Structure of 27063-92-9
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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 27063-92-9 |
Formula : | C7H8BrN |
M.W : | 186.05 |
SMILES Code : | CC1=CC(C)=NC=C1Br |
MDL No. : | MFCD09842454 |
InChI Key : | SLMUXUHXAIPROA-UHFFFAOYSA-N |
Pubchem ID : | 13411100 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.29 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 41.87 |
TPSA ? Topological Polar Surface Area: Calculated from |
12.89 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.14 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.31 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.46 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.91 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.94 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.35 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.94 |
Solubility | 0.213 mg/ml ; 0.00114 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.22 |
Solubility | 1.12 mg/ml ; 0.00604 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.65 |
Solubility | 0.0415 mg/ml ; 0.000223 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) |
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 |
-5.79 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) |
1.41 |
* 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 |
---|---|---|
22%; 12%; 35% | Bromination of 2,4-lutidineTo 2,4-lutidine (5.39 mL, 46.7 mmol, 1 eq.) was added oleum (50 mL, containing 20percent free SO3) carefully under stirring at 0 0C. The reaction flask was fitted with a high-efficiency reflux condenser and heated to 165 °C in an oil bath. Bromine (4.3O mL, 83.4 mmol, 0.9 eq.) was added in portions of 0.5 mL over 5 h, and stirring was continued at 155-175 °C for 20 h. The solution was cooled to room temperature, poured on crushed ice (200 g) and stirred for 1 h. The resulting orange solution was neutralised by careful addition of solid Na2CO3, diluted with water and extracted with EtOAc (2 x 250 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by automated flash column chromatography (Biotage KP-Sil.(TM). SNAP 340 g cartridge, 0-15percent EtOAc/hexane) and dried in vacuo to furnish bromolutidines 8, 9 and 10.3,5-Dibromo-2,4-dimethylpyridine 8White solid (1.48 g, 12percent); mp 28-30 °C; 1H NMR deltaH (400 MHz; CDCl3) 2.54 (s, 3H, CH3), 2.61 (s, 3Eta, CH3), 8.41 (s, 1Eta, pyHortho); 13C NMR deltac (100 MHz; CDCl3) 23.8 (CH3), 25.7 (CH3), 120.3 (ArQ, 124.4 (ArQ, 146.4 (ArQ, 148.5 (ArCH), 156.5 (ArQ; IR vmax (filmVcm"1 3045, 2998, 2956, 2921, 1558, 1433, 1376, 1349, 1232, 1049, 993, 928, 783; HRMS (ESI+) for C7H8Br2N requires 263.9018, found (M+H+) 263.9027;5-Bromo-2,4-dimethylpyridine 9Colourless oil (1.89 g, 22percent); 1K NMR deltaH (400 MHz; CDCl3) 2.32 (s, 3H, CH3), 2.44 (s, 3Eta, CH3), 7.00 (s, 1Eta, pyHortho), 8.47 (s, 1Eta, pyHmeta); 13C NMR deltac (100 MHz; CDCl3) 22.1 (CH3), 23.6 (CH3), 120.4 (ArQ, 125.5 (ArCH), 146.7 (ArQ, 150.5 (ArCH), 157.0 (ArQ; IR vmax (filmycm"1 2985, 2957, 2924, 2854, 1592, 1461, 1377, 1353, 1289, 1177, 1032; HRMS (ESI+) for C7H9BrN requires 185.9913, found (M+H+) 185.9918;3-Bromo-2,4-dimethyIpyridine 10Colourless oil (3.04 g, 35percent); 1U NMR deltaH (400 MHz; CDCl3) 2.33 (s, 3H, CH3), 2.61 (s, 3Eta, CH3), 6.91 (d, J=5.0 Hz, IH, pyHmeta), 8.18 (d, J=5.0 Hz, IH, pyHortho); 13C NMR deltac (100 MHz; CDCl3) 23.2 (CH3), 25.7 (CH3), 123.4 (ArCH), 124.3 (ArQ, 146.7 (ArCH), 147.3 (ArQ, 157.4 (ArQ; IR vmax (filn^/cm-1 3050, 2995, 2958, 2922, 1585, 1437, 1389, 1123, 1024, 916, 825; HRMS (ESI+) for C7H9BrN requires 185.9913, found (M+H+) 185.9917; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; | Example 1 Preparation of 5-bromo-2,4-dimethylpyridine STR13 150 ml of 65percent strength oleum are added dropwise to 28.9 ml of 2,4-dimethylpyridine, while cooling with ice and stirring, such that the temperature does not rise above 35° C. When the solution has become homogeneous, 6.42 ml of bromine are slowly added dropwise, with stirring. The mixture is stirred at 80° C. for 31/2 hours. After cooling, it is carefully added dropwise to 1 kg of ice, neutralized with solid Na2 CO3 and extracted 3 times with 300 ml of ether each time. The organic layer is separated off and dried over magnesium sulfate. After removal of the solvent by distillation in vacuo, 34.6 g of a pale yellow oil consisting of the isomers 5-bromo-2,4-dimethylpyridine and 3-bromo-2,4-dimethylpyridine are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The isomers are separated by column chromatography on silicon dioxide gel to give 10 g of 5-bromo-2,4-dimethylpyridine as a colorless liquid (13.0 g of <strong>[27063-93-0]3-bromo-2,4-dimethylpyridine</strong>). Yield: 22percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; | (a) Oleum (65percent, 600 ml) was carefully added to cold 2,4-dimethylpyridine (107.4 g). Bromine (80 g) was added and the mixture was heated for 20 hours at 55°, allowed to cool and poured on to ice. The mixture was neutralised with aqueous sodium hydroxide and extracted with ether. The ether extracts were stirred with ferrous sulphate overnight, evaporated and the residue was distilled to give a mixture of 3-bromo-2,4-dimethylpyridine and 5-bromo-2,4-dimethylpyridine (66.6 g, b.p. 88°-90° at 11 mm Hg). |