Structure of 16382-15-3
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 16382-15-3 |
Formula : | C12H13NO2 |
M.W : | 203.24 |
SMILES Code : | O=C(C(N1)=CC2=C1C=CC(C)=C2)OCC |
MDL No. : | MFCD00022703 |
InChI Key : | KMVFKXFOPNKHEM-UHFFFAOYSA-N |
Pubchem ID : | 232919 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H317 |
Precautionary Statements: | P280 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 59.35 |
TPSA ? Topological Polar Surface Area: Calculated from |
42.09 ?2 |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.41 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.97 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.65 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.95 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.19 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.63 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.22 |
Solubility | 0.123 mg/ml ; 0.000606 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.52 |
Solubility | 0.0618 mg/ml ; 0.000304 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.16 |
Solubility | 0.0142 mg/ml ; 0.0000697 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 |
-5.43 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) |
1.88 |
* 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 |
---|---|---|
98% | With N-Bromosuccinimide; In tetrahydrofuran; at 20℃; for 3.5h; | To a solution of S-methyl-lH-indole^-carboxylic acid ethyl ester, 3A (10.17 g, 50.03 mmol) in THF (100 mL) in a room temperature water bath was slowly added NBS (8.91 g, 50.06 mmol). The resulting solution was allowed to stir at room temperature for 3.5 h before water (800 mL) was added. The resulting mixture was allowed to stir at room temperature for 20 min and then filtered. The solid was washed with water (2 x 100 mL), dried in vacuo to provide the crude product 3B as a tan powder (13.8 g, 98percent yield). 1H NMR (500 MHz, CDC13): delta 8.91 (s, IH), 7.44 (q, J= 0.95 Hz 0.63 Hz, IH), 7.28 (d, J= 8.51 Hz, IH), 7.21 7.19 (dd, J= 1.58 Hz 8.51 Hz, IH), 4.46 (q, J= 6.94 Hz 7.25 Hz, 2H), 2.47 (s, 3H), 1.45 (t, J= 7.25 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1% | Ethyl 5-methylindole-2-carboxylate in 1percent yield (2 steps), mp 157-158°; NMR delta(CD3SOCD3) 1.3 (t, 3H), 2.35 (s, 3H), 4.3 (q, 2H), 7.05 (m, 2H), 7.35 (m, 2H), 11.7 (bs, 1H); M/z (+) 203 (M+). | |
B. 5-Methyl-1H-indole-2-carboxylic acid, ethyl ester The title A compound (2.095 g, 9.51 mmol, 1.0 eq) was dissolved in absolute ethanol (9.8 ml, 1M) and hydrochloric acid gas was bubbled through the reaction until it showed no starting material (45 minutes). The reaction solution was then concentrated, dissolved in ethyl acetate, and washed once with aqueous saturated sodium hydrogen carbonate. The organic phase was then dried over sodium sulfate, filtered through magnesium sulfate and concentrated. The residue was chromatographed on silica gel (60 g) eluding with toluene followed by chloroform:hexane (1:4) followed by ether:hexane (2:3) to give the title B compound (1.5187 g). | ||
b Ethyl 5-methylindole-2-carboxylate 130 g of P2 O5 are added to 111 ml of orthophosphoric acid. After cooling, 37 g of the compound from a) are added, and the mixture is heated to 80° C. After the reaction starts, the temperature rises to 130° C. The mixture is cooled and then poured into ice-water and extracted with ethyl acetate. The organic phase is washed with NaHCO3 (1N), H2 O and saturated NaCl solution, dried with Na2 SO4 and concentrated. The product is recrystallized from n-hexane/EtOAc. 11.7 g of product of melting point 158° C. are obtained. |
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