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Type | HazMat fee for 500 gram (Estimated) |
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Structure of 130290-79-8
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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. : | 130290-79-8 |
Formula : | C6H13NO |
M.W : | 115.17 |
SMILES Code : | NCC1CCOCC1 |
MDL No. : | MFCD02179435 |
InChI Key : | IPBPLHNLRKRLPJ-UHFFFAOYSA-N |
Pubchem ID : | 2773210 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H227-H314 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 2735 |
Packing Group: | Ⅲ |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 32.63 |
TPSA ? Topological Polar Surface Area: Calculated from |
35.25 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.65 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.12 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.37 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.21 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.04 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.63 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.41 |
Solubility | 44.6 mg/ml ; 0.387 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.17 |
Solubility | 78.4 mg/ml ; 0.681 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.77 |
Solubility | 19.6 mg/ml ; 0.171 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 |
-7.09 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) |
1.42 |
* 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 |
---|---|---|
With N-ethylmorpholine;; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20.0℃; | Description 14: 6-Chloro-2-cyclopropyl-N- (tetrahydro-pyran-4-ylmethyl)-nicotinamide; To a solution of <strong>[862695-75-8]6-chloro-2-cyclopropyl-nicotinic acid</strong> (Description 13) (2. 1g) in dimethylformamide (20ml) was added 1-hydroxybenzotriazole (730mg), 1- [3- (dimethylamino) propyl] -3-ethylcarbodiimide hydrochloride (2. 31 g), N-ethyl morpholine (3. 2ml) followed by (tetrahydro-pyran-4-yl) -methylamine (1.9g). The mixture was stirred at room temperature overnight. Water (100ml) was added and the mixture was extracted with ethyl acetate (2x 100ml). The combined organic layers were washed with 10% sodium hydrogen carbonate (100ml), and brine (50ml). The dried (Na2SO4) organic layer was evaporated under reduced pressure. The residue was purified by Biotage chromatography over silica using ethyl acetate (60%) /isohexane (40%) to give the title compound (2. 81g) as a white solid. NMR (MeOD) b 0.96-1. 10 (4H, m), 1.28-1. 41 (2H, m), 1.65-1. 73 (2H, m), 1.80-1. 94 (1H, m), 2.24-2. 33 (1H, m), 3.24-3. 29 (2H, m), 3.37-3. 47 (2H, m), 3. 92-4.00 (2H, m), 7.16 (1H, d), 7.6 2 (1H, d). LC/MS t= 2. 39 min, molecular ion observed [MH] = 295 consistent with molecular formula C15H19ClN2O2 | |
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20.0℃; | Intermediate 29: 6-Chloro-2-cyclopropyl-N- (tetrahydro-pyran-4-ylmethyl)-nicotinamide; To a solution of <strong>[862695-75-8]6-chloro-2-cyclopropyl-nicotinic acid</strong> (2. 1g) in dimethylformamide (20ml) was added 1-hydroxybenzotriazole (730mg), 1- [3- (dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (2. 3 1 g), N-ethyl morpholine (3. 2ml) followed by (tetrahydro-pyran-4-yl)- methylamine (1.9g). The mixture was stirred at room temperature overnight. Water (100ml) was added and the mixture was extracted with ethyl acetate (2x 100ml). The combined organic layers were washed with 10% sodium hydrogen carbonate (100ml), and brine (50ml). The dried (Na2S04) organic layer was evaporated under reduced pressure. The residue was purified by Biotage chromatography over silica using ethyl acetate (60%) /isohexane (40%) to give the title compound (2. 81g) as a white solid. NMR (MeOD) 8 0.96-1. 10 (4H, m), 1. 28-1. 41 (2H, m), 1.65-1. 73 (2H, m), 1.80-1. 94 (1H, m), 2. 24-2. 33 ( H, m) ; 3.24-3. 29 (2H, m), 3 37 - 3. 47 (2H, m), 3.92-4. 00 (2H, m), 7.16 (1H, d), 7. 6 2 (1H, d). LC/MS t= 2. 39 min, molecular ion observed [MH] = 295 consistent with molecular formula C15Hl9CIN202 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Triethylamine (43 mL, 0.31 mol) was added in a single portion to a chilled (ice bath) suspension of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (60 g, (0.21 mol) in DMF (200 mL) to provide a solution. A solution of 1 -tetrahydro-2H-pytauan-4-ylmethylamine (36 g, 0.31 mole) in DMF (50 mL) was added dropwise. The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was chilled in an ice bath, then quenched with water (150 mL), and then stirred for 30 minutes. A solid was isolated by filtration, washed sequentially with water and diethyl ether, and then dried at 65 0C in a vacuum oven to provide 36.2 g of (7-bromo-3-nitroquinolin-4-yl)(tetrahydro-2H-pyran-4- ylmethyl)amine as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In ethanol; | General procedure: To a solution fo <strong>[579514-75-3]tert-butyl 4-fluoro-3-nitrobenzoate</strong> (560 mg, 2.3 mmol) in 20mL of EtOH were added butan-1-amine (853 mg, 11.6 mmol) and stirred at rt for 2 h.The reaction mixture was concentrated to dryness, and the residue was dissolved inEtOAc (10 x 3 mL) and washed with brine (10 mL). The combined organic layerswere dried over MgSO4, and concentrated in vacuo to afford the product tert-butyl 4-(butylamino)-3-nitrobenzoate (35b) as yellow-orange solid (490 g, 72% yield). |
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