pyrazoles-derivatives

Some common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, molecular formula is C14H19N3, 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. HPLC of Formula: C14H19N3

To a solution of 3-tert-butyl-l-p-tolyl-lH-pyrazol-5-amine (102.9 g, 448.9 mmol) in EtOAc (1 L) at 10.9 0C was added a NaOH solution (2.5 M5 269 mL), and the biphasic reaction mixture warmed to 15.9 and then stabilized. Phenyl chloroformate (98.4 g, 156.5 mmol) was added in one portion and the temperature rose to 25.5 and then stabilized. The ice bath was removed and the reaction was monitored by HPLC. After 1 hour an additional 25 mL of 2.5 M NaOH was added. The reaction mixture was stirred overnight, and then diluted with EtOAc (200 mL). The organic layer was washed with brine (1 L)5 dried over Na2SO4 (200 g) and concentrated to about 400 to 500 mL of EtOAc. The concentrated solution was warmed to 60 0C. After the solids had dissolved, heptane (2 L) was slowly added, during which solids formed. After stirring for 30 minutes the solid was collected via filtration and the cake was washed with 400-500 mL of heptane. The cake was dried in a vacuum oven at ambient temperature to yield 156.9 g (95.0%) of the title compound. 1H NMR (400 MHz3 CDCl3) delta 7.39 – 7.31 (m, 6H), 7.26-7.225 (m, 2H), 7.13 (br s, 2H)5 6.96 (br s. IH), 6.47 (br s, IH), 2.42 (s, 3H), 1.34 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 285984-25-0, its application will become more common.

Synthetic Route of 1280210-79-8,Some common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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.

INTERMEDIATE 8; Step A: fert-Butyl 2- { 2-(trimethylsilyl)ethoxy1methyI } -2 , 6-dihvdropwrol o [3 A- c1pyrazole-5(4HVcarboxylateTo a stirred solution of tert~buty 2,6-dihydropyrrolo[3f4~c]pyrazole-5(4H)- carboxylate (20 g, 96 mmol) in DMF (200 mL) at 0 C was added sodium hydride (4.21 g, 105 mmol). After stirring for 1 h at RT, 2-trimethylsilylethoxymethyl chloride (SEM-C1) (4.65 mL, 26.3 mmol) was added. The resulting mixture was stirred at RT overnight. The mixture was quenched with saturated NH4OH, and the solvents were removed. The residue was diluted with ethyl acetate (500 mL), washed with water, brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on a silica gel Biotage 65i column, eluting with 0 to 20% ethyl acetate in hexanes to give the title compound as a colorless gum. LC-MS: 340.1 (M+H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, its application will become more common.

Application of 35691-93-1, A common heterocyclic compound, 35691-93-1, name is Ethyl 3,5-dimethyl-1H-pyrazole-4-carboxylate, molecular formula is C8H12N2O2, 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.

3,5-Dimethyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.10 g, 1 mmol) (prepared as described in Tett 2002, 58, 18, p 3639), 3-bromo-5-trifluoromethyl-pyridine (0.16 g, 1 mmol), copper iodide (0.02 g, 0.2 mmol) and cesium carbonate (1.0 g, 3 mmol) were suspended in DMA (0.5 ml) and heated to 160 C. for 16 h. The reaction was diluted with EtOAc, washed repeatedly with ammonium hydroxide, brine and dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (EtOAc:n-heptane 1:9-2:8 gradient affording the title compound (0.07 g, 35%) as a yellow oil. MS: 314.2 (MH+).

The synthetic route of 35691-93-1 has been constantly updated, and we look forward to future research findings.

Reference of 1260243-04-6, 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. 1260243-04-6 name is Ethyl 5-amino-1H-pyrazole-4-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.

