Structure of 914950-66-6
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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. : | 914950-66-6 |
Formula : | C9H7NO2 |
M.W : | 161.16 |
SMILES Code : | COC(=O)C1=NC(=CC=C1)C#C |
MDL No. : | MFCD18207403 |
InChI Key : | ZUYYFZHPZOLVKD-UHFFFAOYSA-N |
Pubchem ID : | 22125909 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.11 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 43.45 |
TPSA ? Topological Polar Surface Area: Calculated from |
39.19 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.96 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.32 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.93 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.89 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.81 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.38 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.91 |
Solubility | 1.99 mg/ml ; 0.0123 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.74 |
Solubility | 2.91 mg/ml ; 0.018 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.17 |
Solubility | 1.08 mg/ml ; 0.00671 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 |
-6.35 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) |
2.05 |
* 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 |
---|---|---|
(b) Methyl 6-ethynylpyridine-2-carboxylate: In a similar manner to that of Example 57(b), starting with 2.25 g (9.6 mmol) of the compound obtained in Example 60(a), 380 mg (24%) of the expected compound are obtained in the form of a yellow powder with a melting point of 40-45 C. 1 H NMR (CDCl3) delta 3.40 (s, 1H), 4.02 (s, 3H), 7.93 (dd, 1H, J=8.1/2.0 Hz), 8.12 (d, 1H, J=8.1 Hz), 8.83 (d, 1H, J=1.9 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium fluoride; In methanol; dichloromethane; at 20.0℃; for 12.0h; | To a solution of methyl 6-((trimethylsilyl)ethynyl)picolinate 52(1.0 g, 4.23 mmol) in a mixture of CH2Cl2/MeOH (26 mL, 50:50, v/v)was added KF (0.74 g, 12.7 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (petroleum ether/EtOAc, 80/20) to afford 54(562 mg) as a brown solid in 82% yield. 1H NMR (300 MHz, CDCl3)delta 8.06 (dd, J 7.8, 0.9 Hz, 1H), 7.80 (t, J 7.8 Hz, 1H), 7.61 (dd, J 7.8,1.0 Hz, 1H), 3.97 (s, 3H), 3.18 (s, 1H). 13C NMR (75 MHz, CDCl3)delta 165.2, 148.5, 142.6, 137.4, 130.6, 124.7, 82.0, 78.6, 53.1. MS (ESI):m/z (%): 162 (100) [MH]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In water; tert-butyl alcohol; at 20.0℃; for 24.0h; | General procedure: The alkyne (6 or 7, 1.24 mmol) was dissolved in tert-butanol(10 mL) and added to a water solution (10 ml) of N,N-Dimethyl-N-(3-azidopropyl)amine hydrochloride(226 mg, 1.37 mmol), copper (II) sulphate pentahydrate (31 mg, 10% mol) and sodium ascorbate (246 mg,1.24 mmol). The resulting mixture was stirred for 24 h, at r.t. The organic solvent was removed undervacuum and the residue was diluted with saturated NaHCO3 (10 mL) and extracted with DCM(3 x 20 mL). The combined organic phases were dried over Na2SO4 and the solvent was removedunder reduced pressure. The crude was purified by flash chromatography (CHCl3/MeOH 95:5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrazine hydrate; In methanol; at 20.0℃; for 0.75h; | General procedure: To a stirred solution of methyl ester (1.0 equiv) in MeOH (0.3 Ml)was added hydrazine monohydrate (7.0 equiv). After 45 min, the mixture was concentrated under reduced pressure without further purification. |
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