Structure of 171364-80-0
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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. : | 171364-80-0 |
Formula : | C14H19BO4 |
M.W : | 262.11 |
SMILES Code : | COC(=O)C1=CC=C(C=C1)B1OC(C)(C)C(C)(C)O1 |
MDL No. : | MFCD02179438 |
InChI Key : | REIZEQZILPXYKS-UHFFFAOYSA-N |
Pubchem ID : | 2773500 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 19 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.5 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 74.2 |
TPSA ? Topological Polar Surface Area: Calculated from |
44.76 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.76 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.77 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.54 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.77 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.57 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.24 |
Solubility | 0.151 mg/ml ; 0.000576 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.36 |
Solubility | 0.116 mg/ml ; 0.000441 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.08 |
Solubility | 0.022 mg/ml ; 0.0000839 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) |
Yes |
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 |
-5.94 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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.86 |
* 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 potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In DMF (N,N-dimethyl-formamide); at 100℃; | Production Example 51 methyl 4-(6-bromoimidazo[1,2-a]pyridin-3-yl)benzoate 2.3 g methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate prepared according to T. Ishiyama et al., J. Org. Chem., 60, 7508 (1995), 2.0 g <strong>[474706-74-6]6-bromo-3-iodoimidazo[1,2-a]pyridine</strong> (compound in Production Example 49), 2. 5 g potassiumphosphate, 360 mg tetrakistriphenyl phosphine palladium and 30 ML N, N-dimethylformamide were heated at 100C under nitrogen atmosphere.. Insolubles were filtered off, the solvent was removed, and the residue was purified by NH silica gel column chromatography (hexane/ethyl acetate) and recrystallized from ethyl acetate to give 1.39 g of the title compound (colorless crystals).1H-NMR (CDCl3) delta: 3.97(s, 3H), 7.32(dd, J=9.6, 2.0Hz, 1H), 7.62(d, J=9.6Hz, 1H), 7.65(dt, J=8.8, 2.0Hz, 2H), 7.79(br.s, 1H), 8.21(dt, J=8.8, 2.0Hz, 2H), 8.50(br.s, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.7% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 100℃; for 24h;Inert atmosphere; | A mixture of 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c] pyrrole-1,4-dione (5) (1.97 g,2.90 mmol), methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (6) (0.76 g, 2.90 mmol), K2CO3 (1.60 g, 11.60 mmol),Pd(PPh3)4 (0.17 g, 5 mol%) and toluene/H2O (60 mL, 3/1, V/V) wasadded to the reaction flask under a N2 atmosphere and then stirred at100 C for 24 h. After cooling to the room temperature, the reactionmixture was extracted with CH2Cl2, washed with water and brine,and dried over MgSO4. The crude product was purified by columnchromatography (CH2Cl2/petroleum ether, 1/4, V/V) on silica gel toyield a purplish red solid (1.55 g, yield 72.7%). 1H NMR (400 MHz,CDCl3, delta/ppm): 8.97 (d, J = 4.2,1H), 8.11 (d, J = 8.5, 3H), 7.76 (d, J = 4.5,3H), 7.58 (d, J = 4.3, 1H), 4.11-4.04 (m, 3H), 3.96 (s, 4H), 1.93 (s, 2H),1.42-1.26 (m, 16H), 0.94-0.83 (m, 12H). MALDI-TOF MS (m/z): calcdfor (C76H75N3O4S3): 736.2004; Found: 736.2350. |
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