Tag: M.W:100-200

Synthetic Route of 138786-86-4,Some common heterocyclic compound, 138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate, molecular formula is C5H5N3O4, 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 4-nitro-lH-pyrazole-3-carboxylic acid methyl ester (3.1 g, 18.1 mmol) in dry acetone (2 ml) was added K2C03 (5 g, 36.2 mmol) at 25C. The reaction mixture was cooled to 0C, and methyl iodide (2.2 ml, 36.3 mmol) was added. The temperature was again raised to 25C, and then heated to 70C for 2 hrs. The solvent was removed in vacuo The residue was diluted with EtOA and washed with water and with brine, dried (Na2S04), filtered, and concentrated. The crude product was purified by column chromatography over silica gel. Elution with 20% EtOAc/hexane) gave the undesired isomer 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid methyl ester (1 g, 30%), subsequent elution with 40% EtOAc/hexane provided the desired isomer l-methyl-4-nitro-lH-pyrazole-3-carboxylic acid methyl ester (1.8 g, 54%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-nitro-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLEICHER, Konrad; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; GRUBER, Felix; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RODRIGUEZ SARMIENTO, Rosa Maria; WO2011/154327; (2011); A1;,
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These common heterocyclic compound, 100114-57-6, name is 3-Cyclopropyl-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. Computed Properties of C6H8N2

To a solution of 6-chloronicotinonitrile (100 mg, 0.74 mmol) in DMF (2 mL), was added 3-cyclopropyl-1H-pyrazole (80 mg, 0.74 mmol), and Cs2CO3 (470 mg, 1.48 mmol). The mixture was stirred at 90C for 5 hours. To the mixture was added water and extracted with ethyl acetate. The organic layer was dried with anhydrous Na2SO4, and concentrated under vacuo to give 120 mg of 6-(3-cyclopropyl-1H-pyrazol-1-yl)nicotinonitrile as a light yellow solid. The structure was confirmed by LC-MS.

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

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; FLEMING, Paul, E.; (62 pag.)WO2016/127074; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 31037-02-2, 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. 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Ethyl 4-hydroxy-l-methyl-6-oxo-6,7-dihydro-lH-pyrazolo[3,4- delta]pyridine-5-carboxylate 3O ONaOEt / EtOH Reflux [00192] Sodium ethoxide (95%, 83g, 1.18 moles) was dissolved in 175 mL of absolute ethanol, following the protocol described in J. Heterocyclic Chem. (1978) 15:319 with some modifications. Diethylmalonate 2 (184.6 g, 1.18 moles) was added and stirred at room temperature for 10 minutes. Ethyl 5-amino-l-methylpyrazole-4-carboxylate 1 (5Og, 0.295 moles) was added slowly and the resulting solution refluxed overnight at 100 0C. During the reflux period, an off-white solid began to form. The solution was evaporated to dryness on a rotary evaporator and the residue dissolved in a minimum amount of water. Upon acidification (pH 2) of the aqueous solution with concentrated hydrochloric acid, the resulting precipitate was filtered and recrystallized from acetic acid-water to give 3 as a white solid (~45g , 64%). NMR (trifluoroacetic acid): delta 1.60(t.3H.J=7Hz, CH3 of ester), 4.22(s, 3H, N- CH3), 4.80 (q, 2H, j=7hz, CH2), 8.49 (s, IH, H-3)

The synthetic route of Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; DOTSON, Jennafer; HEFFRON, Tim; OLIVERO, Alan G.; SUTHERLIN, Daniel P.; STABEN, Steven; WANG, Shumei; ZHU, Bing-Yan; CHUCKOWREE, Irina S.; FOLKES, Adrian J.; WAN, Nan Chi; WO2010/59788; (2010); A1;,
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Related Products of 55864-87-4,Some common heterocyclic compound, 55864-87-4, name is Ethyl 4-nitro-1H-pyrazole-3-carboxylate, molecular formula is C6H7N3O4, 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 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester (6.40 g, 34.6 mmol) and 10% Pd/C (650 mg) in EtOH (150ml) was stirred under an atmosphere of hydrogen for 20 h. The mixture was filtered through a plug of Celite, reduced in vacuo and dried through azeotrope with toluene to afford 4-amino-1H-pyrazole-3- carboxylic acid ethyl ester as a pink solid (5.28 g, 98%). (1H NMR (400 MHz, DMSO-d6) delta 12. 7 (s, 1H), 7.1 (s, 1H), 4. 8 (s, 2H), 4.3 (q, 2H), 1.3 (t, 3H)).

The synthetic route of 55864-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX TECHNOLOGY LIMITED; WO2005/12256; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C6H8N2O

In a sealed tube, under N2, 1,3-dimethyl-1H-pyrazole-4-carbaldehyde (284 mg; 2.28mmol) and Ti(iPrO)4 (727 jiL; 3.05 mmol) were added to a solution of intermediate 11(500 mg; 1.52 mmol) in THF (10 mL). The solution was stirred at 50C for 2h. Thereaction mixture was cooled to 5C and iPrMgCl (3.8 mL; 7.61 mmol) was addeddropwise. The reaction mixture was allowed to rise slowly to rt and stirred overnight. The reaction mixture was poured onto a 10% aqueous solution of K2C03 and EtOAc. The insoluble was filtered through a pad of celite then, the organic layer was decanted, dried over MgSO4, filtered and the solvent was evaporated. The residue (866 mg, brownoil) was purified by chromatography over silica gel (Si02 40 g; eluent: from 96% DCM,4% MeOH, 0.4% NH4OH to 93% DCM, 7% MeOH, 0.7% NH4OH). The pure fractionswere collected and the solvent was evaporated to dryness. The residue (496 mg, yellow oil) was recrystallized with diethylether. The precipitate was filtered and dried to give324 mg of compound 161( (45%, white solid).

The synthetic route of 25016-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PILATTE, Isabelle, Noelle, Constance; PATRICK, Aaron, Nathaniel; (250 pag.)WO2018/50686; (2018); A1;,
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42027-81-6, name is 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, 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 42027-81-6

To a stirred solution of 2-(4-nitro-1H-pyrazol-1-yl)ethanol 17 (2.0 g, 1.23 mmol) in EtOH (25 mL), 0.40 g of Pd(OH)2 added and then stirred reaction under H2 gas atm for 1 4h. After the completion of reaction (TLC monitoring) the reaction mixture was filtered through celite bed, washed with MeOH, concentrated the solvent and the crude compound was purified by triturating with ether and pentane to give 2-(4-amino-1H- pyrazol-1-yl)ethanol precursor-07 as brown solid (1.30 g, 81% yield). MS: 128.07 (M+H).

The synthetic route of 42027-81-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; KETHIRI, Raghava Reddy; VISWANADHAN, Vellarkad Narayana; GIRI, Sanjeev; WO2015/25197; (2015); A1;,
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Synthetic Route of 25016-20-0, 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. 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

Example 67;(i?)-(l-Methyl-l/-r-pyrazoI-3-yl)(l-(4-(trifluoromethyl)phenyl)-3,4-dihydroiso- quinoIin-2(lH)-yl)methanone; A solution of (R)- -(4-(trifluoromethyl)phenyl)- 1,2,3, 4-tetrahydroisoquinoline (58 mg, 0.21 mmol, example 30, step 1) in DMF (1 mL) was added 1-methyl-leta- pyrazole-3-carboxylic acid (Fluorochem, 34 mg, 0.27 mmol), 1-hydroxybenzo- triazole hydrate (42 mg, 0.27 mmol), and JV-((isopropylimino)methylene)propan- 2-amine (66 muL, 0.42 mmol). The resulting mixture was then stirred at RT for 16 h. Then, the mixture was filtered and the filtrate was purified by preparative HPLC to give the target compound. The product was dissolved in MeOH and passed through PL-HCO3 MP resin and the resin was washed with MeOH (2 x 0.3 mL). The combined filtrates were concentrated and dried under vacuum to give the title compound as a light-yellow solid. MS (ESI, positive ion) m/z: 386 (M+H).

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-pyrazole-3-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; WO2009/73203; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 113100-53-1,Some common heterocyclic compound, 113100-53-1, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-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.

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-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (0.087 g, 0.45 mmol), and pyridine (0.15 mL, 1.83 mmol in acetonitrile (5 mL) in a sealed tube was added propylphosphonic anhydride solution (50 wt % in ethyl acetate, 0.60 mL, 1.02 mmol). The sealed tube was heated to 100 C. for over night 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-(trifluoromethyl)-1H-pyrazole-4-carboxamide (0.120 g, 70%). 1H NMR (400 MHz, DMSO-d): delta 12.61 (bs, 1H), 10.19 (s, 1H), 8.76 (s, 1H), 7.74 (m, 1H), 7.69 (dd, 1H, J=8.4, 2.0 Hz), 7.50 (s, 1H), 6.90 (d, 1H, J=8.0 Hz), 4.00 (s, 3H), 2.92 (t, 2H, J=7.2 Hz), 2.48 (partial masked under d-DMSO, m, 2H); MS (ESI): Calcd. For C18H14F3N5O2S: 421, found 422 (M+1)+.

The synthetic route of 113100-53-1 has been constantly updated, and we look forward to future research findings.

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

4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, 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. category: pyrazoles-derivatives

General procedure: A mixture of substituted 3-(2-aryl-2-oxoethylidene)indolin-2-one 1 (1 mmol), 1,3-dimethylurea (2, 1.2 mmol) or 5-amino-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (4, 1 mmol), PTSA·H2O (0.3 mmol), and MeCN (5 mL) was added to a 25 mL flask and reacted at 80 C (monitored by TLC) about 2 h. After completion, the mixture was cooled to r.t. and the precipitate obtained was isolated by filtration and drying. Compounds 3 or 5 were purified by recrystallization (DMF or EtOH).

The synthetic route of 4149-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dai, Lei; Shu, Ping; Wang, Zhansheng; Li, Qingyang; Yu, Qiuyu; Shi, Yanhui; Rong, Liangce; Synthesis; vol. 49; 3; (2017); p. 637 – 646;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 18213-75-7, A common heterocyclic compound, 18213-75-7, name is 5-Amino-1-methyl-1H-pyrazole-4-carboxamide, molecular formula is C5H8N4O, 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.

Isopropyl chloroformate (1.95 g, 14.3 mmol) and N-methylmorpholine (1.44 g, 14.3 mmol) were added to a solution of 4,4,4-trifluorobutanoic acid (2.03 g, 14.3 mmol) in THF (40 mL) at -15C. The solution was stirred for 10 min then cooled to -50C and a solution of 5-amino-1-methyl-1H-pyrazole-4-carboxamide (2.0 g, 14.3 mmol) and DIEA (2.49 ml, 14.3 mmol) in DMF (20 ml) was added. The solution was allowed to slowly warm to ambient temperature over 2 h. The solution was diluted with EtOAc and washed with brine. The organic layer was dried, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography using 0% to 15% MeOH in CH2CI2 gradient to give the title compound.

The synthetic route of 18213-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAN, Xiaoqing; WHITEHEAD, Alan; RAGHAVAN, Subharekha; CERNAK, Timothy, A.; DREHER, Spencer; GROEPER, Jonathan; GUO, Jian; ZHANG, Yong; WO2015/88886; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics