Category: pyrazoles-derivatives

These common heterocyclic compound, 54384-74-6, name is 1,5-Dimethylpyrazole-3-carboxamide, 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. Application In Synthesis of 1,5-Dimethylpyrazole-3-carboxamide

To the above product (5 g, 35.97 mmol) in THF (70 mL) was added LiAlH4 (4.1 g, 107.89 mmol) in several batches at 00C. The resulting solution was refluxed for 1 hr. The solids were filtered out and the filtrate was concentrated, resulted in 3 g (67%) of 1,5- dimethyl-lH-pyrazol-3-yl)methanamine as yellow oil.

The synthetic route of 1,5-Dimethylpyrazole-3-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PONIARD PHARMACEUTICALS, INC.; WO2009/139834; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 920006-32-2,Some common heterocyclic compound, 920006-32-2, name is 1-Isopropylpyrazole-5-carboxylic Acid, molecular formula is C7H10N2O2, 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-(propan-2-yl)-1H-pyrazole-5-carboxylic acid (37.8 mg, 245 pmol), HATU (108 mg, 283 pmol), and N,N-diisopropylethylamine (99 mI, 570 mihoI), were dissolved in 3 mL of the N,N-dimethylformamide and the resulting mixture was stirred at room temperature for 15 min, then tert-butyl 3-amino-5-(3,5-dicyano-1,2,6-trimethyl-1,4-dihydropyridin-4-yl)-7-ethyl-6-fluoro-1H-indazole-1-carboxylate (100 mg, 85 % purity, 189 pmol) was added and the resulting mixture was stirred at 90 C for 16 h. The resulting mixtur e was diluted by addition of water and extracted with ethyl acetate, the combined organic phases was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by prep-HPLC (Column: XBridge Prep C18 OBD Column 19x150mm, 5 pm; Mobile Phase A: Water (10 mmol/L NH4HC03), Mobile Phase B: ACN; Flow rate: 20 mUmin; Gradient: 25% B to 65% B in 7 min; Detector: 254 nm, 220 nm) to give 39.9 mg (43% yield) of the product as a light yellow solid. LC-MS [Water(0.05%TFA)-Acetonitrile, 5%B]: Rt = 1 .38 min. MS (ESIpos): m/z = 487 (M+H)+. 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 1 .24 (t, 3H), 1 .44 (d, 6H), 2.23 (s, 6H), 2.90 (q, 2H), 3.20 (s, 3H), 4.66 (s, 1H), 5.50-5.56 (m, 1H), 7.16 (s, 1H), 7.53-7.55 (m, 1H), 7.59 (s, 1H), 10.85 (s, 1H), 13.12 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Isopropylpyrazole-5-carboxylic Acid, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; CHRIST, Clara; BRIEM, Hans; FARIA ALVARES DE LEMOS, Adelaide, Clara; BADER, Benjamin; HOLTON, Simon; BOeMER, Ulf; LIENAU, Philip; KUHNKE, Lara, Patricia; (122 pag.)WO2019/185525; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 754219-01-7, name is Ethyl 5-iodo-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C7H9IN2O2, 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. category: pyrazoles-derivatives

A mixture of ethyl 5-iodo-1-methyl-pyrazole-4-carboxylate (7.5 g, 26.8 mmol) and lithium hydroxide (6.4 g, 268.0 mmol) in tetrahydrofuran (100 mL) and water (100 mL) was stirred at 25 C. for 15 h and concentrated under reduced pressure. The residue was adjusted to pH=5 by additional of hydrochloric acid (2 N). The formed solid was collected by filtration, washed with water (20 mL) and dried in vacuo to afford crude 5-iodo-1-methyl-1H-pyrazole-4-carboxylic acid (6.0 g, 89%) as a white solid, used as is in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 754219-01-7, its application will become more common.

Reference:
Patent; Genentech, Inc.; Patel, Snahel; Hamilton, Gregory; (73 pag.)US2018/170927; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 150712-24-6, 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. 150712-24-6, name is 5-Benzyl-1H-pyrazol-3-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of 0.02 g of 5-benzyl-2H-pyrazol-3-ylamine and 0.03 g of 4-(2,3-difluoro- phenylsulfanyl)-3-oxo-butyric acid methylester(lntermediate A) in 1 ml of AcOH is heated at 70 C for 4 hours. On cooling, the mixture obtained is diluted with 10 ml of EtOAc, washed with H2O, brine and dried. The residue obtained is filtered and solvent is evaporated. The product obtained is stirred with Et2O at RT for 16 hours. The precipitate obtained is filtered off and dried. The title compound is obtained. [M+H]+: 384.

