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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 172649-57-9
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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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CAS No. : | 172649-57-9 |
Formula : | C4H4ClNO |
M.W : | 117.53 |
SMILES Code : | ClCC1=CN=CO1 |
MDL No. : | MFCD07778417 |
InChI Key : | UJLHZLUVPVJDQI-UHFFFAOYSA-N |
Pubchem ID : | 15290880 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H315-H318-H335-H227 |
Precautionary Statements: | P210-P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501 |
Class: | 8 |
UN#: | 3265 |
Packing Group: | Ⅲ |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 26.27 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.03 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.45 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.76 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.26 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.06 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.88 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.06 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.51 |
Solubility | 3.63 mg/ml ; 0.0309 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.89 |
Solubility | 15.3 mg/ml ; 0.13 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.21 |
Solubility | 0.73 mg/ml ; 0.00621 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 |
-6.48 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) |
1.93 |
* 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 |
---|---|---|
E. 5-(Chloromethyl)oxazole Using the procedure of Example 1Q, but replacing 5-(hydroxymethyl)thiazole with 5-(hydroxymethyl)oxazole provided the desired compound. | ||
With thionyl chloride; In hexane; dichloromethane; at 0℃; for 3.0h;Inert atmosphere; Reflux; | [000283] Synthesis of 5-(chloromethyl) oxazole (344): To a stirred solution of compound 343 (800 mg, 8.08 mmol) in CH2C12: n-hexane (1: 1, 10 mL) under argon atmosphere was added thionyl chloride (1.2 mL, 16.16 mmol) at 0 C; heated to reflux and stirred for 3 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was neutralized with saturated NaHCO3 solution (20 mL) and extracted with ether (2 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude compound 344 (700 mg) as colorless syrup. TLC: 40% EtOAc/ hexanes (R 0.5); 1H- NMR (CDC13, 400 MHz): oe 7.89 (s, 1H), 7.10 (s, 1H), 4.62 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium chloride; In diethyl ether; ethanol; hexane; ethyl acetate; mineral oil; | 301 mg of a 60% dispersion of sodium hydride in mineral oil were added portionwise to 60 ml of anhydrous ethanol at 0 C. and the resulting suspension was stirred at 0 C. for 5 minutes. 1.88 g of diethyl 2-(tert-butoxyformamido)malonate were added and the mixture was warmed to room temperature. After stirring at room temperature for 10 minutes 805 mg of <strong>[172649-57-9]5-(chloromethyl)oxazole</strong> were added. The mixture was stirred at room temperature for 30 minutes and at 60 C. for 1 hour. The solvent was evaporated and the crude product was dissolved in diethyl ether and washed with water. Sodium chloride was added to the aqueous layer, which was then extracted with diethyl ether. The combined organic layers were dried over magnesium sulphate and the solvent was removed by evaporation. Purification of the residue by chromatography on silica gel using ethyl acetate/hexane (1:2) for the elution gave diethyl 2-(tert-butoxyformamido)-2-[(5-oxazolyl)methyl]malonate, 1H NMR (250 MHz, CDCl3) delta: 1.3 (t,6H), 1.45 (s,9H), 3.75 (s,2H), 4.2 (m,4H), 5.85 (s,1H), 6.8 (s,1H), 7.75 (s,1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; | General procedure: A solution ofthiophen-2-ylmethanol (200 mg, 1.75 mmol), diisopropylethylamine (DIEA,453 mg, 612 )lL, 3.5 mmol) in DCM (5 mL) was cooled to 0 C, MsCl (163 )lL, 2.1 mmol) wasadded and the mixture warmed to RT. After 2 h H20 and DCM were added, the organic layerseparated and washed with sat. NH4Cl, H20, sat. NaHC03, dried with MgS04 and concentrated togive the title compound (203 mg, light brown oil) which was used without purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; at 20 - 70℃; for 4.0h;Inert atmosphere; | [000284j Synthesis of 2-(oxazol-5-yl) acetonitrile (345): To a stirred solution of compound 344 (700 mg, 5.95 mmol) in DMF (8 mL) under argon atmosphere was added sodium cyanide (1.02 g, 20.85 mmol) at RT; heated to 70 C and stirred for 4 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with ether (2 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude compound 345 (650 mg) as colorless syrup. TLC: 40% EtOAc/ hexanes (R 0.3); 1H-NMR (CDC13, 400 MHz): oe 7.89 (s, 1H), 7.10 (s, 1H), 3.84 (s, 2H). |