Structure of 1118-66-7
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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 1118-66-7 |
Formula : | C5H9NO |
M.W : | 99.13 |
SMILES Code : | CC(/C=C(N)/C)=O |
MDL No. : | MFCD00043715 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.4 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 28.58 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.09 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.18 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.43 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.44 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.02 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.05 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.4 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.66 |
Solubility | 21.7 mg/ml ; 0.219 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.9 |
Solubility | 12.4 mg/ml ; 0.125 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.25 |
Solubility | 55.4 mg/ml ; 0.558 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) |
No |
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 |
-6.6 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) |
2.11 |
* 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 |
---|---|---|
52% | In ethanol; | EXAMPLE 17 3-acetyl-4-(3-bromo-4-fluorophenyl)-2-methyl-4,6,7,8-tetrahydro[1,6]naphthyridin-5(1H)-one The product from Example 1C (0.610 g, 5.40 mmol), 3-bromo-4-fluorobenzaldehyde (1.10 g, 5.40 mmol) and 2-amino-2-pentene-4-one (0.535 g, 5.40 mmol) in ethyl alcohol (25 mL) were stirred in a sealed tube at 80° C. for 12 hours. The reaction mixture was cooled to ambient temperature and filtered to provide the title compound as a white solid (2.05 g, 52percent yield). MS (APCI+) m/z 379 (M+H)+; 1H NMR (DMSO-d6) delta9.01 (s, 1H), 7.41 (dd, 1H, J=6.6, 1.8 Hz), 7.24 (dd, 1H, J=8.7, 8.7 Hz), 7.18 (ddd, 1H, J=7.2, 5.1, 2.1 Hz), 7.02 (d, 1H, J=1.8 Hz), 4.98 (s, 1H), 3.17-3.09 (m, 2H), 2.47-2.34 (m, 214),2.31 (s, 3H), 2.09 (s, 3H); Anal. Calcd for C17H16N2O2FBr: C, 53.84; H, 4.25; N, 7.39. Found: C, 53.74; H, 4.36; N, 7.50. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With boron trifluoride diethyl etherate; In dichloromethane; at 130℃; for 0.216667h;Microwave irradiation; | General procedure: A substituted amino unsaturated ketone (2, 1 mmol) and boron trifluorid ediethyletherate (10 mol%) in dichloromethane (5 ml) were added to a solution of substituted phenacyl bromide (1, 1 mmol) and the mixture was irradiated with microwaves for 10-16 min at 130C (250 W). After completion of the reaction, asindicated by TLC analysis, the reaction mixture was poured on to crushed ice, neutralized with sodium bicarbonate, extracted with ethyl acetate, and the extract was concentrated by rotary evaporation. The residue was purified by silica gel column chromatography with hexane-EtOAc (7:3) as eluent to afford the pyrrole derivatives 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With acetic acid; In isopropyl alcohol; at 100℃; for 19h; | A mixture of thianaphthene-3-carboxaldehyde (0.106 g, 0.65 mmol), <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropanoate</strong> (0.071 g, 0.72 mmol) and 4-amino-3-penten-2-one (0.088 g, 0.61 mmol) and acetic acid (0.035 mL) in isopropylalcohol (1.5 mL) was heated to 100C and left to stir for 19 hours. The mixture was allowed to cool to RT and was then treated with saturated aqueous sodium bicarbonate solution (10 mL). The solid was filtered off, washed with water, dried and purified by column chromatography (4:1 hexane: ethyl acetate) affording a fine yellow solid (0.075 g, 44 %). 1H-NMR (400 MHz, DMSO-d6) δ = 0.76 (s, 2H), 0.96 (d, 2H), 2.12 (s, 3H), 2.33 (s, 3H), 2.69 (s, 1H), 3.58 (s, 3H), 5.43 (s, 1H), 7.15 (s, 1H), 7.31 (s, 1H), 7.38 (s, 1H), 7.90 (s, 2H), 8.05 (d, 1H). HPLC-MS: Rt 4.302 min, m/z 234.1 (MH+-133). (0600) A second reaction product was isolated by column chromatography: Example J1-a: Dimethyl 4-(benzo[b]thiophen-3-yl)-2,6-dicyclopropyl-1,4-dihydropyridine-3,5-dicarboxylate (0601) 1H-NMR (400 MHz, DMSO-d6) δ = 0.56 (s, 2H), 0.82 (s, 2H), 0.90 (d, 2H), 1.04 (s, 2H), 2.56 (m, 2H), 3.55 (s, 5H), 5.37 (s, 1 H), 7.05 (s, 1 H), 7.11 (s 1 H), 7.32 (t, 1 H), 7.39 (t, 1H), 7.90 (d, 1 H), 7.98 (s, 1 H). HPLC-MS: Rt 4.935; m/z 276.1 (MH+). |