenched with H2O. Subse-quently, Et2O was added to the reaction, and the mixture waswashed with H2O (ve times), and the aqueous layer was back-extracted with Et2O (two times). The combined organic layerswere dried over Na2SO4 and concentrated. The crude material wasdry-packed onto silica gel and then eluted through a plug of silicagel with EtOAc:hexanes (1:1) to remove triphenylphosphine oxide.Subsequently, H2O2 (30% in H2O) was added to the mother liquorand allowed to react for 30 min to oxidize the residual triphenyl-phosphine. The organic layer was washed with H2O (three times),dried over Na2SO4, concentrated, and subjected to normal phaseash chromatography using EtOAc and hexanes.

The chemical industry reduces the impact on the environment during synthesis 54605-72-0. I believe this compound will play a more active role in future production and life.

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. 26308-42-9, name is 3-Ethyl-1-methyl-1H-pyrazole-5-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 26308-42-9

Example 306 Production of N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-methylphenyl]-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide In the same manner as in Example 259 and using 3-ethyl-1-methyl-1H-pyrazole-5-carboxylic acid (120 mg, 0.80 mmol), tetrahydrofuran (5 mL), N,N-dimethylformamide (1 drop), oxalyl chloride (170 muL, 2.0 mmol), N-[6-(3-amino-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (200 mg, 0.62 mmol) and N,N-dimethylacetamide (7 mL) as starting materials, the title compound (190 mg, 68%) was obtained as a white solid. 1H-NMR (DMSO-d6, 300 MHz) delta 0.73-0.86 (4H, m), 1.19 (3H, t, J=7.8 Hz), 1.87-1.97 (1H, m), 2.25 (3H, s), 2.57 (2H, q, J=7.8 Hz), 3.99 (3H, s), 6.85 (1H, s), 7.04 (1H, d, J=9.5 Hz), 7.10 (1H, d, J=8.3 Hz), 7.27 (1H, s), 7.35 (1H, d, J=8.3 Hz), 7.94 (1H, s), 8.03 (1H, d, J=9.5 Hz), 9.81 (1H, s), 11.06 (1H, s).

The synthetic route of 26308-42-9 has been constantly updated, and we look forward to future research findings.