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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+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Structure of 936368-68-2
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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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Search for reports by entering the product batch number.
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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'.
Search for reports by entering the product batch number.
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CAS No. : | 936368-68-2 |
Formula : | C14H20ClN3O2 |
M.W : | 297.78 |
SMILES Code : | O=C(N1CCN(C2=NC=CC(Cl)=C2)CC1)OC(C)(C)C |
MDL No. : | MFCD14702604 |
InChI Key : | PROPFBXURCWWDT-UHFFFAOYSA-N |
Pubchem ID : | 68535175 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H301-H311-H331 |
Precautionary Statements: | P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 |
Class: | 6.1 |
UN#: | 2811 |
Packing Group: | Ⅲ |
Num. heavy atoms | 20 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.57 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 86.45 |
TPSA ? Topological Polar Surface Area: Calculated from |
45.67 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.14 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.6 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.03 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.04 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.76 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.32 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.28 |
Solubility | 0.155 mg/ml ; 0.000522 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.21 |
Solubility | 0.184 mg/ml ; 0.000619 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.31 |
Solubility | 0.145 mg/ml ; 0.000488 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) |
Yes |
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) |
Yes |
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 |
-6.27 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 |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.59 |
* 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 |
---|---|---|
With sodium t-butanolate;palladium diacetate; johnphos; In toluene; at 100.0℃; for 4.0h; | Step A: Stir a solution of 2,4-dichloro-pyridine (6.7 mmol, 1 g), N-Boc piperazine (8.1 mmol, 1.5 g), sodium tert butoxide (9.5 mmol, 0.9 g), palladium (II) acetate (0.7 mmol, 0.15 g) and 2-(di- tbutylphosphino)biphenyl (0.7 mmol, 0.2 g) dissolved in toluene under nitrogen at 100 C for 4 hours. Cool down to room temperature and add water. Extract in ethyl acetate washing the organic layer with water and saturated aq. sodium chloride. Dry organic layer over sodium sulfate, filter, and concentrate under reduced pressure to give 4-(4-chloro-ρyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester as a residue. Subject residue to silica gel chromatography eluting with hexanes / ethyl acetate in gradient (from 10% to 50%). MS(ES): m/z = 298 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In 1,4-dioxane; dichloromethane; | Step B: Treat a room temperature solution of 4-(4-chloro-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester (0.6 g, 1.9 mmol) in CH2CL2 (4 mL) with HCl (4 N solution in dioxane, 1.5 mL, 5.9 mmol) resulting in a slight exotherm. Stir the mixture for 3 hours, add additional HCl (4 N solution in dioxane, 1.5 mL, 5.9 mmol), and stir overnight. Concentrate under reduced pressure to afford l-(4-chloro- pyridin-2-yl)-piperazine hydrochloride, then titurate with Et2O (0.43 g). LCMS ES+ (m/z) 198 [M+H]). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22%; 51% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 120.0℃; | 2,4-Dichloropyridine (1.00 g, 6.7 mmol) and piperazine-1-carboxylic acid tert-butyl ester (1.64 g, 8.8 mmol) were suspended in DMF (10 ml) and iPr2NEt (2.30 ml, 14 mmol) was added. After stirring over night at 120 C. the reaction mixture was diluted with H2O and extracted with EtOAc. The organic layer was dried (Na2SO4) and the solvent was evaporated. The residue was purified by flash chromatography (SiO2 50 g, nHept/EtOAc 5 to 100%) to yield 1.02 g (51%) of product and 450 mg (22%) of the regioisomer as byproduct. Light yellow solid. m/z: 298.4 ([M+H]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; In toluene; at 80.0℃; for 12.0h;Inert atmosphere; | General procedure: Put 1-bromo-2,3-dichlorobenzene (1.35g, 6mmol), (R)-2-methylpiperazine-1-carboxylic acid tert-butyl ester (836mg, 5mmol), three ( Dibenzylideneacetone) two palladium (228mg, 0.25mmol), 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene (289mg, 0.5mmol), sodium tert-butoxide (1.44 g, 15 mmol) was dissolved in 20 ml of toluene, and the reaction solution was replaced with nitrogen.The reaction was stirred at 80C for 12 hours under nitrogen protection.After the reaction was completed, the reaction system was cooled to room temperature, the reaction was quenched with water, and extracted with ethyl acetate (10 mL*3).The organic phase was washed with water and saturated brine, and dried with anhydrous sodium sulfate.Filter, spin dry, and separate the crude product by column chromatography (petroleum ether/ethyl acetate = 4/1 rinse) to obtain |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
500 mg | With N-chloro-succinimide; acetic acid; In chloroform; at 70.0℃; for 6.0h;Inert atmosphere; | Put tert-butyl 4-(2-chloropyridin-4-yl)piperazine-1-carboxylate (1.5g, 5.1mmol), N-chlorosuccinimide (0.8g , 6.1mmol), acetic acid (6ml) was dissolved in 20ml chloroform, and the reaction solution was replaced with nitrogen.The reaction was stirred at 70C for 6 hours under nitrogen protection.After the completion of the reaction, the reaction system was cooled to room temperature and spin-dried. The crude product was separated by column chromatography (petroleum ether/ethyl acetate = 4/1 flushing) to obtain tert-butyl 4-(4,5-dichloropyridine-2) -Yl)piperazine-1-carboxylate (500 mg). |