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-Benzyl-1H-pyrazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; WO2008/62026; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 1269293-48-2, name is Ethyl 5-bromo-1-methyl-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1269293-48-2

STEP A: 5-Bromo-1-methyl-1H-pyrazole-3-carboxylic acid [0180] Lithium hydroxide (8.58 mL, 17.16 mmol) was added to a mixture of ethyl 5- bromo-1 -methyl- lH-pyrazole-3-carboxylate (1 g, 4.29 mmol) in THF (10 mL) and water (2 mL). The reaction mixture was stirred for 5 hours at room temperature and was subsequently concentrated, acidified with concentrated HC1, and extracted into EtOAc. The organic layer was dried over Na2S04 and concentrated to give the title compound as a white solid (0.72 g, 82%).

The synthetic route of 1269293-48-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHERUVALLATH, Zacharia; KOMANDLA, Mallareddy; LAWSON, John David; MCBRIDE, Christopher; TANG, Mingnam; WO2014/39831; (2014); 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. 139756-04-0, name is 1-Methyl-4-(2-propoxybenzamido)-3-propyl-1H-pyrazole-5-carboxamide, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C18H24N4O3

Step 9 3-(5-Carbamoyl-1-methyl-3-propyl-1H-pyrazol-4-ylcarbamoyl)-4-propxy-benzenesulfonyl chloride: 2-Methyl-4-(2-propoxybenzoylamino)-5-propyl-2H-pyrazole-3-carboxamide (20 g, 58.1 mmol) was added to chlorosulfonic acid (81.3 g, 698 mmol) at 0 C. and the reaction was warmed to ambient temperature and stirred for 2 hours. The reaction mixture was poured into ice water (800 g) and mechanically stirred for 1 hour to give a white solid, which was filtered and washed with water. Following standard extractive work up, the solvent was evaporated under reduced pressure to yield the title compound (8 g, 31%). 1H NMR (300 MHz, CDCl3) delta 9.19 (s, 1H), 8.97 (s, 1H), 8.19 (t, 1H, J=8.9 Hz), 7.56 (br. s, 1H), 4.35 (t, 2H, J=6.6 Hz), 4.07 (s, 3H), 2.53 (t, 2H, J=7.5 Hz), 2.06-1.94 (m, 2H), 1.78-1.60 (m, 2H), 1.18 (t, 3H, J=7.5 Hz), 0.95 (t, 3H, J=7.2 Hz); LC-MS: m/z=443.1 (M+H)+

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 139756-04-0.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; US2008/194529; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 143426-49-7, name is (4-Pyrazol-1-yl-phenyl)methanol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H10N2O

To a solution of l-(4-hydroxymethylphenyl)-lH-pyrazole (1.0 g, 0.005 mole) in DCM (25 mL) at 0 C under N2, was added phosphorus tribromide (0.64 mL, 0.0068 mole) drop wise. Reaction mixture was warmed to RT and stirred for 2 h. The reaction mixture was diluted with DCM (75 mL), treated with saturated aqueous sodium bicarbonate (20 mL). Organic layer was washed with water (30 mL), brine solution (30 mL) and dried over Na2S04 and concentrated under vacuum to obtain the title compound. (0227) Yield: 1.25 g; 1H – NMR (DMSO -d6, 400 MHz) d ppm: 4.76 (s, 2H), 6.55 (s, 1H), 7.56 – 7.58 (d, J = 8.5 Hz, 2H), 7.75 (s, 1H), 7.82 – 7.84 (d, J = 8.4 Hz, 2H), 8.51 – 8.52 (d, J = 2.4 Hz, 1H); Mass (m/z): 236.9 (M+H)+, 239 (M+H)+.

The synthetic route of 143426-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; SHINDE, Anil Karbhari; MOHAMMED, Abdul Rasheed; BADANGE, Rajesh Kumar; PALACHARLA, Raghava Choudary; JASTI, Venkateswarlu; (61 pag.)WO2019/102365; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 59074-26-9,Some common heterocyclic compound, 59074-26-9, name is 3-(4-Chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole, molecular formula is C15H13ClN2, 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.

