Structure of 3-Chloro-6-hydrazinopyridazine
CAS No.: 17284-97-8
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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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CAS No. : | 17284-97-8 |
Formula : | C4H5ClN4 |
M.W : | 144.56 |
SMILES Code : | NNC1=NN=C(Cl)C=C1 |
MDL No. : | MFCD00051740 |
InChI Key : | FXYQRYGWWZKUFV-UHFFFAOYSA-N |
Pubchem ID : | 100787 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H317-H318 |
Precautionary Statements: | P280-P301+P312+P330-P302+P352-P305+P351+P338+P310 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 34.25 |
TPSA ? Topological Polar Surface Area: Calculated from |
63.83 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.96 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.38 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.22 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.32 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.21 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.42 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.4 |
Solubility | 5.72 mg/ml ; 0.0395 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.29 |
Solubility | 7.48 mg/ml ; 0.0518 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.94 |
Solubility | 1.67 mg/ml ; 0.0115 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 |
No |
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 |
-6.91 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 |
1.0 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) |
2.2 |
* 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 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 16h; | A mixture of <strong>[78190-11-1]1-[(benzyloxy)carbonyl]piperidine-3-carboxylic acid</strong> (2.44 g), 3-chloro-6-hydrazinopyridazine (1.34g), WSCD hydrochloride (2.13 g) and methylene chloride (60 ml) was stirred at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure and extracted with ethyl acetate. The extract was washed successively with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resultant reside was combined with acetic acid (80 ml), stirred at 100C for 2 days, and then the solvent was distilled off under reduced pressure. The resultant crude crystals were washed with ethanol, and stirred with heating under reflux in piperidine (10 ml) for 3 hours. The reaction solution was concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: chloroform:methanol=97:3). The resultant colorless solids were combined with ethanol (40 ml) and 10% palladium-carbon (150 mg), and stirred under hydrogen atmosphere at room temperature for 6 hours, and then the catalyst was filtered off. The resultant filtrate was concentrated under reduced pressure to obtain 6-piperidin-1-yl-3-piperidin-3-yl-1,2,4-triazolo[4,3-b]pyridazine (1.18 g) as a colorless amorphous. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of <strong>[78190-11-1]1-[(benzyloxy)carbonyl]piperidine-3-carboxylic acid</strong> (2.44 g), 3-chloro-6-hydrazinopyridazine (1.34g), WSCD hydrochloride (2.13 g) and methylene chloride (60 ml) was stirred at room temperature for 16 hours. The reaction solution was concentrated under a reduced pressure and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under a reduced pressure. The resultant reside was combined with acetic acid (80 ml), stirred at 110C for 2 days, and then the solvent was evaporated under a reduced pressure. The resultant crude crystals were washed with ethanol and stirred with heating under reflux in piperidine (10 ml) for 3 hours. The reaction solution was concentrated under a reduced pressure and purified by a silica gel column chromatography (eluent: chloroform:methanol = 97:3). The resultant colorless solids were combined with ethanol (40 ml) and 10% palladium-carbon (150 mg) and stirred under an atmosphere of hydrogen at room temperature for 6 hours, and then the catalyst was removed by filtration. The resultant filtrate was concentrated under a reduced pressure to obtain 6-piperidin-1-yl-3-piperidin-3-yl-1,2,4-triazolo[4,3-b]pyridazine (1.18 g) as a colorless amorphous substance. |
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