Structure of 1092350-27-0
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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. : | 1092350-27-0 |
Formula : | C9H6ClFO2 |
M.W : | 200.59 |
SMILES Code : | O=C1CCOC2=C1C=C(Cl)C=C2F |
MDL No. : | MFCD11518488 |
InChI Key : | WKZNUTWJAOYUBQ-UHFFFAOYSA-N |
Pubchem ID : | 71059488 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-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 | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 45.98 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.99 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.1 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.86 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.03 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.43 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.48 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.75 |
Solubility | 0.358 mg/ml ; 0.00179 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.28 |
Solubility | 1.05 mg/ml ; 0.00522 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.76 |
Solubility | 0.0351 mg/ml ; 0.000175 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 |
-6.03 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) |
2.05 |
* 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 trichlorophosphate; at 0 - 80℃; for 2.0h; | 6.5. Synthetic Method A; Preparation of 8-chloro-6-fluoro-4H-thieno[3,2-c]chromene-2-carboxylic acid <strong>[1092350-27-0]6-chloro-8-fluorochroman-4-one</strong> 1 (5 g, 24.9 mmol) was added dropwise to a solution of phosphorous oxychloride (2.3 mL, 24.9 mmol) in 15 mL of DMFat 0 C. The reaction mixture was stirred at 0 C. for 30 minutes then heated to 80 C. for 1.5 hours. Reaction was then cooled to room temperature and quenched with 1N NaOAc solution and extracted with dichloromethane (2×25 mL). The organic layer was concentrated in vacuo and carried to the next step without further purification. | |
With trichlorophosphate; at 0 - 80℃; for 2.0h; | 1) At 0C,6-Chloro-8-fluorochroman-4-one 1 (5 g, 24.9 mmol)Dissolved in 15 mL of dimethylformamide (N,N-Dimethylformamide, DMF for short),Phosphoryl chloride (2.3 mL, 24.9 mmol) was added dropwise,Obtain the mixture M51; 2) The mixture M51 obtained in S410 is stirred at 0 C. for 30 minutes and heated to 80 C.After cooling for 1.5 hours, cool to room temperature.Obtain the mixture M52; 3) After cooling the mixture M52 obtained from S420 to room temperature,After quenching by adding 1N NaOAc solution,Dichloromethane (2 x 25 mL) was added for extraction,The extracted organic layer was concentrated in vacuo.Get 4,6-dichloro-8-fluoro-2H-chromene-3-carbaldehyde,The next step can be carried out without further purification; |
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