Structure of 13438-65-8
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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. : | 13438-65-8 |
Formula : | C6H7N3O |
M.W : | 137.14 |
SMILES Code : | O=C(N)C1=C(N)N=CC=C1 |
MDL No. : | MFCD00128873 |
InChI Key : | HTPCDVLWYUXWQR-UHFFFAOYSA-N |
Pubchem ID : | 506623 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H317-H319 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 36.74 |
TPSA ? Topological Polar Surface Area: Calculated from |
82.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.61 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.88 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.23 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.61 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.21 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.09 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.62 |
Solubility | 3.27 mg/ml ; 0.0238 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.19 |
Solubility | 0.893 mg/ml ; 0.00651 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.23 |
Solubility | 8.15 mg/ml ; 0.0594 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 |
-6.51 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) |
1.3 |
* 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 |
---|---|---|
In N,N-dimethyl-formamide; at 80℃; for 14h; | Example 122 1-(2,5-dichlorobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide To a solution of 2-aminonicotinamide (0.2 g) in N,N-dimethylformamide (5 ml) was added <strong>[85482-13-9]2,5-dichlorobenzylbromide</strong> (0.39 g) (Table 2, bromide 122), and the mixture was stirred at 80C for 14 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (0.21 g). 1H-NMR (DMSO-d6) d ppm 5.52 (2 H, s) 6.95 (1 H, d, J=2.27 Hz) 7.06 - 7.17 (1 H, m) 7.50 - 7.59 (1 H, m) 7.63 - 7.71 (1 H, m) 8.13 (1 H, s) 8.23 (1 H, d, J=5.30 Hz) 8.52 (1 H, d, J=6.82 Hz) 8.59 (1 H, s) 9.45 (2 H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; at 80℃; for 14h; | Example 134 1-(3,5-dichlorobenzyl)-2imino-1,2-dihydropyridine-3-carboxamide hydrochloride To a solution of 2-aminonicotinamide (0.18 g) in N,N-dimethylformamide (3 ml) was added <strong>[3290-06-0]3,5-dichlorobenzyl chloride</strong> (0.31 g), and the mixture was stirred at 80°C for 14 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (0.10 g). 1H-NMR (DMSO-d6) d ppm 5.62 (2 H, s) 7.12 (1 H, t, J=7.19 Hz) 7.42 (2 H, d, J=1.51 Hz) 7.66 (1 H, s) 8.09 (1 H, s) 8.44 (1 H, d, J=6.06 Hz) 8.55 (1 H, d, J=7.57 Hz) 8.64 (1 H, s) 9.49 (2 H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With ytterbium(III) triflate; In 1,3,5-trimethyl-benzene; at 165℃; for 6h;Inert atmosphere; | General procedure: A mixture of 2-aminobenzamide (1, 4.0 mmol), carboxamide (2, 6.0 mmol), Yb(OTf)3 (0.20 mmol,5.0 mol%), and mesitylene (5.0 mL) was placed in a 20-mL Pyrex flask equipped with a magnetic stirring bar and a reflux condenser under a flow of argon. The reaction was carried out at 120-165 oC (bath temp.) for 6 h with stirring. Then, the reaction mixture was cooled to room temperature, and analyzed by GLC, GC-MS (EI), and LC-MS (ESI). After evaporation of mesitylene under vacuum,the products (3) were isolated by recrystallization from MeOH/hexane and/or medium pressure column chromatography on silica gel (eluent: EtOAc/hexane = 50/50 ~ EtOAc 100%. For 3j, eluent:MeOH/CHCl3 = 50/50). 1H NMR spectra were recorded at 400 MHz, and 13C NMR spectra wererecorded at 100 MHz in DMSO-d6. The analytical and spectral data of 3a-e,38 3f,39 3g,40 3h,41 and3j,42 were consistent with those reported previously. The product, 3i, was characterized below. |
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