Day: July 31, 2021

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. 3463-30-7, name is 1-(4-Nitrophenyl)-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H7N3O2

2 (2.0 g, 10.15 mmol), MeOH (40 mL). Pd/C (1.0 g). RT, hydrogen balloon pressure, 16h. Purification afforded 1.5 g of 3.of

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 3463-30-7.

Reference:
Patent; UNITHER VIROLOGY, LLC; RAMSTEDT, Urban; WARFIELD, Kelly Lyn; TRESTON, Anthony; (147 pag.)WO2016/73652; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1239363-40-6, name is 1-Cyclopropyl-4-iodo-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. Product Details of 1239363-40-6

Intermediate 10: To a stirred solution of Intermediate 1OA (460 mg, 1.965 mmol) in THF (5 mL) at 0 C was added iPrMgCl (1.08 1 mL, 2.162 mmol) quickly. After 30 mm, additional 0.15 eq of iPrMgCl was added and after 30 mm, the mixture was cooled to -78 C. N-Methoxy-N-methylacetamide (304 mg, 2.95 mmol) was added quickly andthe reaction was warmed to RT for 3h. The reaction mixture was concentrated in vacuo and diluted with EtOAc. The organic layer was washed with H20. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified to give Intermediate 10 (250mg, 1.665 mmol, 85% yield) as a clear liquid. LCMS Anal. Calc?d for C8H,0N20 150.8, found [M+H] 151.0.

The synthetic route of 1-Cyclopropyl-4-iodo-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MENG, Wei; ZHAO, Guohua; WO2015/134701; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 5932-27-4, These common heterocyclic compound, 5932-27-4, name is Ethyl 1H-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.

1 – ( [2-(trimethylsilyl)ethoxy]methyl) – lH-pyrazole-3 -carbaldehyde was prepared as follows: 3-Methyl pyrazole (50 g, 0.61 mol) was placed in a 5 L round-bottom flask equipped with mechanical stirrer. 3 L of water was added and heated to 80 C. KMn04 (211.90 g, 1.34 mol) was added portion wise and refluxed for 4.5 h. After stirring at rt overnight, solid was filtered and washed with water. The water was removed in vacuo and 100 mL of water was kept in the flask which was acidified with 1 N HCl to pH 4. It was extracted with EtOAc (2x 1L), washed with brine (2×150 mL), dried over MgS04, filtered and removed in vacuo to yield 1H-pyrazole-3-carboxylic acid (38 g, 56percent) as a white solid. 38 g (0.34 mol) of IH-pyrazole-3-carboxylic acid was refluxed in anhydrous ethanol (1 L) and conc. sulfuric acid (60 mL) for 20 h under nitrogen. Ethanol was removed and crude was basified to pH 8. Precipitated solid was filtered. The filtrate was extracted with THF/CHC13 (2: 3, 3x 1 L), dried over MgS04, filtered and removed in vacuo to yield ethyl 1H-pyrazole-3- carboxylate (39 g, 82percent) as a white solid. To a suspension of ethyl 1H-pyrazole-3-carboxylate (4.42 g, 31.57 mmol) in 1,4-dioxane (140 mL) under N2 atmosphere at 0 C was added NaH (0.91 g, 37.88 mmol) and stirred for 15 min. Neat SEM-Cl (5.79 g, 34.73 mmol) was added drop wise to reaction mixture and stirred overnight at rt. It was quenched with water (30 mL) and excess 1,4-dioxane was removed in vacuo. The residue was extracted with EtOAc (2×250 mL), washed with water (1×50 mL), dried over MgS04, filtered and removed in vacuo to give crude ethyl 1 – {[2- (trimethylsilyl)ethoxy]methyl}-1H pyrazole-3-carboxylate (8.84 g) as a yellow oil. The crude material was used in next step without purification. To a suspension of LiAlH4 in THF (100 mL) at 0 C under N2 atmosphere was added a solution of ethyl 1- f [2-(trimethylsilyl)ethoxy]methyl}-1H pyrazole-3-carboxylate (8.88 g, 32.88 mmol) slowly. After addition was completed the cooling bath was removed and reaction mixture was stirred overnight. It was quenched with water (10 mL) carefully at 0 C. THF was removed and residue was diluted with DCM (250 mL) and organic layer was separated, dried over MgS04 and removed in vacuo. The crude material was plugged thru a pad of silica gel with EtOAc/hexanes (from 10percent to 100percent) to yield (1-{[2- (trimethylsilyl)ethoxy]methyl) -lH-pyrazol-3-yl)methanol (5.80 g, 77percent) as an yellow oil. 53.75 g (0.24 mol) of (1- f [2-(trirnethylsilyl)ethoxy]methyl}-1H pyrazol-3-yl)methanol was dissolved in THF and 122.97 g (1.41 mol) of Mn02 was added. The resulting mixture was refluxed for 60 h. Solid material was filtered through a pad of celite and washed with hot THF. The filtrate was removed in vacuo to give crude product. The crude was plugged thru a pad of silica gel and eluted with EtOAc/hexanes (from 20percent to 50percent) to yield 1-{[2- (trimethylsilyl)ethoxy]methyl}-1H pyrazole-3-carbaldehyde (50.88 g, 86.5percent) as a red oil.

