Structure of 905306-69-6
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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. : | 905306-69-6 |
Formula : | C7H10N2O |
M.W : | 138.17 |
SMILES Code : | NCC1=NC=C(OC)C=C1 |
MDL No. : | MFCD10697534 |
InChI Key : | AKYKNKLVGMYOIL-UHFFFAOYSA-N |
Pubchem ID : | 17854247 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.29 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 38.4 |
TPSA ? Topological Polar Surface Area: Calculated from |
48.14 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.61 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.28 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.4 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.39 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.93 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.45 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.83 |
Solubility | 20.3 mg/ml ; 0.147 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.27 |
Solubility | 73.9 mg/ml ; 0.535 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.17 |
Solubility | 0.936 mg/ml ; 0.00678 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 |
-7.34 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) |
1.62 |
* 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% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 50℃; for 10h; | To a solution of <strong>[905306-69-6]1-<strong>[905306-69-6](5-methoxypyridin-2-yl)methanamine</strong></strong> (138 mg, 1 mmol) and 2-chloro-3-methyl-7-(propan-2-yl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one (90 mg, 0.4 mmol) in DMF (1.5 mL) was added DIEA (104 mg, 0.8 mmol). The reaction mixture was stirred at 50C for 10 h and purified by preparative HPLC (MeCN and H2O with 0.01% NH3.H2O as mobile phase) to give the titled compound (40 mg, yield 30 %).LC-MS (m/z) = 329 [M + H]+.1H-NMR (400 MHz, DMSO-d6): delta 1.40 (d, J = 7.2 Hz, 6H), 3.46-3.52 (m, 1H), 3.53 (s, 3H), 3.89 (s, 3H), 4.55 (d, J = 4.0 Hz, 2H), 6.07 (s, 1H), 7.27-7.31 (m, 2H), 7.75 (s, 1H), 8.26 (d, J = 2.4 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | To a mixture of (R) -2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2-phenylpropanoic acid (50 mg, 0.13 mmol) , and DIPEA (70 mg, 0.54 mmol) in THF (1 mL) was added HATU (54 mg, 0.14 mmol) at rt and the mixture was stirred at rt for 10 min. A solution of (5-methoxypyridin-2-yl) methanamine (20 mg, 0.14 mmol) was added, and the mixture was stirred at rt for 16 hrs. The mixture was diluted with 5 mL of EtOAc, washed with brine (3 mL x 3) , dried over Na 2SO 4, and concentrated. The resulted residue was purified by prep-TLC (EtOAc, 100%) and the resulted solid was lyophilized to give the title product (45 mg, yield: 69%) . 1H NMR (400 MHz, DMSO-d6) delta 8.25 (s, 1H) , 8.17 -8.07 (m, 2H) , 8.02 (s, 2H) , 7.97 -7.92 (m, 1H) , 7.38 -7.26 (m, 5H) , 7.26 -7.19 (m, 3H) , 6.74 (dd, J = 3.2, 1.6 Hz, 1H) , 4.46 -4.26 (m, 2H) , 3.78 (s, 3H) , 2.38 (s, 3H) . MS: M/e 510 (M+1) +. |
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