Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 75092-30-7, name is 4-Iodo-1-methyl-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 75092-30-7, Safety of 4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid

A round-bottom flash was charged with 4-iodo-i -methyl-i H-pyrazole-5-carboxylic acid(297 g, i.i8 mol), DCM (2.97 L), and i,i?-carbonyldiimidazole (CDI) (207 g, 97% bymass, 1.24 mol). The reaction mixture was stirred at room temperature for 45 mm.Ammonium chloride (189 g, 3.53 mol) and triethylamine (498 mL, 3.53 mol) were addedand the reaction mixture was stirred at room temperature overnight. The reaction mixturewas concentrated in vacuo and the residue was suspended in H20 (-3 L) and granulated at room temperature for 1 h. The solid was collected via filtration, washed with H20, and dried in a vacuum oven to afford 4-iodo-i -methyl-i H-pyrazole-5-carboxamide as a colorless solid (222 g, 75% yield).1H NMR (CDCI3) O: 7.53 (5, 1 H), 6.56 (br s, 1 H), 6.01 (br s, 1 H), 4.21 (5, 3H). UPLC (UPLC-MS Method 1): tR = 0.15 mm.MS (ES+): 251.1 (M+H).

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

Reference:
Patent; PFIZER INC.; DAROUT, Etzer; MCCLURE, Kim F.; PIOTROWSKI, David; RAYMER, Brian; (120 pag.)WO2016/55901; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 13599-12-7, 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. 13599-12-7, name is Ethyl 3-phenyl-1H-pyrazole-5-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Ethyl-1-(2-(tert-butoxycarbonylamino)ethyl)-3-phenyl-1H-pyrazole-5-carboxylate A mixture of ethyl 3-phenyl-1H-pyrazole-5-carboxylate (2.16 g, 10 mmol), tert-butyl-2-hydroxyethylcarbamate (3.22 g, 20 mmol), DIAD (4.04 g, 20 mmol), and PPh3 (5.24 g, 20 mmol) in THF (70 mL) was stirred at rt for 16 hrs. The mixture was then concentrated and purified by chromatography (silica, EtOAc/PE=1/7) to afford ethyl 1-(2-(tert-butoxycarbonylamino)ethyl)-3-phenyl-1H-pyrazole-5-carboxylate (2.3 g, 6.4 mmol, 64%). ESI-MS (EI+, m/z): 360.3 [M+H]+.

The synthetic route of Ethyl 3-phenyl-1H-pyrazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (136 pag.)US2019/389843; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 330792-70-6, name is 3-Amino-5-(4-phenoxyphenyl)pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C16H12N4O

3-Amino-4-cyano-5-(4-phenoxyphenyl)pyrazole (100g) was suspended in formamide (500ml) and heated at a temperature of 135-140°C, after completion of reaction, the reaction mixture was cooled to a temperature of 30-35°C and demineralized water (1000ml) was added and the reaction mixture was stirred at a temperature of 20-25°C for 1 hour. The resulting solid was filtered, washed with water (500ml) then successively slurry washed with toluene (2 x 500ml) and dried to afford pure 4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine compound of formula I (70g) having purity 99.8percent measured by HPLC; assay > 98percent; residue on ignition 0.05percent; heavy metals <20ppm. According to the analysis of related databases, 330792-70-6, the application of this compound in the production field has become more and more popular. Reference:
Patent; IND-SWIFT LABORATORIES LIMITED; ARUL, Ramakrishnan; SARIN, Gurdeep Singh; WAS, Sandeep; KUMAR, Vishal; (26 pag.)WO2017/163257; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 345637-71-0, 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. 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-(5-methyl-3-(trifluoromethyl)-l H-pyrazol- l -yl)acetic acid ( 129 mg, 0.6 mmol) in N, N-dimethyformamide ( 5 mL), l -[bis(dimethylamino)methylene]- l H-l ,2,3-triazolo[4,5-b]pyridinium 3- oxid hexafluorophosphate (HATU) (258 mg, 0.7 mmol) and N, N-diisopropylethylamine (0.6 mL, 3.4 mmol) was added. The resulting clear solution was stirred for 10 min at 25 C. N-((2,6- difluorophenyl)(methyl)(o o)-lambda6-sulfanylidene)-2-(piperidin-4-yl)thiazole-4-cai·boxamide (21 8 mg, 0.6 mmol) was added and the resulting yellow solution was stirred for 16 h at 25 C. After completion of the reaction, the reaction mixture was quenched with a brine solution ( 1 50 mL). The reaction mixture was extracted twice with ethyl acetate (50 mL). The ethyl acetate layer was concentrated and the residue was purified using column chromatography using 80% ethyl acetate in hexane as an eluent to obtain N-((2,6- difluorophenyl)(methyl)(oxo)-6-sulfanylidene)-2-( l -(2-(5-methyl-3-(trifluoromethyl)- l H^yl)acetyl)piperidin-4-yl)thiazole-4-carboxamide (26 mg, 0.05 mmol, 8% yield).-NMR (400 MHz, DMSO-d6) delta 8.28 (s, 1 H), 7.80-7.87 (m, 1 H), 7.38 (t, J = 9.0 Hz, 2H), 7.1 8 (t, J = 53.3 Hz, 1 H), 7.04 (t, J = 54.2 Hz, 1 H), 6.92-7.22 (m, 1 H), 5.40 (dd, J = 33.2, 16.6 Hz, 2H), 4.35 (d, J = 13.0 Hz, 1 H), 3.97 (d, J = 13.0 Hz, 1 H), 3.72 (s, 3H), 3.25 (t, J = 1 1 .9 Hz, 1 H), 2.79-2.85 (m, 1 H), 2.08 (s,3H), 1 .78 (dd, J = 28.0, 1 5.0 Hz, 1 H), 1 .50- 1 .59 (m, 1 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, 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PI INDUSTRIES LTD.; SHANBHAG, Gajanan; SHARMA, Aditya; RENUGADEVI, G.; PABBA, Jagadish; DENGALE, Rohit Arvind; ROY, Dipankar; S.P., Mohan Kumar; BELKAR, Yogesh Kashiram; AUTKAR, Santosh Shridhar; GARG, Ruchi; VENKATESHA, Hagalavadi M; KLAUSENER, Alexander Guenther Maria; (114 pag.)WO2019/48988; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1029413-51-1,Some common heterocyclic compound, 1029413-51-1, name is 4-Amino-1-(1-boc-azetidin-3-yl)-1H-pyrazole, molecular formula is C11H18N4O2, 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.

