Structure of 158261-95-1
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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 158261-95-1 |
Formula : | C8H17NO |
M.W : | 143.23 |
SMILES Code : | CC(N1CCCC1)CCO |
MDL No. : | MFCD09864547 |
InChI Key : | FKCMGWYAPOCAKE-UHFFFAOYSA-N |
Pubchem ID : | 10012019 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 46.43 |
TPSA ? Topological Polar Surface Area: Calculated from |
23.47 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.2 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.86 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.47 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.9 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.25 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.14 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.07 |
Solubility | 12.1 mg/ml ; 0.0848 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.94 |
Solubility | 16.6 mg/ml ; 0.116 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.97 |
Solubility | 15.3 mg/ml ; 0.107 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 |
-6.56 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 |
---|---|---|
73% | Intermediate 25: 3-Pyrrolidin-1-yl-butan-1-ol; [] Pyrrolidine (28.15g, 0.4mol), toluene (200ml), catalytic p-TsOH (200mg) and ethyl acetoacetate (20g, 0.15mol) were refluxed together in a Dean-Stark apparatus under N2 for 3hours. The reaction was cooled to room temperature and concentrated in vacuo. NaBH4 (3.1 g, 82mmol) was dissolved in MeOH (50ml) and cooled to 0-5C. A portion of the previous crude reaction (5g, 27mmol) in MeOH (25ml) was added to the reaction mixture and stirred for 72hours. The reaction was quenched with an aqueous solution of NaOH (1%w/w, 50ml) and concentrated in vacuo. The aqueous phase was extracted with TBME (3 x 50ml). The combined organic extracts were dried over MgSO4, filtered, washed with TBME and concentrated in vacuo to give a mixture of the title compound, 3-pyrrolidin-1-yl-butanoic acid ethyl ester and residual TBME (3.5g). The mixture (3.5g) in THF (20ml) was added to a solution of LiALH4 (1 M in THF, 33.5ml, 33.5mmol) at 0-5C under N2. The reaction was allowed to warm to room temperature and stirred for 3hours. The reaction was quenched with an aqueous solution of NaOH (1%w/w, 50ml) at 0-5C, filtered and washed with THF (3 x 20ml). The combined organic layers were dried over MgSO4, filtered, washed with THF and concentrated in vacuo to give the title compound as a yellow oil (2g, 73%th).1H NMR (400MHz, CDCl3) δ5.98 (br s, 1 H), 3.90 (ddd, 1 H), 3.77 (ddd, 1 H), 2.90 (m, 1 H), 2.70-2.55 (m, 4H), 1.80-1.56 (m, 6H), 1.09 (d, 3H).; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With thionyl chloride; In dichloromethane; at 0 - 20℃; | Step 2:; 3-Pyrrolidin-1-yl-butan-1-ol (1.0g, 7mmol) was dissolved in DCM (20ml). The reaction was cooled to 0-5C and thionyl chloride (1.65g, 14mmol) was added slowly. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was concentrated in vacuo and azeo-dried with DCM (20ml) to give the title compound (1.4g, 100%th) as a brown oil.1H NMR (400MHz, CDCl3) δ12.45 (br s, 1 H), 3.84-3.71 (m, 3H), 3.56 (m, 1H), 3.38 (m, 1 H), 2.92-2.79 (m, 2H), 2.45-1.99 (m, 6H), 1.51 (d, 3H). |