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CAS No. : | 17404-90-9 | MDL No. : | MFCD01646204 |
Formula : | C8H5ClN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | REUOCJLVDZPJEK-UHFFFAOYSA-N |
M.W : | 164.59 | Pubchem ID : | 11194524 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-H335 | Packing Group: | N/A |
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 |
---|---|---|
With ammonia; water; copper(II) sulfate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium at 120℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane -75 deg C, 2 h; -75 deg C; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane -75 deg C, 2 h; -75 deg C, 1 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With 2,2,6,6-tetramethylpiperidinyl-lithium; acetaldehyde In tetrahydrofuran; hexane -75 deg C, 0.5 h; -75 deg C, 1 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With trichlorophosphate for 240h; Heating; | |
72% | With trichlorophosphate for 144h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Rk. m. LiAlH4 in Bzl. u. Ae. (Kochen) fuehrt zu 3-Chlor-1,4-dihydro-cinnolin; | ||
Rk. m. H2 an Pd-Kohle (NEt3) fuehrt zu 1,4-Dihydro-cinnolin; | ||
Rk. m. 30percentig. H2O2 u. Eg. bei 70grad fuehrt zu 3-Chlor-cinnolin-1-oxid; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3-Amino-cinnolin, konz. HCl, Diazotierung bei 5grad, Ausbeute 27percent (neben Cinnolin-ol-(3) (30percent)); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With n-butyllithium In tetrahydrofuran at 0 - 66℃; for 2.16667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With n-butyllithium In tetrahydrofuran at 0 - 66℃; for 2.16667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 91 percent / nBuLi / tetrahydrofuran / 2.17 h / 0 - 66 °C 2: 66 percent / m-CPBA / CH2Cl2 / 0.5 h / -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 87 percent / nBuLi / tetrahydrofuran / 2.17 h / 0 - 66 °C 2: 76 percent / m-CPBA / CH2Cl2 / 0.5 h / -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 88 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 0.5 h | ||
Multi-step reaction with 3 steps 1: 93 percent / Na / 4 h / 120 °C 2: 25 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C; excess of LTMP, I2 3: HCl / tetrahydrofuran; ethanol / 15 min, 0 deg C; 15 min, RT |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 93 percent / Na / 4 h / 120 °C 2: 88 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 0.5 h 3: 83 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 2 h 4: 12 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / 3.5 h / -70 to -20 deg C | ||
Multi-step reaction with 3 steps 1: 93 percent / Na / 4 h / 120 °C 2: 5 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 0.5 h 3: 12 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / 3.5 h / -70 to -20 deg C | ||
Multi-step reaction with 5 steps 1: 93 percent / Na / 4 h / 120 °C 2: 25 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C; excess of LTMP, I2 3: HCl / tetrahydrofuran; ethanol / 15 min, 0 deg C; 15 min, RT 4: 83 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 2 h 5: 12 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / 3.5 h / -70 to -20 deg C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 25 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C; excess of LTMP, I2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 93 percent / Na / 4 h / 120 °C 2: 88 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 0.5 h 3: 83 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 2 h | ||
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 5 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 0.5 h | ||
Multi-step reaction with 4 steps 1: 93 percent / Na / 4 h / 120 °C 2: 25 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C; excess of LTMP, I2 3: HCl / tetrahydrofuran; ethanol / 15 min, 0 deg C; 15 min, RT 4: 83 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 69 percent / lithium 2,2,6,6-tetramethylpiperidide, I2 / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C; excess of LTMP, I2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 86 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 63 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / 0.5 h / -75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 18 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / 0.5 h / -75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / Na / 4 h / 120 °C 2: 91 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / -75 deg C, 0.5 h; -75 deg C, 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 2: aqueous Na2CO3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran | 13 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1,2,3,6-tetrahydro-1-acetyl-4-piperidinyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester (17) EXAMPLE 13 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1,2,3,6-tetrahydro-1-acetyl-4-piperidinyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester (17) Chloronaphthyridine 16 (8.00 g, 25.7 mmol), and tributylvinylstannane 21 (12.0 g, 28.9 mmol) were dissolved in THF (130 ml) then flushed with nitrogen. Bis(triphenylphosphine)palladium dichloride (0.36 g, 0.5 mmol) and 2,6-di-t-butyl-4-methylphenol (~10 mg) were added to the reaction mixture. This orange solution was refluxed for 36 hours, then cooled and stirred at room temperature for 48 hours. The reaction mixture was evaporated and the residue was purified by chromatography on silica gel with methylene chloride/methanol. The product fractions were recrystallized from THF to give 1.69 g of the title compound. MS-M+ =399, 356, 327, 82, 43 (base). NMR (CDCl3)-ppm 8.69 (s, 1H), 8.65 (dd, 1H, J=1, 15.5 Hz), 2.02-6.92 (m, 1H), 4.43-4.26 (m, H), 3.72 (apparent t, 1H), 3.67-3.61 (apparent t+m, 2H), 2.37-2.84 (m, 1H), 2.18 (m, 3H), 1.41 (5, 7 Hz), 1.37-1.03 (m, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.6 g | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 105℃; for 5h; | 1 Reaction 1 Intermediate 1 (synthesized by the method described in WO2016194784A. 3.8 g), 3-chlorosinnoline (1.0 g), [Tetrakis (triphenylphosphine) palladium (0)] (0.15 g) in a 300 mL eggplant flask. ), 2M tripotassium phosphate aqueous solution (13m)L), toluene (26 mL) and ethanol (13 mL) were added, and the mixture was stirred in an oil bath at 105 ° C. for 5 hours. After cooling to room temperature, the aqueous phase was removed, the remaining liquid was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (neutral silica gel, ethyl acetate / hexane = 1/4). As a result, it was a pale yellow solid. As a result, 2.6 g of intermediate 2 was obtained. |
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