Structure of 189281-66-1
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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. : | 189281-66-1 |
Formula : | C7H4Cl2FNO2 |
M.W : | 224.02 |
SMILES Code : | O=C(C1=CC(F)=C(Cl)N=C1Cl)OC |
MDL No. : | MFCD02180634 |
InChI Key : | WADLLLSMEPLCNO-UHFFFAOYSA-N |
Pubchem ID : | 2775354 |
GHS Pictogram: |
![]() |
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 | 0.14 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 45.49 |
TPSA ? Topological Polar Surface Area: Calculated from |
39.19 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.02 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.73 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.73 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.94 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.94 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.47 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.16 |
Solubility | 0.156 mg/ml ; 0.000694 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.21 |
Solubility | 0.139 mg/ml ; 0.000621 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.62 |
Solubility | 0.0537 mg/ml ; 0.00024 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 |
-5.73 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 |
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) |
1.98 |
* 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 |
---|---|---|
97% | In methanol; at 20℃; for 1h; | [00670] Intermediate 73b: methyl 2-chloro-5-fluoro-6-methoxy-pyridine-3-carboxylate[00671] Sodium methoxide (1 .86mL, 11.91 mmol) was added to methyl 2,6-dichloro-5-fluoro-pyridine-3-carboxylate (1 .8g, 8.O3mmol) in Methanol (9mL) and the resultant mixture was left to stir for 1 hour. To the mixture was added EtOAc (20 mL) and water (20 mL), the layers were separated and the organ ics extracted using EtOAc (3 x 20 mL). Organic fractions were collected, dried (Na2SO4), filtered and reduced in vacuo to afford the desired product methyl 2-chloro-5-fluoro-6- methoxy-pyridine-3-carboxylate (1 .72g, 7.83mmol, 97% yield) as an orange solid.1H NMR (CDCI3,400MHZ) Olppm: 7.92 (1H, d, J= 9.6 Hz), 4.09 (3H, 5), 3.92 (3H, 5). MS Method 2: RT: 1.71 mm, 220.0 mlz [M+H] |
With methanol; at 20℃; for 0.666667h; | To a solution of 1.5 g of methyl 2,6-dichloro-5-fluoronicotinate in 12 mL of methanol, a solution of 1.3 g of 28% sodium methoxide/methanol in 3 mL of methanol was dropped, and the mixture was stirred at room temperature for 40 minutes. Thereto were added water and ethyl acetate, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.2 g of methyl 2-chloro-5-fluoro-6-methoxynicotinate as a white solid. 1H-NMR (CDCl3) delta: 3.92 (3H, s), 4.09 (3H, s), 7.92 (1H, d, J = 9.8 Hz) |
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