Category: 82560-12-1

Adding a certain compound to certain chemical reactions, such as: 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, 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 82560-12-1, SDS of cas: 82560-12-1

To a solution of methyl-4-iodo-2-methoxybenzoate (10.0 g, 34.2 mmol) in toluene (90 mL) was added 3-tert-butyl-1H-pyrazol-5-amine (5.24 g, 37.7 mmol) followed by (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (870 mg, 1.08 mL, 6.85 mmol) and potassium carbonate (14.9 g, 108 mmol). The mixture was purged with N2, copper(I) iodide (326 mg, 1.71 mmol) was added and the reaction mixture was heated at reflux under N2 for 18 hr. The mixture was cooled to RT and was partitioned between EtOAc (100 mL) and water (3×150 mL). The organic layer was separated and washed with aq. citric acid solution (1% w/v, 150 mL) followed by water (150 mL), and was then dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 330 g, EtOAc in isohexane, 0-100%, gradient elution) to afford methyl 4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)-2-methoxybenzoate as a buff coloured solid (3.62 g, 35%); Rt 1.93 min (Method 2); m/z 304 (M+H)+ (ES+).

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Reference:
Patent; King-Underwood, John; Hardy, George; Murray, Peter John; Williams, Jonathan Gareth; Onions, Stuart Thomas; US2013/29990; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

82560-12-1, name is 3-Amino-5-tert-butylpyrazole, 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. Recommanded Product: 82560-12-1

To a solution of 5-amino-3-tert-butylpyrazole (3.93 g, 28.2 mmol) in CH2Cl2 (140 mL) was added di-tert-butyl dicarbonate (6.22 g, 28.5 mmol) in one portion. The resulting solution was stirred at room temp. for 13 h, then diluted with EtOAc (500 mL). The organic layer was washed with water (2 x 300 mL), dried (MgSO4) and concentrated under reduced pressure. The solid residue was triturated (100 mL hexane) to give the desired carbamate (6.26 g, 92%): mp 63-64 C; TLC Rf (5% acetone/95% CH2Cl2); 1H-NMR (DMSO-d6) delta 1.15 (s, 9H), 1.54 (s, 9H), 5.22 (s, 1H), 6.11 (s, 2H); FAB-MS m/z ((M+H)+).

The synthetic route of 82560-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharmaceuticals Corp.; EP1047418; (2005); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 82560-12-1,Some common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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.

3-Tert-butyl-1H-pyrazol-5-amine (J-III) (1 eq., 40 g) was dissolved in dilute HCI (120 ml of HCI in 120 ml of water) and mixed dropwise with NaNO2 (1.03 eq., 25 g in 100 ml) at 0 – 5 0C over a period of 30 min. After stirring for 30 minutes, the reaction mixture was neutralised with Na2CO3. A diazonium salt obtained by reaction of KCN (2.4 eq., 48 g), water (120 ml) and CuCN (1.12 eq., 31 g) was added dropwise to the reaction mixture within 30 min and the mixture was stirred for a further 30 min at 75 0C. After complete reaction, the reaction mixture was extracted with EE (3 x 500 ml), the combined organic phases were dried over sodium sulphate and the solvent was removed under vacuum. The purification (SiO2, 20 % EE/hexane) of the residue by column chromatography produced a white solid (J-IV) (6.5 g, 15.1 % yield).

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

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; SCHIENE, Klaus; DE VRY, Jean; DAMANN, Nils; FRORMANN, Sven; LESCH, Bernhard; LEE, Jeewoo; KIM, Yong-Soo; KIM, Myeon-Seop; WO2010/127856; (2010); 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. 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

A solution of Intermediate 55a (2.64 g, 6.50 mmol), 3-tert-butyl-1H-pyrazole-5-amine (997 mg, 7.1 mmol) and trans-N,N?-dimethylcyclohexane-diamine (185 mg, 0.33 mmol) was formed in toluene (25 mL). Potassium carbonate (1.9 g, 13.7 mmol) was added and the mixture degassed by bubbling nitrogen through it. Copper(I) iodide (64.0 mg, 1.30 mmol) was added and the mixture was refluxed at 110 C. for 24 h. The solvent was evaporated under reduce pressure and the residue was partitioned between EtOAc/Water and extracted with EtOAc. The combined organics were dried over Na2SO4, filtered and evaporated. Purification by FCC eluting with a gradient of 0-50% EtOAc in cyclohexane gave the title compound (1.72 g, 64%). LCMS (Method 3): Rt 3.69 min, m/z 418 [MH+].

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.

Reference:
Patent; CHIESI FARMACEUTICI S.p.A.; Alcaraz, Lilian; Hurley, Christopher; Cridland, Andrew Peter; Jennings, Andrew Stephen Robert; US2014/364412; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

82560-12-1,Some common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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.

A5. General Method for the Synthesis of BOC-Protected Pyrazoles; 5-Amino-3-tert-butyl-N1-(tert-butoxycarbonyl)pyrazole; To a solution of 5-amino-3-tert-butylpyrazole (3.93 g, 28.2 mmol) in CH2Cl2 (140 mL) was added di-tert-butyl dicarbonate (6.22 g, 28.5 mmol) in one portion. The resulting solution was stirred at room temp. for 13 h, then diluted with EtOAc (500 mL). The organic layer was washed with water (2×300 mL), dried (MgSO4) and concentrated under reduced pressure. The solid residue was triturated (100 mL hexane) to give the desired carbamate (6.26 g, 92%); mp 63-64 C.; TLC Rf (5% acetone/95% CH2Cl2); 1H-NMR (DMSO-d6) delta 1.15 (s, 9H), 1.54 (s, 9H), 5.22 (s, 1H), 6.11 (s, 2H); FAB-MS m/z ((M+H)+).

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

Reference:
Patent; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Paulsen, Holger; Riedl, Bernd; Scott, William J.; Smith, Roger A.; Wood, Jill E.; Hatoum-Mokdad, Holia; Johnson, Jeffrey; Lee, Wendy; Redman, Aniko; Sibley, Robert; Renick, Joel; US2007/244120; (2007); 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. 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, A new synthetic method of this compound is introduced below., Quality Control of 3-Amino-5-tert-butylpyrazole

3-Tert-butyl-1H-pyrazol-5-amine (J-III) (1 eq., 40 g) was dissolved in dilute HCI (120 ml of HCI in 120 ml of water) and mixed dropwise with NaNO2 (1.03 eq., 25 g in 100 ml) at 0 – 5 0C over a period of 30 min. After stirring for 30 minutes, the reaction mixture was neutralised with Na2CO3. A diazonium salt obtained by reaction of KCN (2.4 eq., 48 g), water (120 ml) and CuCN (1.12 eq., 31 g) was added dropwise to the reaction mixture within 30 min and the mixture was stirred for a further 30 min at 75 0C. After complete reaction, the reaction mixture was extracted with EE (3 x 500 ml), the combined organic phases were dried over sodium sulphate and the solvent was removed under vacuum. The purification (SiO2, 20 % EE/hexane) of the residue by column chromatography produced a white solid (J-IV) (6.5 g, 15.1 % yield).

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.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; SCHIENE, Klaus; DE VRY, Jean; DAMANN, Nils; FRORMANN, Sven; LESCH, Bernhard; LEE, Jeewoo; KIM, Yong-Soo; KIM, Myeong-Seop; WO2010/127855; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 82560-12-1, These common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, 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.

3-(tert-butyl)-lH-pyrazole-5-amine (503 mg, 3.61 mmol), Intermediate 30b (915 mg, 3.44 mmol), copper (I) iodide (32.8 mg, 0.172 mmol), trans- N,N’-dimethylcyclohexane- l ,2-diamine (97.8 mg, 0.688 mmol) and K2CO3 (998 mg, 7.22 mmol) were weighed in a round bottom flask, sealed with a septum and evacuated and purged with Ar 3 times. Xylene (4 ml, sparged with Ar for 45 min), was then introduced to the flask and the brown suspension was heated to 150C for 90 min. The reaction was cooled, diluted with EtOAc (10 mL), water (10 mL) and saturated aqueous NH4OH solution (5 mL). The aqueous layer was extracted with EtOAc (2 x 10 mL), and the combined organics washed with brine (15 mL), dried over Na2SO4, filtered, concentrated in vacuo and subjected to FCC eluting with 0 – 4% MeOH/EtOAc to afford the title compound as a pale yellow solid (457 mg, 48%). LCMS (Method 4): Rt 2.81 min, m/z 278 [MH+].

Statistics shows that 3-Amino-5-tert-butylpyrazole is playing an increasingly important role. we look forward to future research findings about 82560-12-1.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; PANCHAL, Terry Aaron; JENNINGS, Andrew Stephen Robert; CRIDLAND, Andrew Peter; HURLEY, Christopher; WO2014/194956; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 82560-12-1, A common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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 microwave vial was charged with 3-tert butyl- lH-pyrazole-5 -amine (1.03 g, 7.39 mmol), copper (I) iodide (70.3 mg, 0.37 mmol) and potassium carbonate (2.14 g, 15.5 mmol) and the vial sealed with a septum, evacuated and purged with argon. Trans- N,N’-dimethylcyclohexane-l,2-diamine (210 mg, 1.48 mmol) was then added, then a solution of Intermediate Vc (4.26 g, 8.86 mmol) in toluene (7.5 mL, degassed with argon) was added, and the reaction was subjected to microwave irradiation (150 C for 1 h). The reaction mixture was then filtered through Celite, and the filtrate concentrated in vacuo. Purification by FCC, eluting with 0 – 60% EtOAc/cyclohexane, to afford the title compound (2.41 g, 66%). LCMS (Method 3) Rt 4.68 min, m/z 493, 495 [MH+].

The synthetic route of 82560-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; HURLEY, Christopher; CRIDLAND, Andrew, Peter; JENNINGS, Andrew, Stephen, Robert; WO2014/195402; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 82560-12-1, 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. 82560-12-1, name is 3-Amino-5-tert-butylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 3-tert-butyl-1H-pyrazol-5-amine 7 (0.139 g, 1 mmol), methyl ester 6 (0.199 g, 1 mmol) and DMSO (2 mL) was stirred at ambient temperature during 2 h. After complete disappearance of the starting materials (monitored by TLC), the solid formed was collected by filtration and washed with MeOH/H2O (1/2) (3 × 2 mL), to afford compound 8. Orange solid, 76% yield; m.p: 241-242 C. FTIR nu (cm-1): 3371 (NH), 3316 (NH), 3117, 2955, 1705 (CO), 1625 (CN), 1532 and 1323 (NO2), 1122 (C-O); 1H NMR (CDCl3) delta 1.39 (s, 9H, tBu), 3.95 (s, 3H, OCH3), 5.98 (s, 1H, Pz-CH), 8.06 (d, 1H, J = 9.1 Hz), 8.13 (dd, 1H, J = 9.1 Hz, J = 1.8 Hz), 8.94 (d, 1H, J = 1.8 Hz), 10.07 (bs, 1H, Pz-NH) ppm, the aniline NH is missing; 13C NMR (CDCl3) delta 30.0 (tBu), 31.2 (Cq, tBu), 52.2 (OCH3), 94.9 (Pz-CH), 117.2, 119.5 (Cq), 128.9, 132.1 (Cq), 136.2, 144.3 (Cq), 148.0 (Cq), 154.6 (Cq), 165.5 (CO) ppm. MS (EI) m/z (%): 318 (100, M+), 287 (15, M – CH3). Anal. Calcd. for C15H18N4O4: C, 56.60; H, 5.70; N, 17.60. Found: C, 56.54; H, 5.83; N, 17.46.

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-Amino-5-tert-butylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Abonia, Rodrigo; Cortes, Edwar; Insuasty, Braulio; Quiroga, Jairo; Nogueras, Manuel; Cobo, Justo; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4062 – 4070;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 82560-12-1,Some common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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.

A5. General Method for the Synthesis of BOC-Protected Pyrazoles 5-Amino-3-tert-butyl-N1-(tert-butoxycarbonyl)pyrazole: To a solution of 5-amino-3-tert-butylpyrazole (3.93 g, 28.2 mmol) in CH2Cl2 (140 mL) was added di-tert-butyl dicarbonate (6.22 g, 28.5 mmol) in one portion. The resulting solution was stirred at room temp. for 13 h, then diluted with EtOAc (500 mL). The organic layer was washed with water (2*300 mL), dried (MgSO4) and concentrated under reduced pressure. The solid residue was triturated (100 mL hexane) to give the desired carbamate (6.26 g, 92%): mp 63-64 C.; TLC Rf (5% acetone/95% CH2Cl2); 1H-NMR (DMSO-d6) delta 1.15 (s, 9H), 1.54 (s, 9H), 5.22 (s, 1H), 6.11 (s, 2H); FAB-MS m/z ((M+H)+).

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

Reference:
Patent; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Paulsen, Holger; Riedl, Bernd; Scott, William J.; Smith, Roger A.; Wood, Jill; Hatoum-Mokdad, Holia; Lee, Wendy; Redman, Aniko; Johnson, Jeffrey; Sibley, Robert; US2012/46290; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics