Structure of 81477-94-3
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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. : | 81477-94-3 |
Formula : | C19H21NO2 |
M.W : | 295.38 |
SMILES Code : | O=C(OC(C)(C)C)C/N=C(C1=CC=CC=C1)\C2=CC=CC=C2 |
MDL No. : | MFCD00134280 |
InChI Key : | YSHDPXQDVKNPKA-UHFFFAOYSA-N |
Pubchem ID : | 688171 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 22 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.26 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 89.74 |
TPSA ? Topological Polar Surface Area: Calculated from |
38.66 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.4 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.45 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.87 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.41 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.7 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.96 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.48 |
Solubility | 0.00973 mg/ml ; 0.0000329 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.98 |
Solubility | 0.00309 mg/ml ; 0.0000105 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-6.3 |
Solubility | 0.000147 mg/ml ; 0.000000498 mol/l |
Class? Solubility class: Log S scale |
Poorly 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) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
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 |
-4.94 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.0 |
* 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 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; (2S,4S,5R)-1-(anthracen-9-ylmethyl)-5-ethenyl-2-[(R)-(prop-2-en-1-yloxy)(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium bromide; In dichloromethane; at -78 - 20℃; | This, together with tert-butyl 2- (diphenylmethyleneamino)acetate (4.71 g) and (2S,4S,5R)-2-((R)-allyloxy(quinolin-4- yl)methyl)-l-(anthracen-9-ylmethyl)-5-vinyl-l-azoniabicyclo[2.2.2]octane bromide (1.073 g)5 was dissolved in DCM (100 mL) and the solution was cooled to -78 0C under nitrogen. 2-tert- Butylimino-2-diethylamino-l,3-dimethyl-perhydro-l,3,2-diazaphosphorine (5 mL) was added drop wise over 5 min and the mixture was stirred at -78 0C for 7 h then allowed to reach RT overnight. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and water. The ethyl acetate was washed with brine, dried over magnesium sulfate, io filtered and concentrated in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With C37H37N2O(1+)*Br(1-); potassium hydroxide; In chloroform; water; toluene; at -40℃; for 72h; | A 10 mL reactiontube was charged with 2 (30 mg, 0.1 mmol), 3,5-dichlorobenzyl bromide (119 mg, 0.5 mmol, 5 equivalent), catalyst 1f (6 mg, 0.01 mmol, 0.1 equivalent) and toluene and CHCl3 (1.5 mL, 2:1 v/v),and the mixture was cooled to 40 C. After the mixture was stirred for 10 min, 50% aq. KOH (28L, 0.1 mmol, 5 equivalent) was added, and the whole reaction mixture was stirred at 40 C for72 h before being allowed to warm to ambient temperature. The reaction was quenched by addingH2O (2 mL), and the resulting mixture was extracted with EtOAc (3 10 mL). The combined extractswere washed with brine (10 mL) and dried (anhydrous Na2SO4), and the crude product was purifiedby flash column chromatography (eluting with hexane/EtOAc, 50:1) to afford 4a (43 mg, 95% yield)as light yellow liquid. 97% ee; []20D 178.8 (c = 1.0, CH2Cl2); 1H-NMR (400 MHz, CDCl3): 7.57 (s,1H), 7.55 (d, J = 1.4 Hz, 1H), 7.40-7.29 (m, 6H), 7.16 (t, J = 1.7 Hz, 1H), 6.95 (d, J = 1.7 Hz, 2H), 6.76(d, J = 6.1 Hz, 2H), 4.12 (dd, J = 8.9, 4.6 Hz, 1H), 3.19-3.08 (m, 2H), 1.45 (s, 9H); 13C-NMR (100 MHz,CDCl3): 171.1, 170.2, 141.7, 139.2, 136.1, 134.4, 130.3, 128.7, 128.6, 128.3, 128.3, 128.0, 127.6, 126.4, 81.6,66.9, 38.9, 28.0; HRMS (ESI, positive): Calcd. for C26H26Cl2NO2 [M + H]+ 454.1335, found: 454.1333.HPLC analysis: Daicel Chiralcel OD-H, n-hexane/isopropanol = 95:5, flow rate = 0.5 mL/min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With C37H37N2O(1+)*Br(1-); potassium hydroxide; In chloroform; water; toluene; at -40℃; for 72h; | A 10 mL reactiontube was charged with 2 (30 mg, 0.1 mmol), 3,5-dichlorobenzyl bromide (119 mg, 0.5 mmol, 5 equivalent), catalyst 1f (6 mg, 0.01 mmol, 0.1 equivalent) and toluene and CHCl3 (1.5 mL, 2:1 v/v),and the mixture was cooled to 40 C. After the mixture was stirred for 10 min, 50% aq. KOH (28L, 0.1 mmol, 5 equivalent) was added, and the whole reaction mixture was stirred at 40 C for72 h before being allowed to warm to ambient temperature. The reaction was quenched by addingH2O (2 mL), and the resulting mixture was extracted with EtOAc (3 10 mL). The combined extractswere washed with brine (10 mL) and dried (anhydrous Na2SO4), and the crude product was purifiedby flash column chromatography (eluting with hexane/EtOAc, 50:1) to afford 4a (43 mg, 95% yield)as light yellow liquid. 97% ee; []20D 178.8 (c = 1.0, CH2Cl2); 1H-NMR (400 MHz, CDCl3): 7.57 (s,1H), 7.55 (d, J = 1.4 Hz, 1H), 7.40-7.29 (m, 6H), 7.16 (t, J = 1.7 Hz, 1H), 6.95 (d, J = 1.7 Hz, 2H), 6.76(d, J = 6.1 Hz, 2H), 4.12 (dd, J = 8.9, 4.6 Hz, 1H), 3.19-3.08 (m, 2H), 1.45 (s, 9H); 13C-NMR (100 MHz,CDCl3): 171.1, 170.2, 141.7, 139.2, 136.1, 134.4, 130.3, 128.7, 128.6, 128.3, 128.3, 128.0, 127.6, 126.4, 81.6,66.9, 38.9, 28.0; HRMS (ESI, positive): Calcd. for C26H26Cl2NO2 [M + H]+ 454.1335, found: 454.1333.HPLC analysis: Daicel Chiralcel OD-H, n-hexane/isopropanol = 95:5, flow rate = 0.5 mL/min. |