Structure of 108714-73-4
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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. : | 108714-73-4 |
Formula : | C15H15N |
M.W : | 209.29 |
SMILES Code : | NC1=CC(C(C)(C)C2=C3C=CC=C2)=C3C=C1 |
MDL No. : | MFCD09953790 |
InChI Key : | GUTJITRKAMCHSD-UHFFFAOYSA-N |
Pubchem ID : | 22617093 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 68.79 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.02 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.31 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.74 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.58 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.47 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.77 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.38 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.05 |
Solubility | 0.0187 mg/ml ; 0.0000894 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.98 |
Solubility | 0.022 mg/ml ; 0.000105 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.6 |
Solubility | 0.000529 mg/ml ; 0.00000253 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) |
Yes |
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 |
-4.92 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 |
1.0 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) |
2.17 |
* 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 |
---|---|---|
31.9 g | With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In toluene; for 3h;Inert atmosphere; Reflux; | The compound <strong>[13438-50-1]3-bromofluoranthene</strong> (30 g, 98 mmol) and 2-amino-9,9-dimethylfluorene (20.5 g, 98 mmol) were completely dissolved in 200 ml of toluene in a nitrogen atmosphere and then NaOt-Bu (11.3 g, 117.6 mmol) The mixture was stirred while increasing the temperature. After refluxing began, Bis (tri-tert-butylphosphine) palladium (0) (0.5 g, 0.98 mmol) was slowly added dropwise. After 3 hours, the reaction was terminated, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure, and then subjected to column purification to obtain 31.9 g of intermediate A |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate; In toluene; at 100℃; for 20h; | 5 grams (g) of <strong>[50548-45-3]1-bromodibenzo[b,d]furan</strong> (Intermediate (a)), 6.4 g of 9,9-dimethyl-9H-fluoren-2-amine (Intermediate (b)), 6.4 g of potassium tert-butoxide (KtOBu), 0.3 g of P(tBu)3, and 0.4 g of Pd2 (dba)3 were diluted in toluene, followed by stirring at a temperature of 100 C. under reflux. After a 20-hour lapse, the temperature was lowered to room temperature. Subsequently, the reaction was terminated utilizing water. An organic layer was extracted therefrom three times utilizing ethyl acetate. Then, the organic layer was dried utilizing anhydrous magnesium sulfate, followed by filtration under reduced pressure. The obtained residue was separated and purified through column chromatography to thereby obtain 6.5 g of Intermediate 1-1 (yield: 86%). The compound thus obtained was identified by liquid chromatography-mass spectrometry (LC-MS). C27H21NO: calc'd: M+375.16 foun'd: 375.26 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In toluene; at 105 - 110℃; for 2h;Inert atmosphere; | <strong>[26608-06-0]3-bromodibenzofuran</strong> (10.0 g, 40.5 mmol),2-bromo-9,9-dimethylhydrazine (9.3 g, 44.5 mmol),Tris(dibenzylideneacetone)dipalladium (0.4 g, 0.4 mmol),2-Dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (0.4 g, 0.8 mmol) and sodium tert-butoxide (5.8 g, 60.7 mmol) were added to toluene (100 mL).Heated to 105-110 C under nitrogen protection,After stirring for 2 hours; cooling to room temperature, the reaction solution was washed twice with water, dried over magnesium sulfate, filtered, and then filtered, and the filtrate was passed through a silica gel column, and the solvent was removed under reduced pressure. The crude product was recrystallized and purified using dichloromethane/n-heptane system. The pale yellow solid intermediate VII-B (12.1 g, 80%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Under nitrogen protection, 2-bromo-7-adamantyl-9,9-dimethylfluorene 82.797mmol, 2-amino-9,9-dimethylfluorene 82.797mmol, toluene 675mL,248.391mmol of sodium tert-butoxide, stir, heat up to 70 C, slowly add Pd2dba3 0.82797mmol, s-PHOS 1.6560mmol, after the addition, continue to warm to 105 C and reflux for 4h, then lower the temperature to 70 C, add 4- Brominated biphenyl 81.141 mmol, continued to warm to 105 C. and refluxed for 6 h. After the reaction was completed, the temperature was reduced, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried, filtered, and concentrated. After passing through the column with a mixed solvent of dichloromethane and n-heptane, it was recrystallized to LC> 99.95%. Compound 9 was dried. Yield: 53%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 95℃; for 24h; | 9,9-dimethyl-9H-fluoren-2-amine (6.5g, 0.031mol / sigma aldrich), Pd (pph3) 4 (1.8g, 0.0015mol), in Intermediate 1-3 (10.0g, 0.031mol),TOL 300ml was added to potassium carbonate (12.8g, 0.0935mol) and reacted at 95 C for 24 hours. After the completion of the reaction, the mixture was cooled and separated by H20: MC, followed by column purification (n-Hexane: MC), to obtain 11.0 g (yield 79%) of intermediate 7-1. |