Structure of 3652-90-2
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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. : | 3652-90-2 |
Formula : | C12H8BrN |
M.W : | 246.10 |
SMILES Code : | BrC1=CC2=C(C=C1)C1=CC=CC=C1N2 |
MDL No. : | MFCD09750430 |
InChI Key : | PJRGCJBBXGNEGD-UHFFFAOYSA-N |
Pubchem ID : | 12717089 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 13 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 63.5 |
TPSA ? Topological Polar Surface Area: Calculated from |
15.79 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.23 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.08 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.08 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.5 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.25 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.63 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.62 |
Solubility | 0.00586 mg/ml ; 0.0000238 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.12 |
Solubility | 0.0188 mg/ml ; 0.0000765 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.82 |
Solubility | 0.000375 mg/ml ; 0.00000152 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) |
Yes |
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) |
Yes |
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) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-4.9 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 |
1.0 |
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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.61 |
* 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 |
---|---|---|
Ca. 94% | To a 250 mL three-necked flask, 2-bromocarbazole (6.0 g, 24.38 mmol), sodium hydroxide solution (50%) 4 ml, tetrabutylammonium bromide (0.4 g, 1.24 mmol), and the temperature was stirred for 5 min at room temperature. Bromine hexane (8.045 g, 48 mmol) was added dropwise with a syringe.After 12 h of reaction, the eluent was purified by column chromatography to petroleum ether to afford product 1a as an oil, which, after vacuum drying, weighed 7.57 g (yield about 94%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | 2-Bromocarbazole (20.1 g, 81.6 mmol) and triphenylene-2-boronic acid (23 g, 84.5 mmol) were dissolved in tetrahydrofuran (200 ml), potassium carbonate (K2CO3, potassium carbonate, 40.4 g, 292.8 mmol)Was added to the reaction solution together with water, and the mixture was heated and stirred in a nitrogen state for about one hour.After stirring for one hour, tetrakis (triphenylphosphine) palladium (2.3 g, 1.95 mmol) was added and the mixture was heated with stirring for 6 hoursAfter completion of the reaction, the temperature was lowered to room temperature, and tetrahydrofuran was removed by distillation under reduced pressure, followed by filtration under reduced pressure. The solid obtained by filtration was recrystallized from tetrahydrofuran and ethanol to obtain the formula P1 (28 g, yield 87%) | |
81% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12h;Inert atmosphere; Reflux; | 2-bromo-carbazole (10.0 g, 40.6 mmol),Triphenylene2-boronic acid (13.2 g, 48.5mmol), and potassium carbonate (17.0 g, 123mmol) and tetrahydrofuran (100 mL) and a mixture of water (50 mL) was suspended within. After filling nitrogen,Tetrakis (triphenylphosphine) palladium (0.9 g, 0.7 mmol) was added to the suspension. Under nitrogen, the mixture was stirred for about 12 hours at reflux.After cooling to room temperature the resulting solids were filtered. To a pale yellow solid of the purified using a THF / EtOH P1 of white solid (13 g, 81%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 12h; | General procedure: 3-bromo-9H-carbazole (492.21 mg, 2 mmol), <strong>[267221-88-5]N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline</strong> (965.35 mg, 2.6mmol), potassium carbonate (414.63 g, 3 mmol), terakis(triphenylphosphine)palladium (115.56 mg, 0.1 mmol) were dissolved in amixture solution of tetrahydrofuran (15 ml) and water (5 ml) andrefluxed under nitrogen at 80 C for 12 h. Then, the mixture wasextracted with dichloromethane and washed with water. The organiclayer was dried over anhydrous MgSO4 and the residue was purified on asilica gel column using petroleum ether/dichloromethane mixture (3:1,v/v) as eluent to afford the product as white powder (1180.6 mg, yield:89%). |