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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+ |
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Structure of 877-88-3
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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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CAS No. : | 877-88-3 |
Formula : | C9H11BrO2 |
M.W : | 231.09 |
SMILES Code : | COC1=CC(OC)=CC(CBr)=C1 |
MDL No. : | MFCD01321368 |
InChI Key : | BTHIGJGJAPYFSJ-UHFFFAOYSA-N |
Pubchem ID : | 1274490 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅱ |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 52.26 |
TPSA ? Topological Polar Surface Area: Calculated from |
18.46 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.63 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.42 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.45 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.25 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.83 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.52 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.97 |
Solubility | 0.248 mg/ml ; 0.00107 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.45 |
Solubility | 0.82 mg/ml ; 0.00355 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.92 |
Solubility | 0.028 mg/ml ; 0.000121 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 |
-5.99 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 |
0.55 |
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) |
1.73 |
* 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 |
---|---|---|
14% | With potassium carbonate; In acetone; at 20℃; | General procedure: A mixture of 44 (300 mg, 1.56 mmol), K2CO3 (372 mg, 2.34 mmol), and halogenated compound (1 equiv) in acetone (10 mL) was stirred for 0.5-3.5 h at rt. After filtering the mixture and removing the solvent in vacuo, the residue was purified by column chromatography (eluent: hexane/EtOAc 85:15) to obtain the target compounds (11-23) as white solids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1h; | Potassium carbonate (1.05g, 7.6 mmol) was slowly added to a stirred solution of 2- chloropyrimidin-5-ol (0.5g, 3.8 mmol) in DMF (5mL) followed by the addition of 3- (bromomethyl)-l,5-dimethoxybenzene (0.97g, 4.2 mmol) at 0 °C. The reaction mass was stirred at room temperature for lh then the reaction mixture was quenched with ice cold water. The solid that separated was filtered and dried under reduced pressure to afford desired title compound (0.9 83percent). LCMS: m/z = 281.2 (M+H)+. |
360 mg | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 7h;Cooling with ice; | Preparation Example 13 A mixture of <strong>[4983-28-2]2-chloro-5-hydroxypyrimidine</strong> (278 mg), potassium carbonate (453 mg), and N,N-dimethylformamide (3 mL) was ice cooled, and 3,5-dimethoxybenzyl bromide (541 mg) was added thereto followed by stirring at room temperature for 7 hours. To the reaction mixture, water was added followed by extraction with ethyl acetate. An organic layer obtained was washed with saturated brine, dried over anhydrous magnesium sulfate, and then filtered. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 2-chloro-5-[(3,5-dimethoxybenzyl)oxy]pyrimidine (360 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With caesium carbonate; In acetonitrile; at 20℃; for 25h; | A solution of bromide12 (231 mg, 1 mmol),diethyl (Boc-amino)malonate (275 mg,1.1 mmol) and Cs2CO3(325 mg, 1.1 mmol) in acetonitrile (4.5 mL) was stirred for25 h at room temperature. The reaction was then diluted in30 mL of ethyl acetate and extracted with water and brine.The organic phase was dried with anhydrous Na2SO4 andconcentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel, using ethylacetate/hexane (4:1) as the eluent, affording a white solid(326.2 mg, 0.77 mmol, 77% yield). mp 69.7-72.5 C;1H NMR (500 MHz, CDCl3) δ 1.29 (t, 6H, J 7.1 Hz,CO2CH2CH3), 1.47 (s, 9H, t-Bu), 3.55 (s, 2H, Ar-CH2C),3.74 (s, 6H, Ar-OCH3), 4.17-4.26 (m, 2H, CO2CH2CH3),4.27-4.36 (m, 2H, CO2CH2CH3), 5.79 (s, 1H, N-H), 6.20 (d,2H, J 2.0 Hz, Ar-H), 6.34 (t, 1H, J 2.2 Hz, Ar-H); 13C NMR(126 MHz, CDCl3) δ 14.0 (2C), 28.2 (3C), 38.5, 55.1 (2C),62.5 (2C), 67.1, 80.1, 99.1, 108.1 (2C), 137.4, 153.8, 160.5(2C), 167.6 (2C); LRMS (ESI) m/z 426.2 [M + H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 12.0h; | General procedure: To a stirred solution of intermediate 6 (100 mg, 0.433 mmol) in DMF was added K2CO3 (179 mg, 1.299 mmol) and 3-fluorobenzyl bromide (54 muL, 0.433 mmol) at RT. After stirring for 12 h, the reaction mixture was concentrated to dryness under vacuum and the residue was extracted with CH2Cl2 and water. The organic layer was washed with brine and dried over MgSO4. Then the solution was concentrated to dryness under vacuum and puried via a ash chromatography silica gel plate (petroleum ether/ethyl acetate, 3/1) to afford title compound as a pale yellow solid in 43% yield. |
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