Structure of 7697-28-1
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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. : | 7697-28-1 |
Formula : | C8H7BrO2 |
M.W : | 215.04 |
SMILES Code : | O=C(O)C1=CC=C(Br)C(C)=C1 |
MDL No. : | MFCD00039526 |
InChI Key : | KWVXDZLVCISXIB-UHFFFAOYSA-N |
Pubchem ID : | 82131 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 46.07 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.64 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.74 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.46 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.67 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.35 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.37 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.24 |
Solubility | 0.125 mg/ml ; 0.000579 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.18 |
Solubility | 0.143 mg/ml ; 0.000664 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.02 |
Solubility | 0.207 mg/ml ; 0.000962 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) |
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 |
-5.67 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 |
0.56 |
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) |
1.29 |
* 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 |
---|---|---|
8.9g (89%) | In N-methyl-acetamide; methanol; dichloromethane; water; | EXAMPLE 21 N- (3, 4-Dimethyl-5-isoxazolyl) -2'-›(formylamino)[methyl]-4'-(2-oxazolyl)›1,1'-[biphenyl]-2-sulfonamide STR48 A. 4-Bromo-3-methylbenzamide To a solution of 10 g (46.5 mmol) of 4-bromo-3-methyl benzoic acid in 200 mL of dichloromethane under argon, 30 mL of 2M solution of oxalyl chloride in dichloromethane w as added. Four drops of dimethylformamide was then added and the mixture was stirred at room temperature for 1 hour. The soltion was evaporated and dried in vacuo. The residue was dissolved in 100 mL of methanol, and 25 mL of 28% aqueous ammonium hydroxide was added to the mixture. The solution was stirred at room temperature for 3 hours, and then diluted with 500 mL of water. The resulting white solid was filtered, washed with water and dried to afford 8.9g (89%) of compound A. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With disodium hydrogenphosphate; disodium bis(2-aminopyrimidine-4,6-diolate)palladium acetate; In water; at 50 - 120℃; for 0.166667h;Microwave irradiation; | In a 35 mL microwave reaction vessel, commercially available 4-bromo-3- methylbenzoic acid (0.2 g, 0.93 mmol), o-tolylboronic acid (0.151 g, 1.12 mmol) and Na2HPO4 (0.66 g, 4.65 mmol) were sequentially added. H20 (6.0 mL) was added and the mixture stirred at 50 C to dissolve most of the materials. Bis-(disodium 2-aminopyrimidine-4,6-diolate) palladium acetate [prepared as described in I Am. Chem. Soc. 2009, 131, 16346-1 6347] (0.01 M in Pd(II),1.50 mL, 0.0 15 mmol) was added to the reaction and the tube was heated to 120 C under microwave irradiation for 10 mm, under vigorous stirring. After cooling to r.t., the reaction was partitioned between 1.0 M HC1 solution (100 mL) and EtOAc (100 mL). The organic layer was separated, dried over Na2504, filtered and concentrated affording a solid residue (0.304 g). Purification by typical silica gel flash chromatography (CH2C12) afforded the pure titlecompound (0. 20 g, 95%) as a white wax. R= 2.20 mm. MS (ESI) m/z: 225 [M-Hf. ?H NMR (DMSO-d6): oe 12.90 (s, 1H), 7.90 (d, 1H, J= 1.0 hz), 7.80 (dd, 1H, J= 7.9, 1.6 Hz), 7.35-7.23 (m, 3H), 7.19 (d, 1H, J= 7.9 Hz), 7.07 (dd, 1H, J= 7.5, 1.4 Hz), 2.04 (s, 3H), 1.99 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.27 g | With potassium carbonate; In N,N-dimethyl-formamide; at 95℃; for 2h;Inert atmosphere; | A mixture of crude 3-(methylsulfonyl)propyl-p-toluenesulfonate 24b (1.87 g, 6.42 mmol), 4-bromo-3-methylbenzoic acid (1.0 g, 5.34 mmol) and potassium carbonate (1.47g, 10.68 mmol) was dissolved in 20 mL of N, N-dimethylformamide, heated to 95 C and stirred for 2 hours. The aqueous phase was extracted with ethyl acetate (30 mL of X2) and the organic phases were combined, washed sequentially with water (30 mL of X3), saturated sodium chloride solution (30 mL), and the mixture was extracted with ethyl acetate (50 mL) and stirred for 30 min. Dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using eluent system B to give the title product bromo-2-methyl-4-(3-(methylsulfonyl)propoxy)benzene 24c (1.27 g, yellow solid), yield: 77.4%. |
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