Structure of 98141-42-5
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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. : | 98141-42-5 |
Formula : | C6H4Cl2N4 |
M.W : | 203.03 |
SMILES Code : | CN1N=CC2=C(Cl)N=C(Cl)N=C12 |
MDL No. : | MFCD09750213 |
InChI Key : | TYMWHTJGWKSXRY-UHFFFAOYSA-N |
Pubchem ID : | 222247 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H317-H319 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 46.61 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.6 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.02 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.11 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.67 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.34 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.75 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.78 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.98 |
Solubility | 0.211 mg/ml ; 0.00104 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.66 |
Solubility | 0.448 mg/ml ; 0.00221 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.97 |
Solubility | 0.22 mg/ml ; 0.00108 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 |
-6.04 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 |
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) |
1.83 |
* 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 |
---|---|---|
98% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100.0℃; for 5.0h; | A mixture of 4,6-dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (300 mg, 1.50 mmol), <strong>[114474-28-1]4-(1H-pyrazol-4-yl)aniline</strong> (235, 1.50 mmol), and iPr2NEt (0.52 mL, 0.74 mmol) in DIVIF (3.0 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (470 mg, 98%). ?H NIVIR (400 MHz, DMSO-d6) oe 12.95 (s, 1H), 10.48 (s, 1H), 8.26 (d, J 61.6 Hz, 2H), 7.95 (s, 1H), 7.84-7.51 (m, 4H), 3.91 (s, 3H). MS (ES+) m/e 326 (M+H). |
98% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100.0℃; for 5.0h; | [0233] A mixture of 4,6-dichloro-l-methyl-lH-pyrazolo[3,4-d]pyrimidine (300 mg, 1.50 mmol), 4-(lH-pyrazol-4-yl)aniline (235, 1.50 mmol), and iPr2NEt (0.52 mL, 0.74 mmol) in DMF (3.0 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (470 mg, 98%). 1H NMR (400 MHz, DMSO-i/6) delta 12.95 (s, 1H), 10.48 (s, 1H), 8.26 (d, J= 61.6 Hz, 2H), 7.95 (s, 1H), 7.84 - 7.51 (m, 4H), 3.91 (s, 3H). MS (ES+) m/e 326 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; at 50℃; | To a solution of commercially available 4,6-dichloro- 1-methyl- 1H-pyrazolo[3,4-djpyrimidine (50 mg, 0.246 mmol) and <strong>[15996-84-6]1-(4-(trifluoromethyl)phenyl)ethanamine</strong> (51.2 mg, 0.271 mmol) in THF(2463 iL) was added TEA (51.5 tl) and the resulting mixture stirred at 50C for 40 minutes. Desired product was seen after 40 minutes via aliquot analyzed by LCMS and it was observed that about 75% desired product formed. The reaction was allowed to stir at 50C overnight to ensure completion. The mixture was cooled to room temperature and the mixture concentrated under reduced pressure. The residue was purified on ISCO normal phase (12g silica gel gold Redi-Sep column, 0-5% MeOH in DCM) to afford the title compound as a solid.LC-MS (+ESI) m/z = 356.1and 358.0 (M+2+H). ‘H NMR (500 MHz, MeOH-d4) ö: 7.68-7.60 (m, 2H), 7.57-7.48 (m, 2H), 5.35 (s, 1H), 4.18-4.09 (m, 1H), 3.96 (s, 3H), 1.65 (s, 3H). |
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