Structure of 18202-73-8
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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. : | 18202-73-8 |
Formula : | C5H13ClN2 |
M.W : | 136.62 |
SMILES Code : | CC(C)(C)C(N)=N.[H]Cl |
MDL No. : | MFCD00051988 |
Boiling Point : | No data available |
InChI Key : | ARDGQYVTLGUJII-UHFFFAOYSA-N |
Pubchem ID : | 2781880 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.8 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 39.15 |
TPSA ? Topological Polar Surface Area: Calculated from |
49.87 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.43 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.77 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.27 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.09 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.91 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.52 |
Solubility | 4.11 mg/ml ; 0.0301 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.08 |
Solubility | 1.13 mg/ml ; 0.00827 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.75 |
Solubility | 24.5 mg/ml ; 0.179 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) |
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 |
-6.12 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 |
2.0 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) |
1.6 |
* 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 |
---|---|---|
85.7% | With sodium methylate; In methanol; at 10 - 20℃; | a.1.2: 2-terf-Butvl-4-hvdroxv-6-cvclobutvl-pvrimidine; 9.2 g of tert-butyl amidinium chloride (67.3 mmol, Maybridge) and 12.6 g of methyl-2-cyclobutanoyl acetate (80.7 mmol) were dissolved/suspended in 100 ml of methanol. 14.5 g of sodium methanolate (268.4 mmol) were added in portions to the solution at 10C. The suspension was then stirred at room temperature overnight. The reaction mixture was concentrated to roughly half the volume and filtered. The filtrate was extracted with water and dichloromethane. The organic phase was dried over magnesium sulfate, filtered, and then concentrated to dryness. The residue was stirred with acetone and the precipitate was collected by filtration. Yield: 11.9 g (85.7 %).MS (ESI) m/z: 207.2 [M+H]+ |
85.7% | With sodium methylate; In methanol; at 10 - 20℃; | a.1.2: 2-terf-Butyl-4-hydroxy-6-cyclobutyl-pyrimidine; 9.2 g of te/t-butyl amidinium chloride (67.3 mmol, Maybridge) and 12.6 g of methyl-2- cyclobutanoyl acetate (80.7 mmol) were dissolved/suspended in 100 ml of methanol. 14.5 g of sodium methanolate (268.4 mmol) were added in portions to the solution at 1O0C. The suspension was then stirred at room temperature overnight. The reaction mixture was concentrated to roughly half the volume and filtered. The filtrate was ex- traded with water and dichloromethane. The organic phase was dried over magnesium sulfate, filtered, and then concentrated to dryness. The residue was stirred with acetone and the precipitate was collected by filtration. Yield: 1 1.9 g (85.7 %). EPO <DP n="20"/>MS (ESI) m/z: 207.2 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67.2% | With sodium methylate; In methanol; at 10 - 20℃; | a.2.2: 2-terf-Butvl-4-hvdroxv-6-cyclopropvl-pyrimidine; 16.3 g tert-butyl amidinium chloride (119.6 mmol, Maybridge) were dissolved/suspended in 350 ml of methanol at room temperature. 30.4 g of sodium methanolate (562.8 mmol) were added in portions to the solution at 10C,. After stirring for 30 minutes, a solution of 20 g of methyl-2-cyclopropanoyl acetate (140.7 mmol) in 150 ml of methanol was added over 2 h. The suspension was then stirred at room temperature overnight, concentrated to roughly half the volume, and filtered. 200 ml of dichloromethane were added to the filtrate and theorganic layer was washed 3 times with water. The aqueous phases were combined. The aqueous phase was adjusted to pH 3 with aq. HCI, whereby a white precipitate was formed. The precipitate was collected by filtration, redissolved in dichloromethane, dried over magnesium sulfate and filtered. The solvent was concentrated to dryness to yield 14.8 g (67.2 %) of the title compound.MS (ESI) m/z: 193.1 [M+H]+ |
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