Structure of 273-34-7
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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. : | 273-34-7 |
Formula : | C5H4N4 |
M.W : | 120.11 |
SMILES Code : | N1N=NC2=C1N=CC=C2 |
MDL No. : | MFCD01659957 |
InChI Key : | VQNDBXJTIJKJPV-UHFFFAOYSA-N |
Pubchem ID : | 136085 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 31.68 |
TPSA ? Topological Polar Surface Area: Calculated from |
54.46 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.66 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.36 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.35 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.15 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.23 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.55 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.55 |
Solubility | 3.37 mg/ml ; 0.0281 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.07 |
Solubility | 10.3 mg/ml ; 0.0854 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.12 |
Solubility | 0.917 mg/ml ; 0.00764 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 |
No |
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 |
-6.78 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 |
0.0 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) |
1.74 |
* 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 |
---|---|---|
30% | Example 104 4-(3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)quinazoline To a solution of a hydroxyquinazoline (400 mg, 2.73 mmol), and BOP (1450 mg, 3.2 mmol) was added DBU (0.61 mL, 4.09 mmol) at room temperature under nitrogen. The resultant mixture was stirred for 5-10 min at room temperature, after which 3H-[1,2,3 <strong>[273-34-7]triazolo[4,5-b]pyridine</strong> (714 mg, 6.0 mmol) was added. The reaction mixture was monitored by LCMS till complete consumption of starting material (30 hrs). The solvent was removed under vacuum, the crude reaction mixture was purified by a flash chromatography on SiO2 column eluted with hexanes/EtOAc to give the desired product (200 mg, 30%). 1H-NMR (CDCl3, 400 MHz) delta (ppm) 9.43 (s, 1H), 9.01 (d, 1H, J=8.4 Hz), 8.93 (m, 2H), 8.22-8.19 (m, 2H), 7.99-7.96 (m, 1H), 7.87 (dd, 1H, J=8.0 Hz, J=4.4 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; | To a stirred solution of compound 1C (30 mg, 0.12 mmol) in anhydrous THF (3.0 mL) were sequentially added compound ID (28 mg, 0.23 mmol) and triphenyl phosphine (61 mg, 0.23 mmol). The reaction mixture was cooled to 00C, and to it diisopropyl-azodicarboxylate (0.05 mL, 0.23 mmol) was added in drop wise manner. After the addition was over, stirring continued for another 0.5 h at 00C and then for 12 h at room temperature. Solvents were removed in vacuum and the residue was purified by preparative HPLC to provide compounds 1 and 2 as TFA salts. ESI-MS for both compounds:m/z 362.1 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24%; 38%; 16% | With triethylamine; In N,N-dimethyl-formamide; for 12h;Reflux; | General procedure: 2g (16.6mmol) of the appropriate 3H-[1,2,3]triazolo[4,5-b/c]pyridine (1a,b) were dissolved in 20ml of dimethylformamide (DMF). 1.95g (19.4mmol) 2.68ml of triethylamine and 2g (26.5mmol) 1.69ml of chloroacetonitrile were added to the resultant solution. The whole mixture was heated under reflux for 12h. After cooling, the triethylamine hydrochloride formed was filtered, and the solution was evaporated to dryness. The residue, dissolved in ether, was washes with water. Through evaporation of the extract, a residue containing the three isomers 2-4a or 2-4b was obtained. Isomers were separated by flash chromatography, elution with light petroleum-ethyl acetate 80:20 afforded desired compounds. 9.1.2.1 <strong>[273-34-7]3H-[1,2,3]<strong>[273-34-7]triazolo[4,5-b]pyridine</strong></strong>-3-carbonitrile (2a) Yield: 24%. M.p.: 56.8-57 C. 1H NMR (DMSO-d6): delta 8.86 (d, 1H, CH-5. J = 4.0 Hz); 8.66 (d, 1H, CH-7. J = 8.8 Hz); 7.61 (m, 1H, CH-6); 6.14 (s, 2H, CH2). 13C NMR (CDCl3): delta 151.53 (CH); 144.76 (C); 136.18 (C); 129.18 (CH); 120.96 (CH); 114.73 (C); 34. 27 (CH2). GC/MS: 146 (M + H). Anal. Calcd for (C6H3N5): C, 49.66; H, 2.08; N, 48.26. Found: C, 49.56; H, 2.19; N, 48.23. 9.1.2.2 2H-[1,2,3]<strong>[273-34-7]triazolo[4,5-b]pyridine</strong>-2-carbonitrile (3a) (0038) Yield: 16%. M.p.: 98.6-100C. 1H NMR (DMSO-d6): delta 8.89 (d, 1H, CH-5, J=4.0Hz); 8.53 (d, 1H, CH-7, J=8.8Hz); 7.61-7.55 (m, 1H, CH-6); 6.34 (s, 2H, CH2). 13C NMR (CDCl3): delta 155.15 (C); 153.21 (CH); 128.01 (C); 136.52 (C); 127.57 (CH); 123.41(CH); 114.06 (C); 44.57 (CH2). GC/MS: 146 (M+H). Anal. Calcd for (C6H3N5): C, 49.66; H, 2.08; N, 48.26. Found: C, 49.61; H, 2.10; N, 48.18. 9.1.2.3 1H-[1,2,3]<strong>[273-34-7]triazolo[4,5-b]pyridine</strong>-1-carbonitrile (4a) (0039) Yield: 38%. M.p.: 160-160.5C. 1H NMR (DMSO-d6): delta 8.80 (d, 1H, CH-5, J=4Hz); 8.50 (d, 1H, CH-7, J=8.4); 7.74-7.70 (m, 1H, CH-6); 6.22 (s, 2H, CH2). 13C NMR (CDCl3): delta 156.54 (C); 148.89 (CH); 125.16 (C); 123.30 (CH); 120.12 (CH); 114.79 (C); 36.38 (CH2). GC/MS: 146 (M+H). Anal. Calcd for (C6H3N5): C, 49.66; H, 2.08; N, 48.26. Found: C, 49.59; H, 2.15; N, 48.24. |
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