[0483j To a solution of N-(2-(2-chloropyrimidin-4-yl)-6,7,8 ,9-tetrahydro-5H- benzo [7] annulen-5 -yl)-3 -isopropoxyazetidine- 1 -carboxamide (130 mg, 0.32 mmol) in 1,4- dioxane (5 mL) were added 1-ethyl-1H-pyrazol-4-amine (36 mg, 0.32 mmol), Pd2(dba)3 (29 mg, 0.032 mmol), S-Phos (26 mg, 0.064 mmol) and Cs2CO3 (312 mg, 0.96 mmol). The mixture was stirred at 100 C for 2 h. After diluted with water (50 mL), the mixture was extracted with EtOAc (60 mL x 2). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by prep-HPLC (CH3CN/H20 with 0.05% NH4OH as mobile phase) to give N-(2-(2-(( 1-ethyl-i H-pyrazol-4-yl)amino)pyrimidin-4-yl)-6,7,8 ,9-tetrahydro-5H- benzo[7]annulen-5-yl)-3-isopropoxyazetidine-1-carboxamide as a yellow solid (129 mg, yield:73%). [0574j Synthesis of tert-butyl 3 -(4-((4-(4-((3 -(tert-butoxy)azetidine- 1- carboxamido)methyl)-3 -(trifluoromethyl)phenyl)pyrimidin-2-yl)amino)- 1H-pyrazol- 1- yl)azetidine-1-carboxylate was similar to that of Example 161. The residue was purified by silica gel chromatography column (EtOAc: petroleum ether = 10:1) to give tert-butyl 3-(4-((4-(4- ((3 -(tert-butoxy)azetidine- 1 -carboxamido)methyl)-3 -(trifluoromethyl)phenyl)pyrimidin-2- yl)amino)-1H-pyrazol-1-yl)azetidine-1-carboxylate as a yellow solid (230 mg, yield: 46%). ESIMS (M+H) : 645.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-1-(1-boc-azetidin-3-yl)-1H-pyrazole, its application will become more common.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 15115-52-3, These common heterocyclic compound, 15115-52-3, name is 4-Bromo-1-phenyl-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.

Intermediate I-1 (15 mg, 0.045 mmol) and 4-bromo-1-phenyl-1H-pyrazole (14.93 mg, 0.067 mmol) were dissolved in DMF (446 muL). PdCl2(dppf)-CH2Cl2 (2.187 mg, 2.68 mumol) was added and the reaction mixture was degassed by bubbling with argon for 15 minutes. Sodium carbonate (2 M, 26.8 muL, 0.054 mmol) was added and the reaction mixture was degassed for 5 minutes, then sealed and heated to 90 C in the microwave for 30 minutes. The reaction mixture was diluted with DMF, filtered, and purified by preparative HPLC (Method D, 40 to 75% B in 20 minutes) to give Example 2 (3.0 mg, 0.00823 mmol, 18.4%): 1H NMR (500MHz, METHANOL-d4) delta 8.89 (s, 1H), 8.61 (s, 1H), 8.34 (s, 1H), 7.86-7.75 (m, 3H), 7.70-7.56 (m, 2H), 7.55-7.48 (m, 2H), 7.40-7.33 (m, 1H), 2.62 (s, 3H); LC-MS: Method H, RT = 1.18 min, MS (ESI) m/z: 352.9 (M+H)+ Analytical HPLC Method B: 96.6% purity.

