Structure of 934-26-9
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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. : | 934-26-9 |
Formula : | C4H6ClN5 |
M.W : | 159.58 |
SMILES Code : | NC1=CC(Cl)=NN=C1NN |
MDL No. : | MFCD19201394 |
InChI Key : | ZKDLFTXWBSJIKO-UHFFFAOYSA-N |
Pubchem ID : | 250005 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 38.65 |
TPSA ? Topological Polar Surface Area: Calculated from |
89.85 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.79 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.25 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.19 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.24 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.47 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.03 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.36 |
Solubility | 6.89 mg/ml ; 0.0432 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.7 |
Solubility | 3.2 mg/ml ; 0.0201 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.59 |
Solubility | 4.09 mg/ml ; 0.0256 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 |
-7.1 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) |
2.53 |
* 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 sodium hydroxide; | Step B: 4-amino-6-chloropyridazine A stirred solution of 1.2 grams of <strong>[934-26-9]3-hydrazino-4-amino-6-chloropyridazine</strong> and 15 ml of aqueous 8percent sodium hydroxide solution is heated under reflux for 30 minutes. The reaction mixture is treated with decolorizing carbon and filtered. The filtrate is neutralized with aqueous 50percent acetic acid and the resultant precipitate is collected by filtration. The filter cake is recrystallized from water to yield 0.8 gram of 4-amino-6-chloropyridazine, m.p. 153°-154.5° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With hydrazine hydrate; In ethanol; at 100℃; for 3.0h; | Step 112.2: 6-chloro-3-hydrazinylpyridazin-4-amine To a stirred suspension of 3,6-dichloropyridazin-4-amine (Step 112.1) (1.49 g, 9.09 mmol) in EtOH (15 mL) was added hydrazine hydrate (11.04 mL, 227 mmol) and the resulting mixture was heated up and stirred at 100 C. for 3 hr. The reaction was cooled down to RT and concentrated under reduced pressure. The crude product was triturated with water (25 mL) to afford the title product (478 mg, 3 mmol, 33% yield) as yellow solid. tR: 0.24 min (LC-MS 2); ESI-MS: 160 [M+H]+ (LC-MS 2); ESI-MS: 158 [M-H]- (LC-MS 2). |
33% | With hydrazine hydrate; In ethanol; at 100℃; for 3.0h; | To a stirred suspension of 3,6-dichloropyridazin-4-amine (Step 112.1) (1.49 g, 9.09 mmol) in EtOH (15 mL) was added hydrazine hydrate (11.04 mL, 227 mmol) and the resulting mixture was heated up and stirred at 100 00 for 3 hr. The reaction was cooled down to RT andconcentrated under reduced pressure. The crude product was triturated with water (25 mL) to afford the title product (478 mg, 3 mmol, 33% yield) as yellow solid. tR: 0.24 mm (LC-MS 2); ESIMS: 160 [M+H] (LC-MS 2); ESl-MS: 158 [M-H] (LC-MS 2). |
With hydrazine hydrate; In ethanol; water; | Step A: 3-hydrazino-4-amino-6-chloropyridazine A stirred solution of 2.0 grams of 4-amino-3,6-dichloropyridazine and 2.5 ml of hydrazine hydrate in 20 ml of ethanol is heated under reflux for three hours. After this time water is added to the reaction mixture and the resultant precipitate collected by filtration. The filter cake is recrystallized from ethanol to yield 2.3 grams of 3-hydrazino-4-amino-6-chloropyridazine; m.p. 190 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium acetate; at 170℃; for 4.0h;Microwave irradiation; Sealed tube; | Step 112.3: 6-chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-amine A MW vial was charged with <strong>[934-26-9]6-chloro-3-hydrazinylpyridazin-4-amine</strong> (Step 112.2) (475 mg, 2.98 mmol) and potassium acetate (467 mg, 4.76 mmol) in AcOH (5 mL). The MW vial was sealed and the resulting mixture was heated up and stirred at 170 C. for 4 hr. The reaction was cooled down to RT and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (NH3 1%/CH2Cl2/MeOH 1-3%) to afford the title product (450 mg, 2.451 mmol, 82% yield). tR: 2.32 min (HPLC 1); tR: 0.55 min (LC-MS 2); ESI-MS: 184 [M+H]+ (LC-MS 2); ESI-MS: 182 [M-H]- (LC-MS 2); Rf=0.45 (CH2Cl2/MeOH 9:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | at 170℃; for 4.0h;Microwave irradiation; | A MW vial was charged with <strong>[934-26-9]6-chloro-3-hydrazinylpyridazin-4-amine</strong> (Stepi 12.2) (475 mg, 2.98 mmol) and potassium acetate (467 mg, 4.76 mmol) in AcOH (5 mL). The MW vial was sealed and the resulting mixture was heated up and stirred at 170°C for 4 hr. The reaction was cooled down to RT and concentrated under reduced pressure. The crude product was purified by silicagel column chromatography (NH3 1percent/CH2CI2/MeOH 1-3percent) to afford the title product (450 mg,2.451 mmol, 82percent yield). tR. 2.32 mm (HPLC 1); tR. 0.55 mm (LC-MS 2); ESl-MS: 184 [M+H] (LC-MS 2); ESl-MS: 182 [M-H] (LC-MS 2); R = 0.45 (CH2CI2/MeOH 9:1). |