A mixture of ethyl 5-amino-1H-pyrazole-4-carboxylate (546 mg, 3.52 mmol) and 5,5- dimethylhexane-2,4-dione (1 .03 g, 97 % purity, 7.03 mmol) in acetic acid (2.7 ml) was heated for 1 h at 11 OC in a microwave reactor (Biotage In itator). Upon cooling to room temperature, the reaction mixture was portioned between water and dichlormethane and the organic phase was washed with water, filtrated through a silicone filter and concentrated undervacuum. The crude product was purified by flash chromatography (25 g Snap Cartrigde, hexanes/ethyl acetate gradient) to yield the title compound (850 mg, 93% yield). LC-MS (Method 1): R = 1 .25 mm; MS (ESipos) m/z = 262.2 [M+H].1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 1.281 (2.05), 1.299 (4.51), 1.316 (2.11), 1.375(0.78), 1.558 (16.00), 2.619 (8.39), 4.252 (0.66), 4.270 (2.08), 4.288 (2.05), 4.305 (0.61),7.072 (2.38), 8.569 (2.97).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-amino-1H-pyrazole-4-carboxylate, and friends who are interested can also refer to it.

Synthetic Route of 1001020-14-9, The chemical industry reduces the impact on the environment during synthesis 1001020-14-9, name is 3-(Trifluoromethyl)-1H-pyrazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

To a stirred suspension of 3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde (100 mg, 0.609 mmol) and potassium tert-butoxide (137 mg, 1.22 mmol) in THF (3 mL) was added 2-(chloromethyl)-6-methyl-5-phenylthieno[2,3-d]pyrimidin-4(3H)-one (177 mg, 0.609 mmol) and the resultant solution was stirred at RT for 2 days. The reaction mixture was quenched with water and concentrated in vacuo to give the crude product as a beige solid (97 mg, 0.232 mmol, 38%). The material was used 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, 3-(Trifluoromethyl)-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Related Products of 31230-17-8, 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 31230-17-8 as follows.

Example 118a 5-Bromo-1-methyl-3-(5-methyl-1H-pyrazol-3-ylamino)pyridin-2(1H)-one 118a A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1,4-dioxane (15 mL), 5-methyl-1H-pyrazol-3-amine (1 g, 10 mmol) (1), 3,5-dibromo-1-methylpyridin-2(1H)-one (4 g, 15 mmol) (2), and cesium carbonate (6.4 g, 20 mmol). Xantphos (400 mg, 0.8 mmol) and Pd2(dba)3 (700 mg, 0.8 mmol) were added, and the reaction mixture was heated at 100¡ã C. for 5 h. After this time the reaction was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified on flush column eluting with dichloromethane:methanol (20:1) to afford 118a (1.0 g, 35percent). MS: [M+H]+ 283.

According to the analysis of related databases, 31230-17-8, the application of this compound in the production field has become more and more popular.

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. 930-36-9, name is 1-Methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Methylpyrazole

N-methylpyrazole (16.4 g, 200 mmol) and acetic anhydride (38 mL, 400 mmol) were added to the reaction flask.Concentrated sulfuric acid (1 mL, 20 mmol) was added dropwise with stirring, and then reacted under a nitrogen atmosphere at 140 C for 12 h.After the reaction is completed, the system is poured into ice water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and the solvent is removed for column chromatography.(Eluent: Petroleum ether / EtOAc (v/v) = 3/1) afforded 17.7 g of product as a yellow oil. Yield: 71%.

According to the analysis of related databases, 930-36-9, the application of this compound in the production field has become more and more popular.

Related Products of 942853-22-7,Some common heterocyclic compound, 942853-22-7, name is 1-(2,2,2-Trifluoroethyl)-1H-pyrazole-3-carboxylic acid, molecular formula is C6H5F3N2O2, 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.

