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CAS No. : | 114722-60-0 | MDL No. : | MFCD24559424 |
Formula : | C10H7N3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BNKZAGNSCZCLIN-UHFFFAOYSA-N |
M.W : | 185.18 | Pubchem ID : | 57346845 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
* + POCl3 (2 h Sieden) --> 4-Chlor-pyrazolo<2,3-a>chinoxalin.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Pyrazolo<2,3-a>chinazolin-4-ol-2-carbonsaeure + Cu-Pulver in Chinolin, Δ.; | ||
4-Hydroy-pyrazolo<2,3-a>chinoxalin-carbonsaeure-(2) + Cu-Pulver in Chinolin (Er- hitzen auf 160-180grad, zuletzt 240-250grad).; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With sodium t-butanolate In diethylene glycol dimethyl ether at 140℃; for 24h; Glovebox; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sodium hydride In N,N-dimethyl acetamide for 48h; Reflux; | 4.27. Pyrazolo[1,5-a]quinoxalin-4(5H)-one (17a) A mixture of 16a (7 g, 34.1 mmol) and sodium hydride (2.04 g,51 mmol) in dimethylacetamide (253 mL) was heated to reflux for48 h. The sodium hydride was neutralized with saturated aqueousNH4Cl solution and the reaction mixture was then concentrated invacuum. The residue was collected by filtration, washed withdistilled water, and dried. The compound is obtained as a grey solid(74% yield). C10H7N3O. MW: 185.18 g/mol. Mp 260-263 °C. 1H NMRδ (ppm, 300 MHz, DMSO-d6) 7.15 (d, 1H, CH 3), 7.29 to 7.42 (m, 3H),8.07 to 8.14 (m, 2H). 13C NMR δ (ppm, 75 MHz, DMSO-d6) 106.13,116.00, 124.88, 125.39, 126.00, 126.39, 132.05, 153.34, 156.59,160.38. MS (ESI+ , QTof, m/z): 186.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate; N,N-diethylaniline / 0.25 h / 130 °C / Microwave irradiation; Sealed tube 2: ethanol / 0.5 h / 150 °C / Microwave irradiation; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate; N,N-diethylaniline / 0.25 h / 130 °C / Microwave irradiation; Sealed tube 2: ethanol / 0.5 h / 150 °C / Microwave irradiation; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: trichlorophosphate; N,N-diethylaniline / 0.25 h / 130 °C / Microwave irradiation; Sealed tube 2: ethanol / 0.5 h / 150 °C / Microwave irradiation; Sealed tube 3: N-Bromosuccinimide / chloroform / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N-diethylaniline; trichlorophosphate at 130℃; for 0.25h; Microwave irradiation; Sealed tube; | 4.30. N-methylpyrazolo[1,5-a]quinoxalin-4-amine (19a) Phosphorus oxychloride (6 mL) and N,N-diethylaniline (0.85 mL,5.4 mmol) were added to 17a (0.5 g, 2.7 mmol) in a microwaveadaptedvial and sealed. The reaction was irradiated at 130 °C for15 min. The reaction mixture was neutralized with saturatedaqueous Na2CO3 solution (50 mL). The solution was extracted withdichloromethane (3 50 mL). The organic layer was dried overMgSO4 and concentrated to dryness under vacuum to give 18a. Amixture of 18a (1 g, 4.9 mmol) and methylamine (4 mL in 33% ofabsolute ethanol solution) in dry ethanol (14.4 mL) was submittedto microwave irradiation in a sealed tube at 150 C for 30 min. Thesolvent was removed under reduced pressure, and the residue wasdissolved in CH2Cl2 (20 mL). The organic fraction was washed withsaturated aqueous solution NaHCO3 (20 mL), dried over Na2SO4,and concentrated under reduced pressure. The product was purifiedby column chromatography on silica gel eluted with CH2Cl2/MeOH (98:2). The compound is obtained as a white solid (82%yield). C11H10N4. MW: 198.22 g/mol. Mp 154-155 °C. 1H NMRδ (ppm, 400 MHz, DMSO-d6) 3.04 (s, 3H, CH3), 7.11 (d, 1H, CH 3,J=4 Hz), 7.28 (td, 1H, CH 7, J=8 Hz), 7.40 (td, 1H, CH 8, J=8 Hz), 7.60(dd, 1H, CH 9, J=8 Hz), 7.86 (s, 1H, NH), 8.07 (d, 1H, CH 2, J=4 Hz),8.18 (dd, 1H, CH 6, J=8 Hz). 13C NMR δ (ppm, 100 MHz, DMSO-d6)106.13,116.00,124.88,125.39,126.00,126.39,132.05,153.34,156.59,160.38. MS (ESI+ , QTof, m/z): 199.0 [M+H]+. HRMS: m/z calculated for C11H11N4 199.0984, found 199.0985. |
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