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Structure of 2,6-Dichloro benzyl chloride
CAS No.: 2014-83-7
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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. : | 2014-83-7 |
Formula : | C7H5Cl3 |
M.W : | 195.47 |
SMILES Code : | ClCC1=C(Cl)C=CC=C1Cl |
MDL No. : | MFCD00000897 |
InChI Key : | LBOBESSDSGODDD-UHFFFAOYSA-N |
Pubchem ID : | 74832 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅱ |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 46.22 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.31 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.29 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.58 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.1 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.08 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.47 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.5 |
Solubility | 0.0614 mg/ml ; 0.000314 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.97 |
Solubility | 0.212 mg/ml ; 0.00108 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.65 |
Solubility | 0.00434 mg/ml ; 0.0000222 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
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) |
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 |
-5.16 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 |
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) |
1.37 |
* 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 |
---|---|---|
10.4 g | With potassium carbonate; In N,N-dimethyl-formamide; at 1 - 40℃; for 20h; | (1) Synthesis of 6-bromo-1-(2,6-dichlorobenzyl)-3-methyl-1H-indazole [1-1] (hereinafter referred to as a compound [1-1]) To a solution of <strong>[7746-27-2]6-bromo-3-methyl-1H-indazole</strong> (9.57 g), which was obtained by the method described in the document (JP 2009-528363 W), in N,N-dimethylformamide (100 mL), were added potassium carbonate (12.6 g) and 2,6-dichlorobenzyl chloride (9.79 g) and the mixture was stirred at room temperature for 20 hours. The reaction mixture was quenched with water, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (10.4 g) as a white solid. 1H-NMR (400 MHz, CDCl3) delta: 7.55 (1H, s), 7.47 (1H, d, J = 8.5 Hz), 7.38 (2H, d, J = 8.1 Hz), 7.25 (1H, d, J = 5.9 Hz), 7.22-7.20 (1H, m), 5.66 (2H, s), 2.50 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5% | In N,N-dimethyl-formamide; at 85.0℃; | A mixture of <strong>[22387-37-7]8-methyl-9H-purin-6-ylamine</strong> (150 mg, 1.0 mmol) and l,3-dichloro-2- chloromethyl-benzene (214 mg, 1.1 mmol) in DMF (3 mL) was stirred at 85 C overnight. The mixture was cooled and filtered. The filtrate was purified by prep-HPLC (NH4HCO3 system) to give 3-(2,6-dichloro-benzyl)-8-methyl-3H-purin-6-ylamine (2 mg, yield: 5 %) as white solid. 1H NMR (400 MHz, DMSO- d): d = 7.82 (s, 1H), 7.70 (brs, 2H), 7.60-7.58 (m, 2H), 7.51-7.47 (m, 1H), 5.67 (s, 2H), 2.38 (s, 3H). MS: m/z 308.0 (M+H+). |
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