Structure of 13468-02-5
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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. : | 13468-02-5 |
Formula : | C10H15NO |
M.W : | 165.23 |
SMILES Code : | CN(C)CCOC1=CC=CC=C1 |
MDL No. : | MFCD00040016 |
InChI Key : | RUHVDRGWCIAFLG-UHFFFAOYSA-N |
Pubchem ID : | 26050 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.4 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 50.25 |
TPSA ? Topological Polar Surface Area: Calculated from |
12.47 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.53 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.72 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.63 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.83 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.61 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.86 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.05 |
Solubility | 1.46 mg/ml ; 0.00883 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.6 |
Solubility | 4.17 mg/ml ; 0.0252 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.05 |
Solubility | 0.148 mg/ml ; 0.000893 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 |
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 |
-6.09 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.26 |
* 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 chlorosulfonic acid; In dichloromethane; | Intermediate Example 2 Preparation of [2-(dimethylamino)ethoxy]phenyl-4-sulfonyl chloride 2 g of <strong>[13468-02-5]N,N-dimethyl-N-[(2-phenoxy)ethyl]amine</strong> was dissolved in 10 ml of dichloromethane and 3 ml of chlorosulfonic acid was slowly added under ice cooling. The mixture was stirred at room temperature for 3 hr and poured into ice. Dichloromethane (100 ml) was added and aqueous layer was neutralized by concentrated sodium carbonate solution with keeping temperature under 4 C. Dichloromethane layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. 0.8 g of [2-(dimethylamino)ethoxy]phenyl-4-sulfonyl chloride was obtained. | |
With chlorosulfonic acid; In dichloromethane; at 20℃; for 3.0h;Cooling with ice; | The N, N - dimethyl - N - [(2 - phenoxy) ethyl] amine (1.65 g, 10 . 00 mmol) dissolved in dichloromethane (10 ml) in, under ice bath slowly [...] sulfonic acid (2.5 ml The system for the ice in the pouring, adding dichloromethane (50 ml), separating the organic layer, drying with anhydrous sodium sulfate, concentrated under reduced pressure to obtain the crude intermediate 6 a, directly Used for the next step reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Example 5 - Sodium 4-(2-dimethylaminoethoxy)-benzenesulfonate 7.00 g (42.4 mmol) of dimethyl-(2-phenoxyethyl)-amine were dissolved in 35 mL of glacial acetic acid and cooled in an ice bath. 9.63 g (93.3 mmol) of 95% sulfuric acid were dropped in while maintaining an internal temperature of 10C or lower followed by stirring for 1 hour at room temperature. The solution was concentrated followed by the gradual addition of the concentrated residue to 1 mol/L sodium hydroxide to bring pH10, after which the solution was concentrated and dried. After extracting the residue with methanol, concentrating and drying, the residue was suspended in 100 mL of ethanol followed by cooling and filtration. The filtrate was concentrated and the precipitated crystals were filtered to obtain 8.36 g of the target substance (yield: 74%). 1H-NMR (400 MHz, D2O): delta = 7.68 (d,2H,J=8.8 Hz), 7.01 (d,2H,J=8.8 Hz), 4.33 (t,2H,J=5.0 Hz), 3.53 (t,2H,J=5.2 Hz) 13C-NMR (400 MHz, D2O): delta = 158.12, 133.61, 125.61, 112.90, 61.79, 59.66, 41.70 IR (KBr): nu = 3431, 3097, 2770, 1599, 1180, 1032, 844 cm-1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium hydroxide; In ethanol; water; at 55 - 60℃; for 4.0h; | The phenol 94g (1mol), potassium hydroxide 117.6g (2.1mol) was added 600ml ethanol and stirred to dissolve, temperature at 55 ~ 60 reaction slowly added dropwiseN, N- dimethyl-chloroethane hydrochloride 158g (1.1mol, was dissolved in 300g water), the addition was complete reaction was continued for 4 hours; the reaction was completed, recovering ethanol, then extracted twice with dichloromethane, combined, washed with water and concentrated to give an oil 142g XI, a yield of 86.0%; |
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