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CAS No. : | 65202-50-8 | MDL No. : | MFCD08694876 |
Formula : | C6H5ClN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FPKXYXKLOWAIOX-UHFFFAOYSA-N |
M.W : | 172.57 | Pubchem ID : | 12379801 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 38.32 |
TPSA : | 52.08 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.53 cm/s |
Log Po/w (iLOGP) : | 1.65 |
Log Po/w (XLOGP3) : | -0.25 |
Log Po/w (WLOGP) : | 0.92 |
Log Po/w (MLOGP) : | 0.56 |
Log Po/w (SILICOS-IT) : | 1.38 |
Consensus Log Po/w : | 0.85 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.02 |
Solubility : | 16.3 mg/ml ; 0.0946 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.39 |
Solubility : | 71.0 mg/ml ; 0.412 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.34 |
Solubility : | 0.789 mg/ml ; 0.00457 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.8 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
79% | for 2.5 h; Reflux | B. A mixture of 6-hydroxypyridazine-3-carboxylic acid methyl ester obtained above and phosphorous oxychloride were carefully heated to reflux temperature and maintained there for 2.5 h. The reaction mixture was then cooled and evaporated in vacuo to remove excess phosphorylchloride, and the residue was then poured into ice water. The precipitate was collected by filtration, washed with saturated NaHCO3 and water, and dried under vacuum to yield the product as a yellow solid (4.359 g, 79percent yield). |
50% | With trichlorophosphate In toluene at 120℃; | POCl3 (5.60g, 0.036mol) was added to a solution of Example 65A (2.8g, 0.018mol) in toluene at room temperatureand the mixture was heated to 120°C and stirred for 2 hours. The solvent was evaporated to dryness, water (20mL)was added and the mixture was extracted with ethyl acetate (15mL 3 3). The combined organic layer was washed withbrine, dried over sodium sulfate, filtered and the filtrate was evaporated. The residue was purified by column chromatographyto give the title compound (1.5g, yield 50percent). 1H NMR (CHLOROFORM-d, Bruker Avance 400 MHz) ppm 8.17(d, J=8.8 Hz, 1H), 7.68 (d, J=8.8 Hz, 1H), 4.09 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With methanol In dichloromethane at 0℃; for 1 h; | PREPARATION 58 6-Chloro-pyridazine-3-carboxylic acid methyl ester Oxalyl chloride (1.14mL, 13.09mmol), was added dropwise to an ice-cold suspension of 6-CHLORO-PYRIDAZINE-3-CARBOXYLIC acid [(1.9g, 11.9mmol), J. Het. Chem. 29 (6), 1583-92,. 1992] in a mixture of DICHBROMETHANE (50ML) AND N, N-dimethylformamide (1 drop) and the mixture was stirred for 1 hour at room temperature. The reaction mixture was then evaporated under reduced pressure and the residue was diluted with dichloromethane (30ML) and cooled to 0°C. Methanol (485μL, 11.9mmol) was added and the mixture was stirred at 0°C for 1 hour. Sodium hydrogen carbonate solution was then added to the reaction mixture and the aqueous layer was separated and extracted with DICHLOROMETHANE (X2).. The combined organic solutions were washed with brine, - dried over-sodium sulfate and concentrated in. vacuo to afford the title compound as a white solid in 65percent yield, 1.33g. .-IHNMR (CDCL3, 400MHZ) No.: 4.09 (s, 3H),-7. 67 (d, 1H), 8.16(d, 1H). MS APCI+ m/z 173 [MH]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | for 2.5 h; Heating / reflux | B. A mixture of 6-hydroxypyridazine-3-carboxylic acid methyl ester obtained above and phosphorous oxychloride were carefully heated to reflux and maintained there for 2.5 h. The reaction mixture was then cooled and evaporated in vacuo to remove excess phosphorylchloride, and the residue was then poured into ice water. The precipitate was collected by filtration, washed with saturated NaHCO3 and water, and dried under vacuum to yield the product as a yellow solid (4.359 g, 79percent yield). |
68% | at 110℃; for 5 h; | A sample of S48 (333 mg, 2.16 mmol) was dissolved in POCl3 (3.2 mL) and warmed at 110 0C for 5 h. Upon disappearance of starting material, the solution was cooled to room temperature and diluted with EtOAc. The organic layer was poured onto ice and extracted. The organic layer was subsequently washed with saturated aqueous NaCl. The aqueous layer was back extracted with EtOAc and the combined organic phase was dried over Na2SO4 and filtered. The solution was evaporated and the residue was purified by flash chromatography (50percent EtOAc-hexanes) to afford the title compound as a yellowish solid (254 mg, 68percent): 1H NMR (CDCl3, 400 MHz) δ 8.17 (d, IH, J = 8.8 Hz), 7.68 (d, IH, J = 8.8 Hz), 4.08 (s, 3H); 13C NMR (CDCl3, 100 MHz) 6 159.5, 150.8, 129.8, 128.9, 53.7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: for 3 h; Heating / reflux Stage #2: at 20℃; |
A solution of 6-chloro-pyridazine-3-carboxylic acid (700 mg, 4.53mmol) in thionyl chloride (15 ml) was refluxed for 3 h. The reaction was cooled to ambient temperature and evaporated to dryness. Sodium methoxide (244 mg, 4.53 mmol) in [MEOH] (20 ml) was added to the residue and the solution was stirred on at room temperature (rt). [H2O] was added and the mixture was extracted three times with DCM. The combined organic phases were dried and concentrated. Flashchromatography [(SI02,] Heptane/EtOAc 1: 1) afforded 560 mg (72percent) of the title compound. [1H] NMR [(CDC13),] 5 (ppm): 4.09 (s, 3 H), 7.69 (d, 1 H), 8. 18 (d, 1 H). [LC-MS] [(M++1)] : 173 and 175 (3: 1). |
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