Structure of 475102-10-4
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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. : | 475102-10-4 |
Formula : | C14H14N2O2 |
M.W : | 242.27 |
SMILES Code : | O=C(N1C=CC2=C1C=CC(C#N)=C2)OC(C)(C)C |
MDL No. : | MFCD08056374 |
InChI Key : | OYPSWAHXXPMBGM-UHFFFAOYSA-N |
Pubchem ID : | 7213332 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 18 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.29 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 68.86 |
TPSA ? Topological Polar Surface Area: Calculated from |
55.02 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.89 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.99 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.3 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.96 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.09 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.64 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.4 |
Solubility | 0.0969 mg/ml ; 0.0004 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.81 |
Solubility | 0.0376 mg/ml ; 0.000155 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.45 |
Solubility | 0.086 mg/ml ; 0.000355 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) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
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 |
-5.65 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 |
0.0 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) |
2.12 |
* 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 |
---|---|---|
96% | Stage #1: With dmap In tetrahydrofuran at 20℃; for 0.5 h; Stage #2: for 2 h; |
In a 100 mL round-bottom flask was placed 1H-INDOLE-5-CARBONITRILE (2.0 g, 14.07 MMOL) in 20 mL of anhydrous THF. To this solution was added DMAP (0.86 g, 7.03 MMOL) and the mixture was allowed to stir for 0.5 h at rt. At this point, BOC20 (3.07 g, 14.07 MMOL) was added and the reaction stirred for an additional 2 h. The reaction was then quenched with water and extracted twice with ethyl ether. The combined organic layers were washed successively with 1 N HCI, water, and brine, then dried over MGS04 and concentrated to provide 3.26 g (96percent) of the desired product as a white SOLID.APOS;H- NMR (DMSO-d6) 8 8.20-8. 14 (m, 2H), 7.83 (d, 1H), 7.70 (d, 1H), 6.80 (d, 1H), 1.63 (s, 9H). |
96% | Stage #1: With dmap In tetrahydrofuran at 20℃; for 0.5 h; Stage #2: for 2 h; |
In a 100 ml round-bottom flask was placed 1W-indole-5-carbonitrile (2.0 g, 14.07mmol) in 20 ml of anhydrous THF. To this solution was added DMAP (0.86 g, 7.03mmol) and the mixture was allowed to stir for 0.5 h at rt. At this point, BocaO (3.07 g,14.07 mmol) was added and the reaction stirred for an additional 2 h. The reaction wasthen quenched with water and extracted twice with ethyl ether. The combined organiclayers were washed successively with 1N HCI, water, and brine, then dried over MgSO4and concentrated to provide 3.26 g (96percent) of the desired product as a white solid. 1H-NMR (DMSO-c/e) 5 8.20-8.14 (m, 2H), 7.83 (d, 1H), 7.70 (d, 1H), 6.80 (d, 1H), 1.63 (s,9H). |
90% | With dmap In acetonitrile at 20℃; for 0.5 h; | [0486] tert-butyl 5-cyano-l H-indole-1 -carboxylate (INT-65) [0487] To a flask containing 5-cyanoindole (500 mg, 3.52 mmol) in CH3CN (5 mL) was added Boc20 (920 mg, 4.22 mmol) and DMAP (42 mg, 0.35 mmol) and the mixture was stirred at room temperature for 0.5 h. The mixture was concentrated, redissolved in DCM and chromatographed (EtOAc / hexanes) to provide 766 mg (90percent) of tert-butyl 5-cyano-lH- indole-l-carboxylate INT -65 as a white solid. LCMS-ESI (m/z) calculated for C14H14N20 :242.27; found 243.1 [M+H]+, tR = 3.93 min. |
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