Structure of 102562-86-7
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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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CAS No. : | 102562-86-7 |
Formula : | C8H10N2O |
M.W : | 150.18 |
SMILES Code : | NCC1=CC=CC(=C1)C(N)=O |
MDL No. : | MFCD07186292 |
InChI Key : | HYHLWVJLJXARGY-UHFFFAOYSA-N |
Pubchem ID : | 10103327 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P301+P312+P330 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 42.21 |
TPSA ? Topological Polar Surface Area: Calculated from |
69.11 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.91 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-4.76 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.09 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.65 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.58 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.51 |
Log S (ESOL):? ESOL: Topological method implemented from |
1.96 |
Solubility | 13600.0 mg/ml ; 90.4 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (Ali)? Ali: Topological method implemented from |
3.94 |
Solubility | 1300000.0 mg/ml ; 8650.0 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.01 |
Solubility | 1.45 mg/ml ; 0.00968 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 |
No |
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 |
-10.6 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 |
2.0 |
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) |
1.0 |
* 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 |
---|---|---|
The reaction was pressurised to 60 psi at room temperature with hydrogen, and stirred for 18 hours. Starting material remained, so a further aliquot of 10% palladium on carbon (500 mg) was added and the procedure was repeated. The reaction mixture was filtered through arbocel washing with acetic acid and the filtrate was concentrated under reduced pressure. The residue was azeotroped with toluene and purified by flash chromatography on silica gel eluding with dichloromethane:methanol:0.88 ammonia (100:0:0 changing to 90:10:1 then 85:15:1.5, by volume) to provide the title compound (5.3 g) as a colourless oil. 1H NMR (400 MHz, CD3OD): delta=3.83 (s, 2H), 7.39 (dd, 1H), 7.49 (d, 1H), 7.73 (d, 1H), 7.81 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 14h; | To a solution of Intermediate 1h (50 mg, 0.152 mmol) and <strong>[102562-86-7]3-aminomethyl-benzamide</strong> (60 mg, 0.228 mmol) in 2 mL DMF, were added iPr2Net (106 muL, 0.608 mmol), HOAT (41.4 mg, 0.304 mmol) and EDCI (35 mg, 0.182 mmol). The mixture was stirred at rt for 14 h, then was diluted with EtOAc. The organic phase was washed with H2O, 1N HCl, H2O, 0.1 N, NaOH, and brine, dried (Na2SO4), and concentrated. The crude product was recrystallized from methanol to afford 7.2 mg (10%) of Example 24. MS (HR-ESI) calculated for C24H24N5O5 (M+H+), found 462.1787; MS (ESI) 462.3 (M+H+), 484.3 (M+Na+); 1H NMR (300 MHz, CD3OD) delta. 8.51 (br. S, 1H), 7.84 (s, 1H), 7.78 (d, J=7.7, 1H), 7.53-7.31 (m, 7H), 5.20 (s, 2H), 5.13 (dd, J=3.0, 1.0, 1H), 4.61-4.37 (m, 2H), 3.25-3.16 (m, 1H), 3.12-3.03 (m, 1H), 2.66-2.55 (m, 1H), 2.32-2.24 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dimethyl sulfoxide; at 60℃; for 12h; | Step l 5 A bromoacetal resin (37mg, 0.98 mmol/g) and a solution of <strong>[102562-86-7]3-(aminomethyl)benzamide</strong> in DMSO (1.4 mL) were placed in a Robbins block (FlexChem) having 96 well plates. The reaction mixture was shaken at 60C using a rotating oven [Robbins Scientific] for 12 hours. The resin was washed with DMF, MeOH, and then DCM |
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