Part A: A stirred solution of 3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (5.00 gram, 19.5 mmol) and N-(tert-butoxycarbonyl)aziridine (2.00 gram, 14.0 mmol) in toluene (100 ml) was heated at reflux temperature for 16 hours. After concentration in vacuo the residue was purified by flash chromatography (petroleum ether/diethyl ether=3/1 (v/v)), followed by petroleum ether/diethyl ether=1/1 (v/v)). After concentration in vacuo the remaining oily residue was crystallized from diisopropyl ether to afford 1-[2-((tert-butoxycarbonyl)amino)ethyl]-3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (1.91 gram, 34%). Repeated crystallisations from the mother liquor afforded an additional amount of crystalline 1-[2-((tert-butoxycarbonyl)amino)ethyl]-3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole (1.19 gram).

The synthetic route of 59074-26-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Solvay Pharmaceuticals B.V.; US2001/53788; (2001); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 25700-12-3,Some common heterocyclic compound, 25700-12-3, name is 3-(1H-Pyrazol-1-yl)pyridine, molecular formula is C8H7N3, 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 2: Preparation of 3-(4-nitro-pyrazol-1-yl)-pyridine 3-Pyrazol-1-yl-pyridine (2 g, 0.032 mol) was dissolved in concentrated H2SO4 (32 mL 0.598 mmol) and cooled at -5 C. using an ice bath. To the reaction mass, a 1:1 mixture of concentrated HNO3 (30 mL, 0.673 mmol) and concentrated H2SO4 (30 ml, 15 Vol.) was added dropwise over a period of 30 min. Cooling was discontinued and the reaction mixture was stirred at room temperature overnight. After the reaction was complete, the mixture was poured over crushed ice and neutralized with saturated NaHCO3, filtered, washed with water and dried to furnish the nitro pyrazole as pale yellow solid (1.8 g, 68%): 1H NMR (400 MHz, DMSO-d6) delta 9.03 (d, J=2.8 Hz, 1H); 8.70 (dd, J=4.8, 1.6 Hz, 1H), 8.69 (s, 1H), 8.33 (s, 1H), 8.11-8.08 (m, 1H), 7.51 (dd, J=8.4, 4.8 Hz, 1H); MS (m/z) 191 [M+1].

The synthetic route of 25700-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; Buysse, Ann M.; Niyaz, Noormohamed M.; Demeter, David A.; Zhang, Yu; Walsh, Martin J.; Kubota, Asako; Hunter, Ricky; Trullinger, Tony K.; Lowe, Christian T.; Knueppel, Daniel; Patny, Akshay; Garizi, Negar; LePlae, JR., Paul Renee; Wessels, Frank; Ross, JR., Ronald; DeAmicis, Carl; Borromeo, Peter; US2013/288893; (2013); 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 25700-12-3 as follows. Safety of 3-(1H-Pyrazol-1-yl)pyridine

3-Pyrazol-1-yl-pyridine (2 g, 0.032 mol) was dissolved in concentrated H2SO4 (32 mL 0.598 mmol.) and cooled to -5 C. using an ice bath. To the reaction mass, a 1:1 mixture of concentrated HNO3 (30 mL, 0.673 mmol) and concentrated H2SO4 (30 ml, 15 Vol.) was added dropwise over a period of 30 min Cooling was discontinued and the reaction mixture was stirred at room temperature overnight. After the reaction was complete, the mixture was poured over crushed ice and neutralized with saturated NaHCO3, filtered, washed with water and dried to furnish the nitro pyrazole as pale yellow solid (1.8 g, 68%): 1H NMR (400 MHz, DMSO-d6) delta 9.03 (d, J=2.8 Hz, 1H); 8.70 (dd, J=4.8, 1.6 Hz, 1H), 8.69 (s, 1H), 8.33 (s, 1H), 8.11-8.08 (m, 1H), 7.51 (dd, J=8.4, 4.8 Hz, 1H); MS (m/z) 191 [M+1].

According to the analysis of related databases, 25700-12-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow Agrosciences LLC; Niyaz, Noormohamed M.; Garizi, Negar; Zhang, Yu; Trullinger, Tony K.; Hunter, Ricky; Buysse, Ann M.; Kubota, Asako; LePlae, Jr., Paul Renee; Knueppel, Daniel; Lowe, Christian T.; Pernich, Dan; Demeter, David A.; Johnson, Timothy C.; US2013/109566; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics