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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 499770-76-2
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 499770-76-2 |
Formula : | C8H8BrN3 |
M.W : | 226.07 |
SMILES Code : | BrCC2=CC1=C([N](N=N1)C)C=C2 |
MDL No. : | MFCD03407338 |
InChI Key : | OSUZHHPMRAIJDY-UHFFFAOYSA-N |
Pubchem ID : | 2795418 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H314 |
Precautionary Statements: | P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅱ |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 51.63 |
TPSA ? Topological Polar Surface Area: Calculated from |
30.71 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.69 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.71 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.13 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.9 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.89 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.8 |
Solubility | 0.362 mg/ml ; 0.0016 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.95 |
Solubility | 2.54 mg/ml ; 0.0112 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.37 |
Solubility | 0.0976 mg/ml ; 0.000432 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 |
-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 |
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) |
2.04 |
* 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 phosphorus tribromide; In diethyl ether; at 20℃; | Phosphorus tribromide (0.230 ml, 2.45 mmol) is added to a stirred solution of (1-methyl-1 H- 1 ,2,3-benzotriazole-5-yl)methano. (0.4 g, 2.45 mmol) in diethyl ether (25 mi) under an inert atmosphere of Argon. After stirring overnight at room temperature, the reaction mixture is diluted with water (5 ml) and stirred vigorously for 10 minutes. The organic portion is <n="64"/>separated, washed with water (2 x 5 ml), brine (2 x 5 ml) and concentrated in vacuo to yield the titled product which is used crude in the next step. (MH+ 226). | |
With phosphorus tribromide; In diethyl ether; at 20℃; | 5-Bromomethyl-1-methyl-1 H-benzotriazole: Phosphorus tribromide (0.230 ml, 2.45 mmol) is added to a stirred solution of (I -methyl-I H- 1,2,3-benzotriazole-5-yl) methanol (0.4 g, 2.45 mmol) in diethyl ether (25 ml) under an inert atmosphere of Argon. After stirring overnight at room temperature, the reaction mixture is diluted with water (5 ml) and stirred vigorously for 10 minutes. The organic portion is separated, washed with water (2 x 5 ml), brine (2 x 5 ml) and concentrated in vacuo to yield the titled product which is used crude in the next step. (MH+ 226). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of (2-methyl-1 H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester ( (0.025 g, 0.122 mmol) in dry DMF (1 ml) under an inert atmosphere of Argon is added dropwise, BEMP (56.6 //I, 0.196 mmol). The mixture is agitated at room temperature for 1 hour before cooling to 0 0C with an ice-bath. A solution of 5-bromomethyl-1-methyl-1H- benzotriazole (0.044 g, 0.196 mmol) in DMF (1 ml) is added to the cooled solution and the resulting mixture is agitated at room temperature for 2 days. The solvent is removed in vacuo and purification of the crude by chromatography on silica eluting with iso- hexane/ethyl acetate (0 %- 20 % ethyl acetate) yields the titled product. (MH+ 350). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; at 140℃; for 6h; | A mixture of intermediate 18 (0.01 mol) and 5 -(bromo methyl)- 1 -methyl- IH- benzotriazole (0.0035 mol) in DMF (30ml) was stirred at 1400C for 6 hours. The solvent was evaporated. The residue was taken up in EtOAc. The organic layer was washed with water, then with saturated sodium chloride, dried (MgSO4), filtered and the solvent was evaporated. The residue was combined with another fraction made in a <n="41"/>similar way, yielding 4g, and then purified by column chromatography over silica gel (15-40mum) (eluent: DCM/MeOH 99/1). The pure fractions were collected and the solvent was evaporated. The residue (0.9g) was purified by column chromatography over silica gel (15-40mum) (eluent: DCM/MeOH 99/1). The pure fractions were collected and the solvent was evaporated, yielding 0.22g of intermediate 19. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
[2-Methyl-1-(3-methyl-3H-benzotriazol-5-ylmethyl)-1 H-pyrrolo[2,3-b]pyridin-3-yl]- acetic acid methyl ester: To a solution of (2-methyl-1 H-pyrrolo [2,3-b]pyridin-3-yl)-acetic methyl ester ( (0.025 g, 0.122 mmol) in dry DMF (1 ml) under an inert atmosphere of Argon is added dropwise, BEMP (56.6 pl, 0.196 mmol). The mixture is agitated at room temperature for 1 hour before cooling to 0 C with an ice-bath. A solution of 5-bromomethyl-1-methyl-1 H- benzotriazole (0.044 g, 0.196 mmol) in DMF (1 ml) is added to the cooled solution and the resulting mixture is agitated at room temperature for 2 days. The solvent is removed in vacuo and purification of the crude by chromatography on silica eluting with iso- hexane/ethyl acetate (0 %- 20 % ethyl acetate) yields the titled product. (MH+ 350). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetra-(n-butyl)ammonium iodide; caesium carbonate; In N,N-dimethyl-formamide; at 75℃; for 16h; | Example 305B (R)-tert-butyl 3-(5-chloro-4-(1-((1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)methyl)-1H-pyrrolo[3,2-b]pyridin-6-yl)pyridin-2-ylcarbamoyl)piperidine-1-carboxylate To a two dram vial was added Example 305A (52 mg, 0.114 mmol), <strong>[499770-76-2]5-(bromomethyl)-1-methyl-1H-benzo[d][1,2,3]triazole</strong> (51.6 mg, 0.228 mmol), cesium carbonate (111 mg, 0.342 mmol) and tetrabutylammonium iodide (42.1 mg, 0.114 mmol) in N,N-dimethylformamide (570 mul). The vial was capped with a septa and the mixture was stirred at 75 C. for 16 hours. After cooling to ambient temperature, the mixture was partitioned between water and ethyl acetate (10 mL each). The organic layer was removed and dried over anhydrous magnesium sulfate, filtered and concentrated, and purified by silica gel flash chromatography (Isco, Redi-Sep column) eluting with a gradient of 40-100% ethyl acetate/hexane to give the title compound. |