Statistics shows that Ethyl 1H-pyrazole-3-carboxylate is playing an increasingly important role. we look forward to future research findings about 5932-27-4.

Reference:
Patent; ASTRAZENECA AB; WO2005/111001; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 96799-02-9, name is 5-(Furan-2-yl)-1H-pyrazol-3-amine, 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 96799-02-9, Recommanded Product: 96799-02-9

Example 6 8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid (5-furan-2-yl-1H-pyrazol-3-yl)-amide This compound was prepared from 8-(4Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride (Reference Example 1) and commercially available 5-furan-2-yl-1H-pyrazol-3-ylamine (Maybridge) as prepared in example 1, yielding a yellow solid. MS (M+H) m/z=420.

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, 5-(Furan-2-yl)-1H-pyrazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/110745; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 10199-57-2, These common heterocyclic compound, 10199-57-2, name is 5-Methyl-1-phenyl-1H-pyrazole-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.

Example 74 Production of N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-5-methyl-1-phenyl-1H-pyrazole-3-carboxamide Using 5-methyl-1-phenyl-1H-pyrazole-3-carboxylic acid (196 mg, 0.97 mmol), tetrahydrofuran (2.0 mL), N,N-dimethylformamide (30 muL, 0.39 mmol), oxalyl chloride (85 muL, 0.97 mmol), N-[6-(4-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (200 mg, 0.65 mmol) and N,N-dimethylacetamide (4.0 mL), and in the same manner as in Example 255, the title compound (223 mg, 70%) was obtained as a white powder. 1H-NMR (DMSO-d6, 300 MHz) delta 0.76-0.83 (4H, m), 1.86-1.96 (1H, m), 2.31 (3H, s), 6.85 (1H, s), 7.02 (1H, d, J=9.6 Hz), 7.23 (2H, d, J=9.3 Hz), 7.36-7.46 (5H, m), 7.71 (2H, J=9.3 Hz), 7.92 (1H, s), 8.01 (1H, d, J=9.6 Hz), 10.62 (1H, s), 11.05 (1H, s).

Statistics shows that 5-Methyl-1-phenyl-1H-pyrazole-3-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 10199-57-2.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/137595; (2009); 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 1621-91-6 as follows. Formula: C4H4N2O2

b) Methyl lH-pyrazole-3-carboxylate lH-Pyrazole-3-carboxylic acid (15 g, 133.8 mmol) was dissolved in MeOH (250 ml). Concentrated H2S04 (30 ml) was added to the solution. The resulting mixture was refluxed for 12 h and concentrated. The residue obtained was quenched by saturated aqueous solution of NaHC03 and extracted with EtOAc. The organic layer was concentrated. Yield 12.05 g. 1H-NMR (400 MHz; CDC13): delta 3.98 (s, 3H), 6.86 (d, 1H), 7.85 (d, 1H), 1 1.9 (bs, 1H).

According to the analysis of related databases, 1621-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORION CORPORATION; TOeRMAeKANGAS, Olli; WOHLFAHRT, Gerd; SALO, Harri; RAMASUBRAMANIAN, Rathna, Durga; PATRA, Pranab, Kumar; MARTIN, Arputharaj, Ebenezer; HEIKKINEN, Terhi; VESALAINEN, Anniina; MOILANEN, Anu; KARJALAINEN, Arja; WO2012/143599; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 478968-48-8, The chemical industry reduces the impact on the environment during synthesis 478968-48-8, name is Ethyl 3-methoxy-1H-pyrazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

To a suspension of ethyl 3-methoxy-1H-pyrazole-4-carboxylate (350 mg, 2.05 mmol) in dioxane (1 mL) and water (0.7 mL), was added KOH (346 mg, 6.17 mmol). To stirred mixture was bubbled CHIF2 gas over 30 min. Two Regioisomer products were formed with same Mass at 221 (RT=0.39 and 0.49). The reaction mixture was diluted with ether (50 mL), washed with water followed by brine solution. The organic extract was dried over sodium sulfate to give crude product which was carried onto the next step without purification. LCMS-ESI+(m/z): [M+H] Calculated for C8H11F2N3O2: 220.08; found 220.90.

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, Ethyl 3-methoxy-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gilead Sciences, Inc.; Chu, Hang; Guerrero, Juan A.; Hurtley, Anna E.; Hwang, Tae H.; Jiang, Lan; Kato, Darryl; Kobayashi, Tetsuya; Knox, John E.; Lazerwith, Scott E.; Li, Xiaofen; Lin, David W.; Medley, Jonathan W.; Mitchell, Michael L.; Naduthambi, Devan; Newby, Zachary; Squires, Neil H.; Tsui, Vickie H.; Venkataramani, Chandrasekar; Watkins, William J.; Yang, Hong; (292 pag.)US2019/352271; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 23170-45-8, name is Methyl 3-methyl-1H-pyrazole-4-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 23170-45-8, Formula: C6H8N2O2

N2 protection,Methyl-1H-pyrazole-4-carboxylate (0.14 g, 1.0 mmol), CuI (19.1 mg, 0.1 mmol), K2CO3 (0.29 g, 2.1 mmol)III1 (0.318 g, 1.2 mmol),(E) -N, N’-dimethyl-1,2-cyclohexyl diamine (28.5 mg, 0.2 mmol) and DMF (3 mL) were added to a 25 mL two-necked flask and reacted at 110 C for 24 h,Cooled to room temperature, diluted with 10 mL of water, extracted with ethyl acetate (15 mL x 3)Saturated brine (10 mL), dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure,Silica gel column (V ethyl acetate: V petroleum ether = 6: 1),0.15 g of methyl 4- (3′-cyano-4′-piperidine-phenyl) -3-methyl-pyrazole-4-carboxylate (IV1) as a yellow solid in a yield of 46.2%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-methyl-1H-pyrazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; South China University of Technology; Zhang Lei; Wu Fangping; Li Jing; Zou Yake; (15 pag.)CN106632245; (2017); A;,
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 10250-64-3 as follows. category: pyrazoles-derivatives

To a suspension of 6-(2-amino-5-chlorothiazol-4-yl)-3,4-dihydroquinolin-2(1H)-one (0.100 g, 0.41 mmol) and 1-methyl-3-phenyl-1H-pyrazole-5-carboxylic acid (0.091 g, 0.45 mmol), and pyridine (0.16 mL, 1.96 mmol) in acetonitrile (2.5 mL) in a sealed tube was added propylphosphonic anhydride solution (50 wt % in ethyl acetate, 0.61 mL, 1.02 mmol). The sealed tube was heated to 100 C. for 16 h and the precipitation formed. After cooling, the precipitate was collected by filtration and washed with cold 1:1 acetonitrile/water to give 1-methyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)-3-phenyl-1H-pyrazole-5-carboxamide (0.151 g, 86%). 1H NMR (400 MHz, DMSO-d): delta 12.94 (bs, 1H), 10.20 (s, 1H), 7.60 (m, 5H), 7.56 (s, 1H), 7.47 (m, 2H), 7.37 (m, 1H), 6.91 (d, 1H, J=8.0 Hz), 4.20 (s, 3H), 2.93 (t, 2H, J=7.2 Hz), 2.48 (partial masked under d-DMSO, m, 2H); MS (ESI): Calcd. for C23H19N5O2S: 429, found 430 (M+1)+.

According to the analysis of related databases, 10250-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nantbio, Inc.; Tao, Chunlin; Nallan, Laxman; Ho, David G.; Wang, Qinwei; Weingarten, Paul; Juncker-Jensen, Anna B.; (121 pag.)US2018/201610; (2018); 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 299930-70-4 as follows. Product Details of 299930-70-4

3-Chloro-1-methyl-4-nitro-1H-pyrazole (Stage K.2, 1 0 g 6 19 mmol) was shacked in MeOH/THF 1.1 (62 ml) under 1.1 bar H2 in presence of Raney nickel (0.35 g) as catalyst for 24 h at rt. The RM was filtered over Celite, the catalyst was washed several times with MeOH/THF and the filtrate was evaporated to dryness to give the title compound as a blue oil (HPLC tR 0.89 mm (Method A), M+H = 132 MS-ES).

According to the analysis of related databases, 299930-70-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; KALTHOFF, Frank Stephan; MAH, Robert; RAGOT, Christian; STAUFFER, Frederic; WO2010/139731; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics