Category: 1082745-50-3

Synthetic Route of 1082745-50-3, These common heterocyclic compound, 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-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.

To a suspension of 0.132 g (0.63mmol) of 5-amino-l-(tetrahydro-pyran-4-yl)-l-H-pyrazole-4- carboxylic acid amide (see PCT patent application WO2010/026214) in dry EtOH (1.5mL), 0.066 g (1.66 mmol) of sodium hydride (60 % suspension in mineral oil) were added at room temperature under nitrogen. After lOmin, 0.181mg (0.945mmol) of Example 13 A were added and the reaction mixture was heated to 140C for 40 min in a microwave oven (Power 100W). The reaction mixture was then diluted with DCM, water was added, organics separated and dried over sodiumsulphate. Organics were evaporated under reduced pressure and the crude purified by flash cromatography (DCM/IPA 98:2) to obtain the title compound as a white solid. (54mg, 32%).HPLC-MS (Method lEh): R, = 8.01 minMS (APCI pos): m/z = 352 (M+H)+

Statistics shows that 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide is playing an increasingly important role. we look forward to future research findings about 1082745-50-3.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEINE, Niklas; EICKMEIER, Christian; FERRARA, Marco; GIOVANNINI, Riccardo; ROSENBROCK, Holger; SCHAENZLE, Gerhard; WO2012/20022; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1082745-50-3,Some common heterocyclic compound, 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, molecular formula is C9H14N4O2, 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 the mixture of 5-amino-1-(tetrahydro-2H-pyran-4-yl)-1 H-pyrazoLe-4-carbox- amide (Intermediate P6) (0.317 g, 1.51 mmol) and ethyl phenoxyacetate (0.333 g, 1.81 mmol) in n-butanoL (30 mL) sodium ethanolate (21%, 2.815 mL, 7.54 mmcl) was added and the whole was heated at reflux for 24 hours. The productwas isolated by extraction with ethyl acetate. Organic Layer was dried with sodium sulphate. After concentration, product was purified by chromatography on silicagel (chloroform/methanol, gradient 99:1 to 96:4). 0.137 g of the title product as an amorphous, colorless solid were obtained (yield 28.4%).1H NMR (300MHz, DMSO-d6): delta 12.37 (s, 1H), 8.09 (s, 1H), 7.31 (dd, J = 10.7, 5.4Hz, 2H), 7.13 – 6.90 (m, 3H), 5.03 (s, 2H), 4.88 – 4.68 (m, 1H), 3.95 (dd, J = 11.4, 3.6 Hz, 2H), 3.49 (t, J = 11.2 Hz, 2H), 2.09 (qd, J = 12.3, 4.5 Hz, 2H), 1.80 (dd, J = 12.4, 2.3 Hz, 2H).13C NMR (75 MHz, DMSO-d6): delta 157.72, 157.69, 155.39, 150.96, 134.23, 129.51,121.41, 114.87, 104.88, 67.20, 65.97, 53.18, 31.96.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, its application will become more common.

Reference:
Patent; CELON PHARMA S.A.; MOSZCZY?SKI-P?TKOWSKI, Rafa?; BOJARSKI, ?ukasz; STEFANIAK, Filip; WIECZOREK, Maciej; DUBIEL, Krzysztof; LAMPARSKA-PRZYBYSZ, Monika; WO2014/16789; (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. 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H14N4O2

To a solution of 5-amino-1-tetrahydropyran-4-yl-pyrazole-4-carboxamide (4.78 g, 22.7mmol) in dry THF (200 mL) was added methyl 2-(4-bromophenyl)acetate (7.81 g, 34.1 mmol) and t-BuOK (1 M, 45 mL) in THF (45 mL). The mixture was stirred at 80C for 16 hours. Themixture was quenched with water (30 mL) and adjusted with HCI (iN, aqueous) to pH=7. The mixture was filtered. The filter cake was washed with water (20 mL x 3) to give 6-[(4- bromophenyl)methyl]-1-tetrahydropyran-4-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one (5 g).

According to the analysis of related databases, 1082745-50-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (87 pag.)WO2018/73251; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1082745-50-3,Some common heterocyclic compound, 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, molecular formula is C9H14N4O2, 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 0.8 g (3.805 mmol) of 5-amino-l-(tetrahydro-pyran-4-yl)-l-H-pyrazole-4- carboxylic acid amide (see PCT patent application WO2010/026214) in 8 mL anhydrous EtOH , 0.457 g (19.6 mmol) of sodium hydride (60 % suspension in mineral oil) were added at room temperature under nitrogen. After 1 h under stirring, 1.2g (11.42mmol) of trans- cyclobutane-l,2-dicarbonitrile were added and the reaction mixture was heated to 140C for 45 min in a microwave oven. The solvent was removed under reduced pressure. The residue was dissolved in DCM, water was added and phases were separated. Organic layers were dried over sodium sulphate and evaporated under reduced pressure. The crude was purified by flash cromatography (Cy/EtOAc from 80/20 to 100%) to obtain the title compound as yellow solid. (0.64g, 55%)HPLC-MS(MethodlEh):R,=6.21minMS (APCI): m/z = 300 (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 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEINE, Niklas; EICKMEIER, Christian; FERRARA, Marco; GIOVANNINI, Riccardo; ROSENBROCK, Holger; SCHAENZLE, Gerhard; WO2012/20022; (2012); 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. 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, A new synthetic method of this compound is introduced below., Product Details of 1082745-50-3

Example 11 B (0.1 g, 0.48 mmol) was mixed with polyphosphoric acid (1.0 g) and 2- (trifluoromethoxy)phenylacetic acid (248 mg, 1.9 mmol) was added. The mixture was heated to 1200C during 16 hours. Temperature was lowered to 200C and the pH value was adjusted to 7 by addition of ammonia (30 % solution in water). The aqueous phase was extracted with dichloromethane (2 x 20 ml_) and the organic phase was dried over sodium sulphate. The crude mixture was purified by flash chromatography. Eluent: hexane/ethyl acetate 40/60. Obtained 23.5 mg (16 %) as a white solid HPLC-MS (I E ) Rt: 6.77 min MS (APCI pos): m/z = 305 (M+H)+

The synthetic route of 1082745-50-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/121919; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1082745-50-3, These common heterocyclic compound, 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-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.

To a suspension of 0.132 g (0.63mmol) of 5-amino-l-(tetrahydro-pyran-4-yl)-l-H-pyrazole-4- carboxylic acid amide (see PCT patent application WO2010/026214) in dry EtOH (1.5mL), 0.066 g (1.66 mmol) of sodium hydride (60 % suspension in mineral oil) were added at room temperature under nitrogen. After lOmin, 0.181mg (0.945mmol) of Example 13 A were added and the reaction mixture was heated to 140C for 40 min in a microwave oven (Power 100W). The reaction mixture was then diluted with DCM, water was added, organics separated and dried over sodiumsulphate. Organics were evaporated under reduced pressure and the crude purified by flash cromatography (DCM/IPA 98:2) to obtain the title compound as a white solid. (54mg, 32%).HPLC-MS (Method lEh): R, = 8.01 minMS (APCI pos): m/z = 352 (M+H)+

Statistics shows that 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide is playing an increasingly important role. we look forward to future research findings about 1082745-50-3.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEINE, Niklas; EICKMEIER, Christian; FERRARA, Marco; GIOVANNINI, Riccardo; ROSENBROCK, Holger; SCHAENZLE, Gerhard; WO2012/20022; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1082745-50-3,Some common heterocyclic compound, 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, molecular formula is C9H14N4O2, 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 5-amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide (1.0 g, 4.76 mmol) and triethyl orthoformate (7.72 g, 47.6 mmol) in DMSO (20 mL) was added Cs2CO3 (3.1 g 9.5 mmol). The mixture was stirred at 130 C. for 36 hours. The mixture was diluted with water (100 mL) and extracted with DCM (30 mL*3). The organic layer was washed with water (30 mL*2) and dried over Na2SO4. The organic layer was evaporated under vacuum. The mixture was purified by silica gel chromatography (DCM: MeOH from 20:1 to 5:1) to give 6-methyl-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (560 mg, 50% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, its application will become more common.

Reference:
Patent; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Marigo, Mauro; Kehler, Jan; Rasmussen, Lars Kyhn; (27 pag.)US2017/291901; (2017); 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. 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H14N4O2

To the mixture of 5-amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide (Intermediate P6, 0,301 g, 1,55 mmol) and ethyl (2-chlorophenoxy)-acetate (Intermediate P16, 1.663 g, 7.75 mmol) in dry tetrahydrofuran (16 mL) 5 eq. of IM soLution of potassium tert-butanolate in tetrahydrofuran were addedand the whole was heated at reflux for 18 hours. The crude product was isoLated by extraction with ethyl acetate, organic layer was washed with brine and dried with sodium sulphate. The compound was purified by chromatography on silica gel (hexane/acetone, gradient from 100:0 to 0:100). 95 mg of the titLe product were obtained as an amorphous soLid (yield 29.2%).1H NMR (300MHz, DMSO-d6): delta 12.37(5, 1H), 8.09 (s, 1H), 7.47 (m, 1H), 7.31 (m,1H), 7.25 (m, 1H), 7.01 (m, 1H), 5.14 (s, 2H), 4.87 (m, 1H), 3.94 (m, 2H), 3.47 (m, 2H), 2.09 (m, 2H), 1.77 (m, 2H).MS-ESI: (m/z) calculated for C17H18C1N4O3 [M+H]+: 361 .79, found 361 .8.

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; CELON PHARMA S.A.; MOSZCZY?SKI-P?TKOWSKI, Rafa?; BOJARSKI, ?ukasz; STEFANIAK, Filip; WIECZOREK, Maciej; DUBIEL, Krzysztof; LAMPARSKA-PRZYBYSZ, Monika; WO2014/16789; (2014); 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. 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H14N4O2

To a suspension of 0.132 g (0.63 mmol) of 5-amino-1-(tetrahydro-pyran-4-yl)-1-H-pyrazole-4-carboxylic acid amide (see PCT patent application WO2010/026214) in dry EtOH (1.5 mL), 0.066 g (1.66 mmol) of sodium hydride (60% suspension in mineral oil) were added at room temperature under nitrogen. After 10 min, 0.181 mg (0.945 mmol) of Example 13A were added and the reaction mixture was heated to 140 C. for 40 min in a microwave oven (Power 100W). The reaction mixture was then diluted with DCM, water was added, organics separated and dried over sodiumsulphate. Organics were evaporated under reduced pressure and the crude purified by flash chromatography (DCM/IPA 98:2) to obtain the title compound as a white solid. (54 mg, 32%).HPLC-MS (Method 1Eh): Rt=8.01 minMS (APCI pos): m/z=352 (M+H)+ The enantiomers of the title compound were separated by HPLC using a chiral stationary phase.Method for Enantioseparation:Semipreprative Conditions: HPLC semipreparative system: Waters 600 pump; column: Daicel chiralcel OJ-H, 250 mmx20 mm, 5.0 mum; eluent: hexane/EtOH85:15; flow rate: 15 mL/min, Temperature: 25 C.; UV Detection: 254 nm Analytical ConditionsHPLC apparatus type: Agilent 1100; Method 6.1; column: Daicel chiralcel OJ-H, 250 mmx4.6 mm, 5.0 mum; eluent: hexane/EtOH85:15; flow rate: 1 mL/min, Temperature: 25 C.; UVDetection: 254 nm

The synthetic route of 1082745-50-3 has been constantly updated, and we look forward to future research findings.