Category: 175277-11-9

Application of 175277-11-9,Some common heterocyclic compound, 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, molecular formula is C9H14N2O2, 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.

46) 3-(tert-butyl)-N-(6-fluoro-2,3-dimethoxybenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (250 mg, 1.36 mmol, 1.0 eq) in toluene (15 mL) was added 2,4-dimethoxybenzyl amine (227 mg, 1.36 mmol, 1.0 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (15 mL) and then NaBH4 (103 mg, 2.72 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in Ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (0.45 mmol, 1.1 eq) in DMF (5 mL) were added the acid (75 mg, 0.407 mmol, 1.0 eq), DIEA (262 mg, 2.04 mmol, 5 eq) and HBTU (205 mg, 0.54 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (20 mL) and washed with 10% aq HCl (1*20 mL), sat NaHCO3 (1*20 mL) and water (4*20 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25% to 75%)) to give the amide, which was directly used in the next step. The amide was treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product. Mass Spectrum (LCMS, ESI Pos.) Calcd. For C18H25FN3O3: 350.0 (M+H), Found 350.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, its application will become more common.

Reference:
Patent; Prosetta Antiviral ,Inc.; Selvarajah, Suganya; Paulvannan, Kumar; (58 pag.)US2018/118679; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 175277-11-9, 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. 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of 6-(2-amino-5-chlorothiazol-4-yl)-3,4-dihydroquinolin-2(1H)-one (0.200 g, 0.82 mmol) and 3-(tert-butyl)-1-methyl-1H-pyrazole-5-carboxylic acid (0.164 g, 0.96 mmol), and pyridine (0.32 mL, 4 mmol) in acetonitrile (5 mL) in a sealed tube was added propylphosphonic anhydride solution (50 wt % in ethyl acetate, 0.13 m L, 2.04 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 3-(tert-butyl)-1-methyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)-1H-pyrazole-5-carboxamide (0.216 g, 65%). 1H NMR (400 MHz, DMSO-d): delta 12.60 (bs, 1H), 10.19 (s, 1H), 7.75 (m, 1H), 7.71 (dd, 1H, J=8.4, 2.0 Hz), 7.53 (s, 1H), 7.33 (s, 1H), 6.91 (d, 1H, J=8.0 Hz), 4.09 (s, 3H), 2.94 (t, 2H, J=7.2 Hz), 2.48 (partial masked under d-DMSO, m, 2H), 1.27 (s, 9H). MS (ESI): Calcd. for C21H23N5O2S: 409, found 410 (M+1)+.

The synthetic route of 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid 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

175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, 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. HPLC of Formula: C9H14N2O2

3-tert-butyl-1-methyl-1H-pyrazole-5-carboxylic acid (0.090 g, 0.49 mmol) was dissolved in CH2Cl2 (5 mL). DMAP(0.005 g, 0.04 mmol) and EDC (0.163 g, 0.85 mmol) were added, and the mixture was stirred for15 min at room temperature. The TFA salt was suspended in CH2Cl2 (3 mL) and treated withtriethylamine (136 muL, 0.98 mmol) at 0C. The resulting mixture was dropwise combined withthe activated acid and stirred for 18 h at room temperature. The solvent was evaporated under reduced pressure. The residue was treated with H2O and extracted with ethyl acetate (3 × 10 mL).The combined organic layers were washed with sat. NaHCO3 (3 × 10 mL), H2O (20 mL), andbrine (20 mL). The solvent was dried over MgSO4 and removed under reduced pressure. Thecrude residue was purified by silica column chromatography using EtOAc as eluent to obtain C(33 % yield).

The synthetic route of 175277-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Silva, Daniel G.; Ribeiro, Jean F.R.; De Vita, Daniela; Cianni, Lorenzo; Franco, Caio Haddad; Freitas-Junior, Lucio H.; Moraes, Carolina Borsoi; Rocha, Josmar R.; Burtoloso, Antonio C.B.; Kenny, Peter W.; Leitao, Andrei; Montanari, Carlos A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5031 – 5035;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-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 175277-11-9, name: 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid

27) 3-(tert-butyl)-N-(3-methoxy-4-methylbenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of 3-Methoxy-3-methyl-benzaldehyde (250 mg, 1.66 mmol, 1.0 eq) in toluene (20 mL) was added 2,4-dimethoxybenzyl amine (306 mg, 1.83 mmol, 1.1 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (20 mL) and then NaBH4 (129 mg, 3.32 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in Ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (1.66 mmol, 1.0 eq) in DMF (20 mL) were added the acid (333 mg, 1.83 mmol, 1.1 eq), DIEA (1.07 g, 8.32 mmol, 5 eq) and HBTU (757 g, 1.99 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (75 mL) and washed with 10% aqHCl (1*50 mL), sat NaHCO3 (1*50 mL) and water (4*50 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25% to 75%)) to give the amide, which was directly used in the next step. The amide was treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product in (263 mg, >95% purity). Mass Spectrum (LCMS, ESI Pos.) Calcd. For C18H26N3O2: 316.0 (M+H), Found 316.0.

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-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Prosetta Antiviral ,Inc.; Selvarajah, Suganya; Paulvannan, Kumar; (58 pag.)US2018/118679; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 175277-11-9, 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. 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows.

Using General Method A, 3-tert-butyl-1-methyl-1H-pyrazole-5-carboxylic acid (0.054 g, 0.3 mmol), Example A1 (0.1 g, 0.25 mmol), triethylamine (0.76 g, 0.75 mmol) and DPPA (0.137 g, 0.5 mmol) were combined and purified by column chromatography (ethylacetate/hexanes) to afford (4-(4-(4-(3-(3-tert-butyl-1-methyl-1H-pyrazol-5-yl)ureido)-3-fluorophenoxy)pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl pivalate as a white solid (0.115 g, 82% yield). 1H NMR (400 MHz, DMSO-d6): delta 8.89 (s, 1H), 8.84 (s, 1H), 8.68 (s, 1H), 8.50 (d, J=5.6 Hz, 1H), 8.19 (t, J=8.8 Hz, 1H), 7.46 (d, J=2.4 Hz, 1H), 7.33 (dd, J=12.0 Hz, 2.8 Hz, 1H), 7.06 (dd, J=8.8 Hz, 1.6 Hz, 1H), 6.97 (dd, J=5.6 Hz, 2.4 Hz, 1H), 6.35 (s, 2H), 6.07 (s, 1H), 3.60 (s, 3H), 1.19 (s, 9H), 1.10 (s, 9H); MS (ESI) m/z: 565.2 (M+H+).

The chemical industry reduces the impact on the environment during synthesis 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; US2008/261961; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 175277-11-9,Some common heterocyclic compound, 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, molecular formula is C9H14N2O2, 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.

46) 3-(tert-butyl)-N-(6-fluoro-2,3-dimethoxybenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (250 mg, 1.36 mmol, 1.0 eq) in toluene (15 mL) was added 2,4-dimethoxybenzyl amine (227 mg, 1.36 mmol, 1.0 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (15 mL) and then NaBH4 (103 mg, 2.72 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in Ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (0.45 mmol, 1.1 eq) in DMF (5 mL) were added the acid (75 mg, 0.407 mmol, 1.0 eq), DIEA (262 mg, 2.04 mmol, 5 eq) and HBTU (205 mg, 0.54 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (20 mL) and washed with 10% aq HCl (1*20 mL), sat NaHCO3 (1*20 mL) and water (4*20 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25% to 75%)) to give the amide, which was directly used in the next step. The amide was treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product. Mass Spectrum (LCMS, ESI Pos.) Calcd. For C18H25FN3O3: 350.0 (M+H), Found 350.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, its application will become more common.

Reference:
Patent; Prosetta Antiviral ,Inc.; Selvarajah, Suganya; Paulvannan, Kumar; (58 pag.)US2018/118679; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 175277-11-9, A common heterocyclic compound, 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, molecular formula is C9H14N2O2, 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.

General procedure: Thearyl acid (1 eq) was dissolved into DMF (1-3 mL/1 mmol) and cooled to 0C. HATU(1.2 eq) and DIPEA (3.5 eq) were then added and reaction was stirred at 0C for5-10 min. The amino acid methyl ester (1 eq) was then added and reaction wasallowed to warm and stir at room temperature overnight. Reaction was pouredinto water,and extracted with EtOAc. The organic layers were combined andwashed with a 1N HCl(aq) solution, sat. NaHCO3 (aq)solution, and brine, dried over MgSO4, and concentrated in vacuo.The crude material was purified by flash chromatography (0-100% EtOAc:Hexanes gradient).9-99%

The synthetic route of 175277-11-9 has been constantly updated, and we look forward to future research findings.

Application of 175277-11-9, 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. 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows.

7) 3-(tert-butyl)-N-(2-fluoro-3-(trifluoromethoxy)benzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (200 mg, 0.96 mmol, 1.0 eq) in toluene (20 mL) was added 2,4-dimethoxybenzyl amine (177 mg, 1.06 mmol, 1.1 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (30 mL) and then NaBH4 (73 mg, 1.92 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in Ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (0.96 mmol, 1.0 eq) in DMF (10 mL) was added the acid (175 mg, 0.96 mmol, 1.0 eq), DIEA (620 mg, 4.8 mmol, 5 eq) and HBTU (440 mg, 1.152 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (200 mL) and washed with 10% aqHCl (1*50 mL), sat NaHCO3 (1*50 mL) and water (4*50 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25% to 75%)) to give the amide, which was directly used in the next step. The amide was treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product in 28% (183 mg, >95% purity). Mass Spectrum (LCMS, ESI Pos.) Calcd. For C17H20F4N3O2: 374.0 (M+H), Found 374.0.

The chemical industry reduces the impact on the environment during synthesis 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid. I believe this compound will play a more active role in future production and life.

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. 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Safety of 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid

11) 3-(tert-butyl)-N-(3-chloro-4-methylbenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of the Acid (257 mg, 1.41 mmol, 1.1 eq) in DMF (10 mL) was added an amine (200 mg, 1.29 mmol, 1.0 eq), DIEA (830 mg, 6.43 mmol, 5 eq) and HBTU (584 mg, 1.54 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (30 mL) and washed with 10% aqHCl (1*25 mL), sat NaHCO3 (1*25 mL) and water (4*25 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (10% to 50% EtOAc in Hexane) to give the amide as a colorless solid in 66% (165 mg, >95% purity). Mass Spectrum (LCMS, ESI Pos.) Calcd. For C17H23ClN3O: 320.0 (M+H), Found 320.0.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

These common heterocyclic compound, 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-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. category: pyrazoles-derivatives

EXAMPLE 7 N-{5-[(2-aminopyrimidin-5-yl)ethynyl]pyridin-3-yl}-3-tert-butyl-1-methyl-1H-pyrazole-5-carboxamide DIPEA (387 mg) was added to a mixture of 5-[(5-aminopyridin-3-yl)ethynyl]pyrimidin-2-amine (Intermediate 11) (211 mg), 3-tert-butyl-1-methyl-1H-pyrazole-5-carboxylic acid (364 mg) and HBTU (642 mg) in DMF (3 mL) and stirred for 65 hours at ambient temperature. The mixture was added dropwise to stirred 1M aqueous sodium hydroxide (100 mL). The solid formed was filtered off, and purified by RPHPLC to give the title compound (121 mg, 32%); 1H NMR (DMSO-d6) 1.28 (s, 9H), 4.02 (s, 3H), 6.97 (s, 1H), 7.19 (s, 2H) 8.32 (t, 1H), 8.42 (d, 1H), 8.47 (s, 2H), 8.79 (d, 1H) 10.39 (br s, 1H); MS m/e MH+376.

The synthetic route of 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid has been constantly updated, and we look forward to future research findings.