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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
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Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Structure of 5239-82-7
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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.
4.5
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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'.
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'.
Search for reports by entering the product batch number.
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CAS No. : | 5239-82-7 |
Formula : | C5H8O2 |
M.W : | 100.12 |
SMILES Code : | O=C(O)CC1CC1 |
MDL No. : | MFCD00041544 |
InChI Key : | KVVDRQDTODKIJD-UHFFFAOYSA-N |
Pubchem ID : | 138440 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H315-H318-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Class: | 8 |
UN#: | 3265 |
Packing Group: | Ⅱ |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.8 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 25.81 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.09 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.84 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.81 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.5 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.74 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.8 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.86 |
Solubility | 13.9 mg/ml ; 0.139 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.21 |
Solubility | 6.23 mg/ml ; 0.0622 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.18 |
Solubility | 66.3 mg/ml ; 0.662 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 |
-6.31 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 |
1.0 |
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) |
1.0 |
* 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 |
---|---|---|
70% | Step 1. ethyl bromo(cyclopropyl)acetate Thionyl chloride (0.46 mL, 6.3 mmol) was added dropwise to a solution of cyclopropylacetic acid (0.5 g, 5 mmol) (Oakwood cat003710) in 1,2-dichloroethane (5.2 mL) at room temperature. The reaction was heated to reflux for 2 h then allowed to cool to room temperature, at which time N-bromosuccinimide (1.12 g, 6.27 mmol) and hydrogen bromide (2 mu, 0.04 mmol) (48% aqueous solution) were added successively. The resulting mixture was heated to reflux for 2 days. The reaction mixture was then cooled to room temperature, ethanol (4 mL) was added, and the reaction was stirred at room temperature for an additional 2 h. The reaction mixture was then concentrated to afford the crude product. The crude product was dissolved in carbon tetrachloride and was passed through a short column of silica gel and concentrated to afford ethyl bromo(cyclopropyl)acetate (0.70 g, 70%) as an oil. | |
Racemic ethyl 2-bromo-2-cyclopropylacetate The above compound was prepared by adding a solution of 2-cyclopropylacetic acid (24.7 g, 247 mmol) in anhydrous DCE (250 mL) to thionyl chloride (22 mL, 302 mmol) dropwise over 5 minutes at 25 C. After refluxing for 2 hours, the reaction was cooled to room temperature, and N-bromosuccinimde (53.6 g, 301 mmol) and hydrogen bromide (48% aqueous solution; 0.195 mL, 1.727 mmol) were added successively at 25 C. The mixture was refluxed for 3 days, then cooled to room temperature. Absolute EtOH (200 mL) was added and the resulting dark brown solution was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure and the residue was suspended in carbon tetrachloride (300 mL) and filtered through a glass filter. The filtrate was concentrated under the reduced pressure. The crude product was purified by flash chromatography (silica-gel, 330 g x 2, 5 % ethyl acetate in hexanes) to provide ethyl 2-bromo-2-cyclopropylacetate. .H NMR (400 MHz, CDCk) delta ppm 4.24 (m, 2 H), 3.58 (d, J=12.0 Hz, 1H), 1.58 (m, 1H), 0.90-0.80 (m, 2 H), 0.53 (m, 1H), 0.42 (m, 1H), 1.3 (t, J = 8.0 Hz, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
165 mg | Example 15 1- (2- (Cyclopropylmethyl) -l-methyl-lH-benzimidazol-6-yl) -4- ( (4- fluorobenzyl) oxy) pyridin-2 ( 1H) -one A) 6-Bromo-2- (cyclopropylmethyl) -1-methyl-lH-benzimidazole Zinc (212 mg) was added to a mixture of 5-bromo-N-methyl- 2-nitroanilin.e (150 mg) , NH4C1 (347 mg) , eOH (2 ml) and water (1 ml) at room temperature. The mixture was stirred at room temperature for 1 h. After filtration and addition of saturated NaHC03 solution, the mixture was concentrated and extracted with AcOEt . The organic layer was separated, washed with brine, dried over MgS04 and concentrated in vacuo. To the resulting residue, DMF (2.0 ml), cyclopropylacetic acid (0.060 ml), N,N-diisopropylethylamine (0.339 ml) and HATU (259 mg) were added, and the mixture was stirred at room temperature for 1 h. The mixture was. quenched with brine and extracted with EtOAc twice. The organic layer was separated, washed with brine, dried over MgS04, passed through NH silica pad and concentrated in vacuo. The resulting residue was dissolved in AcOH (2.0 ml), and stirred at 80C for i h. After evaporation of the solvent, the residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (165 mg). as a purple gum. MS (ESI+) : [M+H] + 265.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | General procedure: HATU (4.89 g, 12.9 mmol) was added to a solution of the intermediate 4-bromo-N2-ethylbenzene-1,2-diamine, DIPEA (6.40 mL, 36.7 mmol), and cyclopropanecarboxylic acid (0.98 mL, 12.2 mmol) in DMF (40 mL), and the mixture was stirred at rt for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was dissolved in AcOH (40 mL) and the mixture was stirred at 80 C for 1 h. After concentration of the mixture, the residue was neutralized with satd NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, hexane/EtOAc = 100/0 to 0/100) to give the title compound (1.2 g, 37%) as a pale yellow solid. |