Structure of 17285-36-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 17285-36-8 |
Formula : | C4H2Cl2N2O |
M.W : | 164.98 |
SMILES Code : | ClC1=CC(=O)NN=C1Cl |
MDL No. : | MFCD04971420 |
InChI Key : | RWDZPWHMUXKPMN-UHFFFAOYSA-N |
Pubchem ID : | 320690 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 34.88 |
TPSA ? Topological Polar Surface Area: Calculated from |
45.75 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.24 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.17 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.08 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.05 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.5 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.41 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.09 |
Solubility | 1.33 mg/ml ; 0.00807 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.73 |
Solubility | 3.1 mg/ml ; 0.0188 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.78 |
Solubility | 0.272 mg/ml ; 0.00165 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.48 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.84 |
* 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 acetic acid; at 100.0℃; for 12.0h; | A solution of 3,4,6-trichloropyridazine (20.0 g, 109.04 mmol) in HOAc (100 mL) was heated at 100 °C for 12 h, at which time TLC indicated the reaction had gone to completion. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography (petroleum ether : Ethyl acetate = 1 : 1 ) to give the title compounds (11.2 g, 63percent yield) (1 : 1 ratio of regioisomers) as a white solid. LCMS M/Z (M+H) 165. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.7 g | With acetic acid; at 130.0℃; for 2.0h; | 3,4,6-Trichloropyridazine (12 g, 65.4 mmol) in acetic acid (45 mL) was heated at 130 °C for two hours. After cooling to room temperature, the reaction mixture was poured into ice water (200 mL). The solid was collected by filtration to give 3.7 g of the title compound. |
3.7 g | With acetic acid; at 130.0℃; for 2.0h; | Example 18A 5,6-dichloropyridazin-3(2H)-one [0749] 3,4,6-Trichloropyridazine (12 g, 65.4 mmol) in acetic acid (45 mL) was heated at 130° C. for two hours. After cooling to room temperature, the reaction mixture was poured into ice water (200 mL). The solid was collected by filtration to give 3.7 g of the title compound. |
3.7 g | With acetic acid; at 130.0℃; for 2.0h; | 3,4,6-Trichloropyridazine (12 g, 65.4 mmol) in acetic acid (45 mL) was heated at 130 °C for two hours. After cooling to ambient temperature, the reaction mixture was poured into ice water (200 mL). The solid was collected by filtration to give 3.7 g of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
360 mg | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; at 85.0℃; for 16.0h;Inert atmosphere; | A. 5-Chloro-6-(3-methoxyphenyl)pyridazin-3(2H)-one. To a 50-mL round-bottom flask was placed a solution of <strong>[17285-36-8]5,6-dichloro-2,3-dihydropyridazin-3-one</strong> (990 mg, 6.00 mmol) and (3- methoxyphenyl)boronic acid (900 mg, 5.91 mmol) in EtOH (45 mL) and water (9 mL) then Na2C03 (1062 mg, 10.02 mmol) and Pd(PPh3)4 (288 mg, 0.24 mmol) were added under nitrogen. The reaction was stirred for 16 h at 85°C, cooled to rt, and concentrated under reduced pressure. The residue was purified by column chromatography eluting with EtO Ac/petroleum ether (2: 1) affording 360 mg of the title compound as a white solid. Mass Spectrum (LCMS, ESI pos): Calcd. for CiiH10ClN2O2+: 237.0 (M+H); Found: 237.0. |
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