Structure of Methyl 6-aminohexanoate HCl
CAS No.: 1926-80-3
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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. : | 1926-80-3 |
Formula : | C7H16ClNO2 |
M.W : | 181.66 |
SMILES Code : | O=C(OC)CCCCCN.[H]Cl |
MDL No. : | MFCD00035455 |
InChI Key : | YSLDOTFAFZJPOC-UHFFFAOYSA-N |
Pubchem ID : | 11499324 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.86 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 46.72 |
TPSA ? Topological Polar Surface Area: Calculated from |
52.32 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 |
0.46 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.48 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.08 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.74 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.75 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.86 |
Solubility | 25.1 mg/ml ; 0.138 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.13 |
Solubility | 13.6 mg/ml ; 0.0746 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.6 |
Solubility | 4.57 mg/ml ; 0.0252 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 |
-7.08 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) |
1.45 |
* 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 |
---|---|---|
76% | With triethylamine; In water; acetonitrile; | Example 236 6-(Pyridine-3-sulfonylamino)hexanoic acid methyl ester (93c) Pyridine-3-sulfonyl chloride hydrochloride (92c) (1.8 g, 5.0 mmol) was added to a solution of methyl 6-aminohexanoate hydrochloride (91) (1.82 g, 10 mmol) and triethylamine (3.03 g, 30 mmol) in acetonitrile (30 ml). The mixture was stirred for 1 hour at ambient temperature, filtered and solvents were removed under reduced pressure. The oily product was dissolved in water (15 ml) and extracted with ethyl ether (50 ml). The extract was dried (Na2SO4) and the solvents were removed under reduced pressure. The title compound (1.09 g, 76percent) was obtained as oil and was used for the next step without an additional purification. 1H NMR deltaH (90 MHz, DMSO-d6) delta: 0.80-1.51 (6H, m, CH2); 1.83 (2H, t, J=6.5 Hz, CH2); 2.76 (2H, t, J=6.5 Hz, CH2N); 3.58 (3H, s, CH3); 7.54 (1H, dd, J=5.0 Hz, J=8.2 Hz, C5HN 8.12 (1H, dt, J=2.0 Hz, J=8.2 Hz, C5HN); 8.61 (1H, dd, J=2.0 Hz, J=5.0 Hz, C5HN); 8.81 (1H, d, J=2.0 Hz, C5HN). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 0 - 20℃; for 1h; | To a solution of 6-methoxy-6-oxohexan-l-aminium chloride (0.3 g) and triethylamine (1.15 mL) in dichloromethane at 0 C was dropwise added <strong>[6608-47-5]ethenesulfonyl chloride</strong> (0.209 g). The reaction mixture was warmed to room temperature and stirred for 1 hour. The mixture was diluted with dichloromethane and washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to provide the title compound. MS (ESI) m/e 471.0 (2M+H)+. | |
With triethylamine; In dichloromethane; at 0 - 20℃; for 1h; | [0001020] To a solution of 6-methoxy-6-oxohexan-l-aminium chloride (0.3 g) and triethylamine (1.15 mL) in dichloromethane at 0 C was added <strong>[6608-47-5]ethenesulfonyl chloride</strong> (0.209 g) dropwise. The reaction mixture was warmed to room temperature and stirred for 1 hour. The mixture was diluted with dichloromethane and washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to provide the title compound. MS (ESI) m/e 471.0 (2M+H)+. | |
With triethylamine; In dichloromethane; at 0 - 20℃; for 1h; | To a solution of 6-methoxy-6-oxohexan-1-aminium chloride (0.3 g) and triethylamine (1.15 mL) in dichloromethane at 0 C was added <strong>[6608-47-5]ethenesulfonyl chloride</strong> (0.209 g) dropwise. The reaction mixture was warmed to room temperature and stirred for 1 hour. The mixture was diluted with dichloromethane and washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to provide the title compound. MS (ESI) m/e 471.0 (2M+H)+. |
With triethylamine; In dichloromethane; at 0 - 20℃; for 1h; | To a solution of 6-methoxy-6-oxohexan-I-aminium chloride (0.3 g) and triethylamine25 (l.I5 mL) in dichloromethane at 0 oc was added <strong>[6608-47-5]ethenesulfonyl chloride</strong> (0.209 g) dropwise. Thereaction mixture was warmed to room temperature and stirred for I hour. The mixture was dilutedwith dichloromethane and washed with brine. The organic layer was dried over sodium sulfate,filtered, and concentrated to provide the title compound. MS (ESI) m/e 471.0 (2M+Ht. | |
With triethylamine; In dichloromethane; at 0 - 20℃; for 1h; | To a solution of 6-methoxy-6-oxohexan-1-arninium chloride (0.3 g) and triethylarnine (1.15 mL) indichioromethane at 0 C was dropwise added <strong>[6608-47-5]ethenesulfonyl chloride</strong> (0.209 g). The reaction mixturewas warmed to room temperature and stirred for 1 hour. The mixture was diluted withdichioromethane and washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to provide the title compound. MS (ESI) rn/c 471.0 (2M+H). | |
With triethylamine; In dichloromethane; at 0 - 20℃; for 1h; | To a solution of 6-methoxy-6-oxohexan-1-aminium chloride (0.3 g) and triethylamine (1.15 mL) in dichloromethane at 0 C. was added <strong>[6608-47-5]ethenesulfonyl chloride</strong> (0.209 g) dropwise. The reaction mixture was warmed to room temperature and stirred for 1 hour. The mixture was diluted with dichloromethane and washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to provide the title compound. MS (ESI) m/e 471.0 (2M+H)+. | |
With triethylamine; In dichloromethane; at 0 - 20℃; for 1h; | To a solution of 6-methoxy-6-oxohexan-1-aminium chloride (0.3 g) and triethylamine (1.15 mL) in dichloromethane at 0 C. was dropwise added <strong>[6608-47-5]ethenesulfonyl chloride</strong> (0.209 g). The reaction mixture was warmed to room temperature and stirred for 1 hour. The mixture was diluted with dichloromethane and washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to provide the title compound. MS (ESI) m/e 471.0 (2M+H)+. |