Structure of 186602-93-7
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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. : | 186602-93-7 |
Formula : | C8H8F3NO |
M.W : | 191.15 |
SMILES Code : | OCC1C(N)=CC(C(F)(F)F)=CC=1 |
MDL No. : | MFCD17215842 |
InChI Key : | UBFFHFYJSAIIDB-UHFFFAOYSA-N |
Pubchem ID : | 18697900 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332 |
Precautionary Statements: | P280 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 41.98 |
TPSA ? Topological Polar Surface Area: Calculated from |
46.25 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.63 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.79 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.79 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.95 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.98 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.03 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.36 |
Solubility | 0.83 mg/ml ; 0.00434 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.38 |
Solubility | 0.797 mg/ml ; 0.00417 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.76 |
Solubility | 0.334 mg/ml ; 0.00175 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 |
-6.2 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) |
1.25 |
* 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 |
---|---|---|
100% | With sodium tetrahydroborate; iodine In tetrahydrofuran for 24 h; Heating / reflux | [0069] Representative procedure for the preparation of 2-amino-4- (trifluoromethyl) benzylalcohol (17a): To a suspension of ANTHRANILIC acid 16a (2. 04 g, 10 MMOL), NaBH4 (0. 912 g, 24 MMOL) in THF (10 mL) under N2 at 0 °C was added 12 (2.54 g, 10 MMOL) solution in THF (10 mL) over a period of 10-15 minutes. The resulting reaction mixture was stirred at room temperature for 30 minutes and then at reflux for 24 h. The reaction mixture was cooled to room temperature and MeOH was added very slowly to the mixture till the clear solution was formed. The solvent was removed and the residue was stirred with 20percent KOH (20 mL) at room temperature for 4 h, extracted with CH2CI2 (3 x 100 mL), dried (NA2SO4) and solvent was removed to obtain 1.91 g (100percent) of the requisite ALCOHOL 17A. 1H NMR (CDC13, 300 MHz): 8 7.15 (d, 1H, J = 7.5 Hz), 6.94 (d, 1H, J = 7.5 Hz), 6.91 (s, 1H), 4.71 (s, 2H). |
99% | With borane-THF In tetrahydrofuran at 1.5℃; Inert atmosphere | 5.1.104 6,7-Didehydro-17-methyl-7'-trifluoromethylquinolino[2',3':6,7]morphinan-3,14β-diol (28c) Compound 28c was prepared from compound 22c according to the procedure used to prepare compound 24a. Yield, 83percent; a white needle crystal. Mp 286-287 °C. IR (KBr): 3267, 2936, 1610, 1446, 1326, 1163, 1121, 1060, 910, 754 cm-1. 1H NMR (400 MHz, THF-d8) δ: 1.27-1.40 (1H, m), 2.17-2.32 (2H, m), 2.38-2.47 (1H, m), 2.42 (3H, s), 2.79-2.98 (3H, m), 3.10 (1H, d, J = 17.6 Hz), 3.25 (1H, d, J = 18.0 Hz), 3.51 (1H, d, J = 17.6 Hz), 3.62 (1H, d, J = 17.6 Hz), 6.43 (1H, dd, J = 2.8, 8.4 Hz), 6.72 (1H, d, J = 2.8 Hz), 6.89 (1H, d, J = 8.4 Hz), 7.57 (1H, dd, J = 1.6, 8.4 Hz), 7.77 (1H, s), 7.82 (1H, d, J = 8.4 Hz), 8.20 (1H, d, J = 1.6 Hz), two protons (OH) was not observed. 13C NMR (100 MHz, THF-d8) δ: 25.1, 37.7, 38.0, 40.9, 41.8, 43.7, 47.0, 63.3, 70.4, 113.0, 115.1, 121.8 (q, J = 3.0 Hz), 126.5 (q, J = 272.9 Hz), 127.4 (q, J = 4.5 Hz), 127.5, 129.8 (2C), 130.5, 130.7 (q, J = 32.1 Hz), 133.0, 135.8, 142.2, 146.8, 157.6, 161.2. HRMS (ESI) Calcd for C25H24F3N2O2 [M+H]+: 441.1790. Found: 441.1781. |
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