The synthetic route of 15115-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; RICHTER, Jeremy M.; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; (111 pag.)WO2018/13772; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 398495-65-3,Some common heterocyclic compound, 398495-65-3, name is 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate, molecular formula is C13H20N4O4, 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.

A solution of 3-amino-5-tert-butyloxycarbonyl-1-ethoxycarbonyl- -4, 6- dihydropyrrolo [3,4-c] pyrazole (0.4g, 1.35 mmol) in dry tetrahydrofurane [(10ML)] was added drop wise to a solution of isoamylnitrite (0. [32ML,] 2. [36MMOL)] in dry tetrahydrofurane (2ml) maintained at reflux. The resulting solution was stirred at reflux for 4 hours, and then cooled to room temperature. After removal of the solvent under vacuum, the crude material was purified by flash chromatography on silica gel using n- [HEXANE. ETHYL] acetate [90No.10 ]; 70-30. The title compound was obtained as a light yellow oil (200mg, y 53%). [H-NMR] (DMSO-d6) [8] ppm: 7.67 (s, 1H); 4.54 (m, 2H); 4.39 (q, 2H); 4.32 (m, [2H)] ; 1.43 (s, 9H); 1.31 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate, its application will become more common.

Reference:
Patent; PHARMACIA ITALIA SPA; WO2004/13144; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1264097-17-7, 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 1264097-17-7 as follows.

A mixture of l-benzyl-lH-pyrazol-4-amine hydrochloride (510 mg, 2.43 mmol, 1.19 equiv), 2,6-dichloro-9-(2-methylpropyl)-9H-purine (500 mg, 2.04 mmol, 1.00 equiv), i-propanol (5 mL) and DIEA (1.05 g, 8.12 mmol, 3.98 equiv) was stirred for 6 h at 100C in an oil bath. The resulting mixture was concentrated under vacuum to remove the solvents. The residue was purified on a silica gel column with dichloromethane/methanol (100/1) to afford 600 mg (crude) of N-(l-benzyl-lH-pyrazol-4-yl)-2-chloro-9-(2-methylpropyl)-9H-purin-6-amine as a dark red solid.

According to the analysis of related databases, 1264097-17-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BURCH, Jason; ORTWINE, Daniel; PEI, Zhonghua; (118 pag.)WO2016/91916; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 129768-30-5,Some common heterocyclic compound, 129768-30-5, name is Ethyl 3-(Trifluoromethyl)pyrazole-5-carboxylate, molecular formula is C7H7F3N2O2, 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 ethyl 3-(trifluoromethyl)-lH-pyrazole-5-carboxylate (2 g, 9.615 mmol, 1 eq) in THF (30 ml) was added LiAlH4 (1.09g, 28.846 mmol, 3 eq), portionwise at 0C for 10 min. The RM was stirred at RT for 2h.The RM was quenched with sat Na2S04 (50 ml) and most of the solvent was removed under reduced pressure. The residue was diluted with water (100 ml) and extracted with EtOAc (3x 100 ml). The combined organic layers were washed with brine (100ml), dried(Na2S04) and concentrated to afford the title compound (1.5 g, 94%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-(Trifluoromethyl)pyrazole-5-carboxylate, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stephan; REICH, Melanie; KOENIGS, Rene, Michael; (72 pag.)WO2017/59966; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1105039-93-7, These common heterocyclic compound, 1105039-93-7, name is 1-(4-Methoxybenzyl)-1H-pyrazole-4-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.

A mixture of 1-(4-methoxy-benzyl)-1H-pyrazole-4-carboxylic acid (0.45 g, 1.94 mmol), oxalyl chloride (1.2 ml) and DMF (1 drop) was heated at 60 C. for 1 h. The mixture was allowed to cool to ambient temperature and evaporated to afford the title compound as a colourless oil (0.48 g, 99%). The material was used in the next step without further purification.

Statistics shows that 1-(4-Methoxybenzyl)-1H-pyrazole-4-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 1105039-93-7.

Reference:
Patent; Genentech, Inc.; Dyke, Hazel Joan; Gancia, Emanuela; Gazzard, Lewis J.; Goodacre, Simon Charles; Lyssikatos, Joseph P.; MacLeod, Calum; Williams, Karen; Chen, Huifen; US2015/368244; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics