Structure of 773887-09-5
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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. : | 773887-09-5 |
Formula : | C10H11BrN2 |
M.W : | 239.11 |
SMILES Code : | CC(C)C1=C2NN=CC2=CC(Br)=C1 |
MDL No. : | MFCD13177024 |
InChI Key : | WHZLVUPLAGPFMC-UHFFFAOYSA-N |
Pubchem ID : | 21102197 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.3 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 58.37 |
TPSA ? Topological Polar Surface Area: Calculated from |
28.68 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.02 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.37 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.45 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.78 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.61 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.04 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.89 |
Solubility | 0.0307 mg/ml ; 0.000128 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.65 |
Solubility | 0.0535 mg/ml ; 0.000224 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.59 |
Solubility | 0.0061 mg/ml ; 0.0000255 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
Yes |
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 |
-5.37 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 |
0.0 |
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) |
1.87 |
* 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 |
---|---|---|
4.2 g (74%) | 5-Bromo-7-isopropyl-1H-indazole A flame-dried round bottom flask was charged with 4-bromo-2,6-diethylphenyldiazo-t-butyl sulfide (7.94 g, 24 mmol) and potassium t-butoxide (27 g, 10 equiv). A stir bar was added and the mixture placed under nitrogen. To this was added dry dimethylsulfoxide (70 mL). The mixture was stirred vigorously overnight at room temperature. The reaction mixture was carefully poured into a mixture of crushed ice (250 mL) and 10% hydrochloric acid (120 mL). The resulting suspension was collected by filtration and washed severally with water. The solid was collected and dried in vacuo to give 4.2 g (74%) of the desired product. LC/MS: tR=1.73 min, 241.06 (MH)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.1 g (92%) | With hydrogenchloride; sec.-butyllithium; sodium hydrogencarbonate; In tetrahydrofuran; N-methyl-acetamide; cyclohexane; | 7-Isopropyl-1H-indazole-5-carbaldehyde <strong>[773887-09-5]5-Bromo-7-isopropyl-1H-indazole</strong> (3.1 g, 12.1 mmol) and sodium hydride (0.34 g, 1.1 equiv.) were weighed into a flame-dried round-bottom flask containing a magnetic stir bar. Under a nitrogen atmosphere at room temperature, dry tetrahydrofuran (18 mL) was added. The mixture was stirred at room temperature for 15 min, during which time it became homogeneous. The stirred mixture was cooled to -78 C. and a solution of sec-butyllithium in cyclohexane (1.4M, 20 mL, 2.2 equiv.) was added over several minutes. After 1 h at -78 C., dimethylformamide (3.0 mL) was slowly added and the mixture allowed to warm to room temperature overnight. The solution was cooled to 0 C. and carefully treated with 1 N hydrochloric acid (35 mL). After a few minutes, solid sodium bicarbonate was added until a pH of 9-10 was attained. The two layers were separated and the aqueous phase washed twice with ethyl acetate. The combined organic layers were washed with water (2*), brine (2*), dried over sodium sulfate, and concentrated. Column chromatography gave 2.1 g (92%) of pure material. LC/MS: tR=1.15 min, 189.12 (MH)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.1% | With acetic acid; sodium nitrite; In water; | Compound 15b (1.1 g, 4.8 mmol) was dissolved in 15 mL of acetic acid, and 2 mL of sodium nitrite (400 mg,Aqueous solution of 5.8 mmol) was stirred overnight. After the reaction solution is concentrated, a saturated sodium hydrogencarbonate solution is added.Ethyl acetate (20 mL × 3) was extracted, and the organic phase was combined, washed with saturated sodium chloride and dried over sodium sulfate.Concentrated under reduced pressure,The residue was purified by eluent system B using a CombiFlash rapid preparation apparatus.The title product 15c (670 mg, yield: 58.1%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.1% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100.0℃; for 3.0h;Inert atmosphere; | Compound 15c (400 mg, 1.67 mmol), Compound 1b (638 mg, 2.51 mmol),[1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (122 mg, 0.17 mmol) and potassium acetate (492 mg, 5.02 mmol)The mixture was separately added to 20 mL of 1,4-dioxane, and reacted at 100 C for 3 hours. Diatomaceous earth filtration,Ethyl acetate (20 mL × 2) was washed and concentrated under reduced pressure.The residue was purified by eluent system B using a CombiFlash rapid preparation apparatus.The title product 15d (360 mg, yield: 75.1%) was obtained. |
A443566 [1031417-71-6]
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