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Type | HazMat fee for 500 gram (Estimated) |
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Structure of 1225380-31-3
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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. : | 1225380-31-3 |
Formula : | C7H6Cl2N2 |
M.W : | 189.04 |
SMILES Code : | N#CC1=NC=C(CCl)C=C1.[H]Cl |
MDL No. : | MFCD18802326 |
InChI Key : | ZFJZMAXHJRENOK-UHFFFAOYSA-N |
Pubchem ID : | 67365541 |
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#: | 1759 |
Packing Group: | Ⅱ |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 45.68 |
TPSA ? Topological Polar Surface Area: Calculated from |
36.68 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.09 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.34 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.78 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.27 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.5 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.67 |
Solubility | 0.408 mg/ml ; 0.00216 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.49 |
Solubility | 0.611 mg/ml ; 0.00323 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.12 |
Solubility | 0.145 mg/ml ; 0.000767 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 |
-5.97 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 |
0.55 |
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) |
1.82 |
* 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 |
---|---|---|
75% | With thionyl chloride; In dichloromethane; at 0 - 20℃; for 6.0h; | 272 mul (3.73 mmol) of thionyl chloride were added to a solution of 250 mg (1.86 mmol) of <strong>[58553-48-3]5-(hydroxymethyl)pyridine-2-carbonitrile</strong> [A. Ashimori et al., Chem. Pharm. Bull. 1990, 38 (9), 2446-2458] in 5 ml of anhydrous methylene chloride at 0 C. The reaction mixture was then stirred at RT for 6 h. All the volatile constituents were then removed on a rotary evaporator and the residue obtained was dried under a high vacuum. 263 mg (75% of th.) of the title compound were obtained.1H-NMR (400 MHz, CDCl3, delta/ppm): 8.73 (d, 1H), 7.90 (dd, 1H), 7.72 (d, 1H), 4.63 (s, 2H).MS (ESIpos): m/z=153/155 (35Cl/37Cl) [M+H]+.LC/MS (method F, ESIpos): Rt=0.75 min, m/z=153/155 (35Cl/37Cl) [M+H]+. |
75% | With thionyl chloride; In dichloromethane; at 0 - 20℃; for 6.0h; | Example 31A5-(Chloromethyl)pyridine-2-carbonitrile hydrochloride; 272 mul (3.73 mmol) of thionyl chloride were added to a solution of 250 mg (1.86 mmol) of <strong>[58553-48-3]5-(hydroxymethyl)pyridine-2-carbonitrile</strong> [A. Ashimori et al., Chem. Pharm. Bull. 1990, 38 (9), 2446-2458] in 5 ml of anhydrous dichloromethane at 0 C. The reaction mixture was then stirred at RT for 6 h. All the volatile constituents were then removed on a rotary evaporator and the residue obtained in this way was dried under high vacuum. 263 mg (75% of theory) of the title compound were obtained.1H-NMR (400 MHz, CDCl3, delta/ppm): 8.73 (d, 1H), 7.90 (dd, 1H), 7.72 (d, 1H), 4.63 (s, 2H).MS (ESIpos): m/z=153/155 (35Cl/37Cl) [M+H]+.LC/MS (method F, ESIpos): Rt=0.75 min, m/z=153/155 (35Cl/37Cl) [M+H]+. |
75% | With thionyl chloride; In dichloromethane; at 0 - 20℃; for 6.0h; | Example 45A 5-(Chloromethyl)pyridine-2-carbonitrile hydrochloride 272 mul (3.73 mmol) of thionyl chloride were added to a solution of 250 mg (1.86 mmol) of <strong>[58553-48-3]5-(hydroxymethyl)pyridine-2-carbonitrile</strong> [A. Ashimori et al., Chem. Pharm. Bull. 1990, 38 (9), 2446-2458] in 5 ml of anhydrous methylene chloride at 0 C. The reaction mixture was then stirred at RT for 6 h. All the volatile constituents were then removed on a rotary evaporator and the residue obtained was dried under a high vacuum. 263 mg (75% of th.) of the title compound were obtained. 1H-NMR (400 MHz, CDCl3, delta/ppm): 8.73 (d, 1H), 7.90 (dd, 1H), 7.72 (d, 1H), 4.63 (s, 2H). MS (ESIpos): m/z=153/155 (35Cl/37Cl) [M+H]+. LC/MS (method F, ESIpos): Rt=0.75 min, m/z=153/155 (35Cl/37Cl) [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48%; 47% | With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 1.0h; | .51 ml (27.14 mmol) of N,N-diisopropylethylamine and 2.87 ml (25.05 mmol) of methanesulphonic acid chloride were added successively to a solution of 2.8 g (20.87 mmol) of <strong>[58553-48-3]5-(hydroxymethyl)pyridine-2-carbonitrile</strong> [A. Ashimori et al., Chem. Pharm. Bull. 1990, 38 (9), 2446-2458] in 50 ml of anhydrous methylene chloride at 0 C. The reaction mixture was then stirred at RT for 1 h. 10 ml of water were then added, the phases were separated and the aqueous phase was extracted twice with approx. 10 ml of methylene chloride each time. The combined organic extracts were washed with saturated sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and freed from the solvent on a rotary evaporator. The residue obtained was separated into its components by means of MPLC (silica gel, mobile phase: cyclohexane/ethyl acetate 1:1). 2.12 g (48% of th.) of the title compound (for the analytical data see below) and 1.51 g (47% of th.) of the compound described in Example 40A were obtained.1H-NMR (400 MHz, CDCl3, delta/ppm): 8.76 (d, 1H), 7.93 (dd, 1H), 7.78 (d, 1H), 5.32 (s, 2H), 3.10 (s, 3H).MS (DCI, NH3): m/z=213 [M+H]+, 230 [M+NH4]+.LC/MS (method F, ESIpos): Rt=0.57 min, m/z=213 [M+H]+. |
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