Structure of 50413-30-4
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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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CAS No. : | 50413-30-4 |
Formula : | C9H11NO3 |
M.W : | 181.19 |
SMILES Code : | COC(=O)C1=C(N)C=C(OC)C=C1 |
MDL No. : | MFCD06658470 |
Boiling Point : | No data available |
InChI Key : | CEKCJQBZVNIMLD-UHFFFAOYSA-N |
Pubchem ID : | 12919999 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 48.62 |
TPSA ? Topological Polar Surface Area: Calculated from |
61.55 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.72 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.64 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.07 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.06 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.99 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.5 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.77 |
Solubility | 0.308 mg/ml ; 0.0017 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.58 |
Solubility | 0.0473 mg/ml ; 0.000261 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.24 |
Solubility | 1.04 mg/ml ; 0.00573 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) |
No |
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 |
-5.53 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.41 |
* 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 |
---|---|---|
70% | With pyridine; at 20℃; for 16h; | To a stirred solution of compound If-I (7 g, 38.6 mmol) in pyridine (80 ml) was slowly added TsCI (8.8 g, 46.6 mmol) at rt. This solution was further stirred for 16h. The reaction mixture was poured into cold water upon which a solid was formed. The precipitate was filtered off and washed with n-pentane (50 ml) to afford the title compound If-2 as an off-white solid (10.8 g, 70% yield). LCMS [M+H] 336. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.92% | With sulfuric acid; for 24h;Reflux; | To a solution of 2-amino-4-methoxybenzoic acid 33 (5.0 g,0.03 mol) in methanol (50 mL) was added strong sulphuricacid (9 mL). The solution was stirred at reflux for 24 h. Itwas cooled to room temperature and the pH of the mixturewas adjusted to 5~6 with saturated sodium carbonatesolution. The solution was extracted with EA (100 mL*2).The combined organic layers were washed with brine(50 mL), dried over Na2SO4, filtered and concentrated,affording white powder 34 (4.11 g, 75.92%). 34: 1H NMR (400 MHz, CDCl3) 7.81 (d, J = 8.9 Hz, 1 H), 6.25 (dd, J =9.0, 2.5 Hz, 1H), 6.13 (d, J = 2.4 Hz, 1H), 5.80 (s, 2H), 3.86(s, 3H), 3.81 (s, 3H). |
37% | With sulfuric acid;Reflux; | Step a): Methyl 2-amino-4-methoxybenzoate 1000 mg (6.0 mmol) of 2-amino-4-methoxybenzoic acid are reacted according to General Method I. Yield: 400 mg (37% of theory) LC-MS (Method 3): Rt=1.96 min; MS (ESIpos): m/z=182 [M+H]+. 5 mmol of the carboxylic acid are dissolved in 50 ml of methanol, and 5 ml of concentrated sulfuric acid are added. The mixture is heated under reflux for 14-24 h. After cooling to room temperature, the solution is poured onto ice and adjusted to pH 6 using sodium bicarbonate. After addition of 100 ml of dichloromethane, the aqueous phase is separated off and reextracted twice with in each case 50 ml of dichloromethane. The combined organic extracts are dried over sodium sulfate, filtered and concentrated under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide; sodium ethanolate; In methanol; water; | (c) Methyl 4-methoxy-anthranilate One hundred fifty-eight grams (0.89 mol) of 6-methoxy-isatine are suspended in 1300 ml of methanol and mixed with a solution of 54 gm (1.34 mol) of sodium ethoxide in 500 ml of methanol. One hundred eight milliliters (1.07 mol) of 30% hydrogen peroxide are added thereto dropwise, under stirring, and the resulting mixture is stirred for 30 minutes. The contents of the flask are concentrated down to half their volume, mixed with water, and adjusted to a pH of 5 to 6 with glacial acetic acid. After extraction with methylene chloride, the mixture is subjected to suction filtration, kieselguhr being used, and dried with sodium sulfate, and the solvent is distilled off. The residue is recrystallized from petroleum ether/cyclohexane (2:1). M.p: 80-82 C., Yield: 109 gm (67.7% of theory). The following compounds are prepared by analogous procedures: |
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