Intermediate Ck is prepared from Ak by treatment with 4 N HCI/dioxane for 1 h followed by concentration in vacuo. Acid R2i (12.2 mg, 0.063 mmol) is dissolved in DMF (1 ml_), then TEA (29 muIota_, 0.210 mmol) is added followed by TBTU (19.4 mg, 0.060 mmol). The solution is stirred for 15 mins, after which the amine hydrochloride Ck (40 mg, 0.053 mmol) is added in DMF (1 mL). The solution is stirred at RT for 16 h. AcOH is added and the resulting solution is filtered through a Millex filter and purified by prep HPLC (Sunfire column, 0.1% TFA). The pure fractions are combined, frozen and lyophilized to provide compound 1023.FIA M.S.(electrospray) : 900.4 (M+H)+ Retention time (min) = 6.4 min1H NMR (400 MHz,DMSO-d6): delta 10.82 (s, 1H) , 8.94 (s, 1H), 7.96 (d, 1H, J = 7.1 Hz), 7.93 (d, 1H, J = 2.3 Hz), 7.84 (d, 1H, J = 9 Hz), 7.07 (d, 1H, J = 9.4 Hz), 6.74 (d, 1 H, J = 2.3 Hz), 6.40 (s, 1 H), 5.65-5.58 (m 1 H), 5.48-5.43 (m, 1 H), 5.32 (qn, 1 H J = 7.8 Hz), 5.22 (q, 2H, J = 9 Hz), 5.06 (dd, 1H, J = 9.8, 9.4 Hz), 4.63-4.57 (m, 1H), 4.54 (d, 1H, J= 11.8), 4.41 (dd, 1H, J= 7.4, 7.0 Hz), 4.04-4.00 (m, 1H), 3.87 (s, 3H), 2.64-2.58 (m, 2H), 2.43 (s, 3H), 2.38-2.31 (m, 3H), 2.15-2.08 (m, 2H), 2.01-1.98 (m, 1H), 1.85-1.67 (m, 3H), 1.59-1.23 (m, 15H), 0.90-0.86 (m, 2H).

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

Reference of 42098-25-9,Some common heterocyclic compound, 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, molecular formula is C4H4ClN3O2, 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.

Step 1: tert-Butyl 2-(2,6-difluorophenyl)-4-(1-methyl-5-(tert-butyloxycarbonylpyrrolidin-3-yl)-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate 5-Chloro-1-methyl-4-nitro-1H-pyrazole (0.2 g, 1.24 mmol), tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (0.437 g, 1.48 mmol) and aqueous Na2CO3/KOAc solution (1:1, 1.1 M, 1.5 mL) were suspended in MeCN (5 mL). The mixture was degassed under a stream of nitrogen for 5 min. Pd(dppf)2Cl2 (0.1 g, 0.123 mmol) was added and the mixture was heated at 130 C. in a microwave for 90 min. A further portion of Pd(dppf)2Cl2 (50 mg, 0.06 mmol) was added and the mixture was heated at 130 C. for a further 90 min. The solvents were removed under reduced pressure and the crude residue partitioned between EtOAc and water. The organic layer was separated, dried over MgSO4 and concentrated under reduced pressure. The crude product was purified via silica gel column chromatography (40-60% EtOAc/isohexane) to give the intermediate nitro-pyrazole as a yellow oil (76 mg, 21%).

The synthetic route of 42098-25-9 has been constantly updated, and we look forward to future research findings.

7119-95-1, name is 1-Nitropyrazole, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 7119-95-1

A stirred mixture of 1-nitropyrazole (3.45 g, 30.5 mmol) in benzonitrile (33 mL) was heated at 180 ¡ãC for 3 h. The mixture was cooled to rt, diluted with hexane and stirred at rt for 20 min. The precipitated solid was collected by filtration to afford 3-nitro-lH-pyrazole as a tan solid (3.16 g, 91percent). H NMR (300 MHz, DMSO- 6) delta 13.94 (br s, 1H), 8.03 (d, J = 2.4 Hz, 1H), 7.03 (t, J = 2.4 Hz, 1H).

The synthetic route of 7119-95-1 has been constantly updated, and we look forward to future research findings.