Structure of 6238-12-6
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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. : | 6238-12-6 |
Formula : | C11H11NO |
M.W : | 173.21 |
SMILES Code : | CC1=CC=NC2=CC(OC)=CC=C12 |
MDL No. : | MFCD11655579 |
InChI Key : | LVJHDVPCJRWNNZ-UHFFFAOYSA-N |
Pubchem ID : | 13685551 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.18 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 53.2 |
TPSA ? Topological Polar Surface Area: Calculated from |
22.12 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.18 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.58 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.55 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.78 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.91 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.4 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.04 |
Solubility | 0.157 mg/ml ; 0.000907 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.69 |
Solubility | 0.351 mg/ml ; 0.00203 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.21 |
Solubility | 0.0107 mg/ml ; 0.0000615 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 |
-5.52 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) |
1.2 |
* 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 triphenylphosphine; lithium chloride;bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); at 20 - 120℃; for 16h; | 4 g of triphenylphosphine, 5.3 g of lithium chloride, 14 ml of tetramethyltin and 2.1 g of bis(triphenylphosphine)palladium(II) chloride are added to a solution of 6 g of <strong>[1070879-27-4]4-bromo-7-methoxyquinoline</strong> in 100 ml of DMF, under an inert atmosphere of argon at a temperature in the region of 20° C. The reaction medium is heated at a temperature in the region of 120° C. for 16 hours. After cooling, the insoluble material is filtered off. The filtrate is concentrated under reduced pressure. The residue obtained is taken up in 300 ml of EtOAc and 300 ml of water. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The oil obtained is taken up in 300 ml of EtOAc and 300 ml of water and then acidified with hydrochloric acid to pH 1. The aqueous phase is basified with sodium hydroxide to pH 10 and then extracted with 300 ml of EtOAc. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure to give 2.7 g of 4-methyl-7-methoxyquinoline, the characteristics of which product are as follows: 1H NMR spectrum (300 z, (CD3)2SO d6, delta in ppm): 2.65 (s: 3H); 3.94 (s: 3H); 7.23 (broad d, J=4.5 Hz: 1H); 7.28 (dd, J=9 and 3 Hz: 1H); 7.40 (d, J=3 Hz: 1H); 8.01 (d, J=9 Hz: 1H); 8.58 (d, J=4.5 Hz: 1H). Mass IE m/z=173 M+. base peak m/z=158 (M-CH3)+ m/z=143 (M-CH2O)+. m/z=130 (m/z=158-CO)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With selenium(IV) oxide; In 1,4-dioxane; at 20 - 80℃; for 21h; | A mixture of 1.9 g of selenium oxide dissolved in 35 ml of dioxane is added dropwise to a solution of 2.7 g of <strong>[6238-12-6]4-methyl-7-methoxyquinoline</strong> in 35 ml of dioxane preheated to 65° C. At the end of the addition, the brown suspension is heated to a temperature in the region of 80° C. for 5 hours. The reaction medium is stirred for 16 hours at a temperature in the region of 20° C. The greenish suspension is suction-filtered and then washed with EtOAc. The filtrate is concentrated under reduced pressure. The suspension obtained is crystallized from isopropyl ether to give 1.54 g of 7-methoxyquinoline-4-carbaldehyde. 1H NMR spectrum (300 MHz, (CD3)2SO d6, delta in ppm): 3.99 (s: 3H); 7.48 (dd, J=9 and 3 Hz: 1H); 7.57 (d, J=3 Hz: 1H); 7.90 (d, J=4.5 Hz: 1H); 8.89 (d, J=9 Hz: 1H); 9.19 (d, J=4.5 Hz: 1H); 10.52 (s: 1H). Mass IC m/z=188 MH+ base peak |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With N-Bromosuccinimide; In dichloromethane; at 20℃; for 3h;Inert atmosphere; | To a stirred solution of <strong>[6238-12-6]7-methoxy-4-methylquinoline</strong> (1.00 g, 5.77 mmol) in DCM (25 mL) is added NBS (1.23 g, 6.91 mmol). The resulting suspension is stirred for 3 d at RT. The RM is diluted with DCM and washed with saturated aqueous NaHCO3 and brine, dried over MgSO4 and then purified by FC to give the desired product as a yellow solid (1.1 18 g, 77percent). LC-MS A: tR = 0.51 min; [M+H]+ = 252.00. |
A429970 [1807542-80-8]
7-Methoxy-4-methylquinoline hydrochloride
Similarity: 0.98
A429970 [1807542-80-8]
7-Methoxy-4-methylquinoline hydrochloride
Similarity: 0.98