Structure of 1202-25-1
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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. : | 1202-25-1 |
Formula : | C10H13NO2 |
M.W : | 179.22 |
SMILES Code : | O=C(OC)C1=CC=C(N(C)C)C=C1 |
MDL No. : | MFCD00014905 |
InChI Key : | DBQGARDMYOMOOS-UHFFFAOYSA-N |
Pubchem ID : | 70994 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.3 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 51.93 |
TPSA ? Topological Polar Surface Area: Calculated from |
29.54 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.42 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.15 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.54 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.94 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.29 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.87 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.45 |
Solubility | 0.637 mg/ml ; 0.00355 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.4 |
Solubility | 0.709 mg/ml ; 0.00396 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.58 |
Solubility | 0.468 mg/ml ; 0.00261 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 |
-5.87 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) |
1.23 |
* 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 |
---|---|---|
87% | With thionyl chloride; for 5h; | General procedure: To a solution of the benzoic acid derivative (10 mmol) in anhydrous methanol (35 mL)was added dropwise thionyl chloride (1.1 mL, 15 mmol) under vigorous stirring (stirbar). After 5 h, about 25 mL of the methanol was distilled off and the residue was pouredonto 50 mL of ice water. Then saturated aqueous sodium bicarbonate was added withstirring until the evolution of carbon dioxide ceased. The resulting precipitate wascollected and recrystallized from methanol. |
80% | With bromobenzene; at 55 - 60℃; under 3750.38 - 4500.45 Torr; for 8h;Autoclave; | General procedure: benzoic acid (Table 3, entry 1) (1.0 g,0.0081 mol), bromobenzene (0.125 g, 0.0081 mol), 10% palladium on carbon(50% wet) (0.2 g) and methanol (3 mL) were placed in autoclave vessel. Autoclave was pressurized with 1-2 bar of nitrogen followed by 1-2 bar of hydrogen gas and then put under the desired pressure of hydrogen (5-6 bar).The reaction mixtures are then warmed to 55-60 C temperature and stirredfor 4 h at 300 rpm. After reaction, the catalyst was filtered through celite bed.Filtrate was added with water (30 mL). The reaction mixture was extracted with isopropyl acetate (2 15 mL). The combined organic layers were washedwith 5% aqueous sodium bicarbonate solution (2 15 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated under vacuum togive of methyl benzoate product Methyl 4-(dimethyl amino)benzoate: Colorlesssolid: 100-102 oC; 1H NMR (400 MHz, CDCl3):d = 7.96-7.85 (m, 2 H), 6.70-6.59 (m, 2 H), 3.86(s, 3 H), 3.04 (s, 6 H). 13CNMR (100 MHz, CDCl3): delta 40.0, 51.4, 110.7, 117.0, 131.2, 153.2, 167.5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 7 Preparation of methyl 4-dimethylaminobenzoate A stream of dry oxygen was passed through a solution (heated at 30 C.) of 1-(4-dimethylaminophenyl)-2,2,2-trichloroethanol (5.37 g; 20 m. moles) in methanol (50 ml) and a solution of cupric chloride dihydrate (0.05 g; 0.29 m. mole) and 1,10-phenanthroline hydrate (0.15 g; 0.76 m. mole) in methanol (50 ml) in which sodium (0.5 g; 21.7 m. moles) had been dissolved was added portionwise over a period of 11/4 hours. The reaction mixture was diluted with water (200 ml), extracted with ether (3*50 ml) and the combined extracts washed with water. The dried (MgSO4) extract was evaporated to give a pale yellow solid (3.75 g) which was recrystallized from aqueous methanol to give methyl 4-dimethylaminobenzoate (2.7 g; 75%), m.p. 98-99 C. Analysis: Calculated for C10 H13 NO2: C 67.0; H 7.3; N 7.8%. Found: C 66.8; H 7.6; N 7.6%. |
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