Structure of 113713-60-3
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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.
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CAS No. : | 113713-60-3 |
Formula : | C7H7N3OS |
M.W : | 181.22 |
SMILES Code : | COC2=CC=C1N=C([NH]C1=N2)S |
MDL No. : | MFCD06658230 |
InChI Key : | PNYFSMIUARCIRR-UHFFFAOYSA-N |
Pubchem ID : | 11126879 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 47.63 |
TPSA ? Topological Polar Surface Area: Calculated from |
89.6 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.59 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.54 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.26 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.6 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.78 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.35 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.42 |
Solubility | 0.685 mg/ml ; 0.00378 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.03 |
Solubility | 0.169 mg/ml ; 0.000931 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.78 |
Solubility | 0.304 mg/ml ; 0.00167 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) |
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 |
-6.31 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) |
1.81 |
* 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 |
---|---|---|
0.187 g | Compound 9c was obtained as described17 using 2,6-dichloropyridine as the starting material in five steps, including methoxylation, nitration, amination, reduction, and cyclization. The overall yield of this sequence was up to 45.7%. The structure of the product was identified by 1H NMR, MS, and IR. A solution of 0.5 g (3 mmol) 6-methoxy-3-nitropyridine-2-amine 100 ml CH3OH, 2 ml H2O, and 0.1 g Pd/C (10%) are allowed to shake with H2 (3 bar) in a hydrogenation apparatus until constant pressure. After filtration, the product solution is heated with 1 ml CS2 and 0.225 g KOH until reflux. When the reaction is completed (TLC control) the solvent is evaporated under reduced pressure. The resulted solid is recrystallized from ethanol. Yield: 0.187 g (1.1 mmol), 35%, mp: 223-225 C. IR: inlMMLBox (cm-1) = 3262; 3051; 1624. 1H NMR: (200 MHz, DMSO-d6) delta (ppm) = 12.99 (s, 1H, NH); 12.54 (s, 1H, NH); 7.43-7.47 (d, 1H, J = 8.5 Hz, H arom.); 6.55-6.60 (d, 1H, J = 8.5 Hz, H arom.); 3.83 (s, 3H, CH3). 13C NMR: (50 MHz, DMSO-d6) delta (ppm) = 167.60; 160.12; 143.62; 120.17; 119.65; 103.90; 53.49 | |
16.9 g | With potassium hydroxide; In ethanol; water; for 12.0h;Reflux; | To a solution of compound 2 (20.56 g, 148 mmol) in a mixture of EtOH (200 mL) and water (40 mL) was added KOH (9.75 g, 148 mmol) and CS2 (22.5 g, 296 mmol). The reaction mixture was stirred at reflux for 12 h. The solvents were evaporated, and the residue was purified by column chromatography on silica gel with eluent (2:98 to 10:90 MeOH/CH2Cl2), affording a gray solid product 3 (16.9 g, 63%). Rf = 0.50 (1:19 MeOH/CH2Cl2), mp 246-248 C. 1H NMR (DMSO-d6): delta 3.83 (s, 3H, OCH3), 6.56 (d, J = 8.5 Hz, 1H, Ar-H), 7.44 (d, J = 8.5 Hz, 1H, Ar-H), 12.73 (s, 2H, NH). MS (ESI): 182 ([M+H]+, 100%); MS (ESI): 180 ([M-H]-, 23%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In ethanol; water; at 20℃; | General procedure: To a solution of compound 3 (360 mg, 2.0 mmol) in a mixture of EtOH (60 mL) and 1 N aq NaOH (2.2 mL, 2.2 mmol), compound 1 (2.1 mmol) was added. The resulting reaction mixture was stirred overnight at rt. Then solvents were removed under reduced pressure, and the crude product was purified by column chromatography on silica gel with eluent (0:100 to 3:97 MeOH/CH2Cl2) to give a white solid product 4 (50-65% yields). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In ethanol; water; at 20℃; | General procedure: To a solution of compound 3 (360 mg, 2.0 mmol) in a mixture of EtOH (60 mL) and 1 N aq NaOH (2.2 mL, 2.2 mmol), compound 1 (2.1 mmol) was added. The resulting reaction mixture was stirred overnight at rt. Then solvents were removed under reduced pressure, and the crude product was purified by column chromatography on silica gel with eluent (0:100 to 3:97 MeOH/CH2Cl2) to give a white solid product 4 (50-65% yields). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In ethanol; water; at 20℃; | General procedure: To a solution of compound 3 (360 mg, 2.0 mmol) in a mixture of EtOH (60 mL) and 1 N aq NaOH (2.2 mL, 2.2 mmol), compound 1 (2.1 mmol) was added. The resulting reaction mixture was stirred overnight at rt. Then solvents were removed under reduced pressure, and the crude product was purified by column chromatography on silica gel with eluent (0:100 to 3:97 MeOH/CH2Cl2) to give a white solid product 4 (50-65% yields). |
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