Structure of 62882-02-4
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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.
4.5
*For Research Use Only! Not for Human Use. We Do Not Sell to Patients.
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| CAS No. : | 62882-02-4 |
| Formula : | C9H6ClN |
| M.W : | 163.60 |
| SMILES Code : | ClC1=CC2=C(C=NC=C2)C=C1 |
| English Name : | 6-Chloroisoquinoline |
| MDL No. : | MFCD09991646 |
| InChI Key : | NCJNOOHAQSFEJN-UHFFFAOYSA-N |
| Pubchem ID : | 12371746 |
| Num. heavy atoms | 11 |
| Num. arom. heavy atoms | 10 |
| Fraction Csp3 | 0.0 |
| Num. rotatable bonds | 0 |
| Num. H-bond acceptors | 1.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 46.75 |
| TPSA ? Topological Polar Surface Area: Calculated from |
12.89 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.94 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.88 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.89 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.15 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.13 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.6 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-3.34 |
| Solubility | 0.0745 mg/ml ; 0.000456 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-2.81 |
| Solubility | 0.253 mg/ml ; 0.00155 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.31 |
| Solubility | 0.00807 mg/ml ; 0.0000493 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) |
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) |
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 |
-5.25 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) |
1.15 |
* 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 |
|---|---|---|
| 64% | Stage #1: 6-chloro-1H-indene With ozone In methanol; dichloromethane at -78℃; Stage #2: With dimethylsulfide; sodium hydrogencarbonate In methanol; dichloromethane for 6h; Stage #3: With ammonium hydroxide In methanol; dichloromethane for 15h; Further stages.; | |
| Multi-step reaction with 2 steps 1.1: ozone; oxygen / methanol; dichloromethane / 0.5 h / -78 - -65 °C / Inert atmosphere 1.2: 16 h / 20 °C / Inert atmosphere 2.1: ammonium hydroxide / dichloromethane; methanol / 24 h / 20 °C | ||
| 37 % | With [bis(acetoxy)iodo]benzene; ammonium carbamate In methanol at 0 - 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 46% | With N-ethyl-N,N-diisopropylamine In toluene at 45℃; for 1h; Inert atmosphere; | 3-[2-(N,N-Dimethylsulfamoyl)-1,2-dihydroisoquinolin-1-yl]-1H-indol-7-yl Acetate (37a) General procedure: Dimethylsulfamoyl chloride (34; 0.144 mL, 1.34 mmol) was added to a solution of isoquinoline (5; 157 mg, 1.22 mmol) and 1H-indol-7-yl acetate (33; 213 mg, 1.22 mmol) in toluene (4 mL) at r.t. The mixture was concentrated to a thick but stirrable paste (1.5 mL), which was stirred at 50 °C for 3 h. TLC and LCMS showed reaction was largely complete by this time. The mixture was diluted with EtOAc (40 mL), washed with H2O (40 mL) and sat. brine (20 mL), dried (Na2SO4), filtered and evaporated to dryness. The residue was purified by flash silica gel chromatography (loading in CH2Cl2) (eluent: gradient 20 to 50% EtOAc in heptane). Fractions containing the desired product were evaporated to afford the title compound 37a (208 mg, 42%) as a white solid |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / toluene / 1.5 h / 120 °C / Dean-Stark 2.1: ozone; oxygen / methanol; dichloromethane / 0.5 h / -78 - -65 °C / Inert atmosphere 2.2: 16 h / 20 °C / Inert atmosphere 3.1: ammonium hydroxide / dichloromethane; methanol / 24 h / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 73 % | With nickel(II) iodide; trimethylsilyl bromide; tris-(trimethylsilyl)silane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 50℃; Inert atmosphere; Irradiation; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 4 steps 1: potassium <i>tert</i>-butylate / tert-butyl methyl ether / 16 h / 55 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 5 - 20 °C 3: methanesulfonyl chloride / water; tetrahydrofuran / 2.5 h / 20 °C 4: acetyl chloride / isopropyl alcohol / 1450 min / 0 - 25 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 64% | Stage #1: 6-chloroisoquinoline With di-<i>tert</i>-butyl dicarbonate In tetrahydrofuran at 50℃; Stage #2: With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 2h; Stage #3: With hydrogenchloride at 20℃; for 6h; | |
| Multi-step reaction with 2 steps 1: acetone / 24 h / 60 °C 2: N-Bromosuccinimide; potassium dihydrogenphosphate / 1,2-dichloro-ethane / 16 h / 100 °C / Schlenk technique |