Structure of 221615-72-1
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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. : | 221615-72-1 |
Formula : | C15H15NOS |
M.W : | 257.35 |
SMILES Code : | CSC1=CC=C(CC(C2=CC=C(C)N=C2)=O)C=C1 |
MDL No. : | MFCD20267192 |
Boiling Point : | No data available |
InChI Key : | QCTITLPDUACHDS-UHFFFAOYSA-N |
Pubchem ID : | 10131325 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 18 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 75.61 |
TPSA ? Topological Polar Surface Area: Calculated from |
55.26 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.54 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.04 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.54 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.47 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.28 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.17 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.58 |
Solubility | 0.0677 mg/ml ; 0.000263 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.87 |
Solubility | 0.035 mg/ml ; 0.000136 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.78 |
Solubility | 0.000423 mg/ml ; 0.00000164 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) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
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 |
-5.71 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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.06 |
* 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 |
---|---|---|
72% | With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1 h; | To the reaction flask was added llg (4-methylthio) phenylacetic acid,200 mL of anhydrous THF, and the mixture was heated to 65-70 ° C.Maintain T = 65-70 ° C while dropping175 Mll. 0 M t-BuMgCl in THF and5.7g6-methylpyridine-3-carboxylate50 ml of THF solution. Dropping to complete the incubation reaction for 1 hour.Cooling to room temperature, dropping 50ml4M hydrochloric acid quenching reaction, stratification, organic layer and then 50ml4M hydrochloric acid extraction,The aqueous layer was added and the aqueous layer was added with 50 g of sodium hydroxide,Heated to 40-50 ° C for 3 hours, cooled to room temperature,Filtration gave 6.9 g of a pale yellow solid, 72.0percent yield, 97.3percent pure |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.7% | With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1 h; | To the reaction flask was added llg (4-methylthio) phenylacetate, 200 mL of anhydrous THF, and the mixture was heated to 65-70The (: Maintaining T = 65-70 ° C while adding 88 ml of a solution of 1.0 M t-BuMgCl in THF and 5.7 g of 6-methylpyridine-3-carboxylic acid methylEster in 50 ml of THF. Dropping to complete the incubation reaction for 1 hour. Cooled to room temperature, dropping 50 ml of 4 M hydrochloric acid, layered, organic layerAnd then 50ml of 4M hydrochloric acid extraction, the water layer, the water layer by adding 50g sodium hydroxide, heated to 40-50 ° C stirring 3 hours, cooling toAt room temperature and filtered to give 8.3 g of a pale yellow solid, 87.7percent yield, 98.6percent pure |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78.5% | With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1 h; | To the reaction flask was added llg (4-methylthio) phenylacetate, 200 mL of anhydrous THF, and the mixture was heated to 65-70 The (: Maintaining T = 65-70 ° C while adding 88 ml of a solution of 1.0 M t-BuMgCl in THF and 5.7 g of 6-methylpyridine-3-carboxylic acid methyl Ester in 50 ml of THF. Dropping to complete the incubation reaction for 1 hour. Cooled to room temperature, dropping 50 ml of 4 M hydrochloric acid, layered, organic layer And then 50ml of 4M hydrochloric acid extraction, the water layer, the water layer by adding 50g sodium hydroxide, heated to 40-50 ° C stirring 3 hours, cooling to At room temperature and filtered to give 7.4 g of a pale yellow solid, yield 78.5percent, purity 98.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.2 g | With hydrogenchloride In water; acetic acid; toluene at 20℃; | Example-6 Preparation of 1-(6-methyl-3-pyridinyl)-2-[(4-Methylthio)phenyl]ethanone (V) [0068] To compound ( VI) (10 gm) (as per process described above in Example-4) was added a mixture of concentrate hydrochloric acid (75 ml) and Glacial acetic acid (25 ml) After completion of reaction it was cooled to room temperature and extracted with (12 ml) Toluene. [0069] The above reaction mass was added in to a mixture of (31.75 ml) ammonia solution and water (10.00 ml) and stirred. Reaction mass was adjusted to pH between 6.9 to 7.1 using sodium carbonate solution (5percent w/v) at 0-5° C. temperature. It was stirred for 60 minutes and filtered to obtain wet cake. Wet product was washed twice with (10 ml) water. Product wet cake was dissolved in (70 ml) dichloromethane followed by addition of (20 ml) water, stirred for 10 minutes and layers were separated. Aqueous layer was extracted twice with dichloromethane. Combined organic layer containing the product was washed with water (10.00 ml), dried over anhydrous sodium sulphate and purified by activated carbon treatment. [0070] Product layer was concentrated by distilling out dichloromethane at atmospheric pressure to obtain a semi-solid residue. The residue mass was degassed under vacuum for 30 minutes. Isopropyl alcohol (7.5 ml) was added to the mass and it was cooled to 8-10° C. temperature. After stirring for 1 hour at 8-10° C. temperature, it was filtered, and washed with chilled isopropyl alcohol (2.00 ml). The product was dried in a vacuum oven at 45°-50° C. to give dried product (7 gm, purity by HPLC 93.24percent) [0071] Dried product obtained (7 gm) was purified by treatment with methyl iso butyl ketone (17.5 ml). The product slurry was stirred for 30 minutes, filtered and washed with methyl iso butyl ketone (2 ml), and dried under vacuum oven at 40-45° C. temperature. The purified product (5.2 gm) showed HPLC purity 95.40percent. |
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