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CAS No. : | 167263-04-9 | MDL No. : | MFCD11227109 |
Formula : | C16H21N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OUILGYJQVAMETA-UHFFFAOYSA-N |
M.W : | 287.36 | Pubchem ID : | 53439111 |
Synonyms : |
|
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.56 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 83.31 |
TPSA : | 66.22 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.8 cm/s |
Log Po/w (iLOGP) : | 2.81 |
Log Po/w (XLOGP3) : | 1.77 |
Log Po/w (WLOGP) : | 2.49 |
Log Po/w (MLOGP) : | 1.27 |
Log Po/w (SILICOS-IT) : | 2.23 |
Consensus Log Po/w : | 2.11 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.68 |
Solubility : | 0.595 mg/ml ; 0.00207 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.78 |
Solubility : | 0.478 mg/ml ; 0.00167 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.72 |
Solubility : | 0.055 mg/ml ; 0.000191 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.39 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
44% | With sodium hydride In DMF (N,N-dimethyl-formamide); oil at 0 - 60℃; for 5.63333 h; | Sodium hydride (60percent in mineral oil, 2.04g, 51mmol) was added portion wise over 8 minutes to a stirring solution of 2-pyridineacetonitrile (1. 8ml, 17mmol) and N- (tert-butyloxycarbonyl) bis (2-chloroethyl) amine in anhydrous DMF (50ml) at 0OC. The reaction was then heated at 60°C for 5 1/2hours. The reaction was cooled and extracted into ethyl acetate (4 x 150ml), and washed with water (3 x 200ml). The organic layer was then dried over anhydrous MgSO.cents., filtered and evaporated in vacuo to give a red/black oil. This was absorbed onto silica and purified by column chromatography using 20percent ethyl acetate in isohexane to give ter-butyl 4-cyano-4-pyridin-2-ylpiperidine-1-carboxylate as an orange solid (2.13g, 44percent). 1H NMR 8 (ppm) 360MHz (CDC13): 1.48 (9 H, s), 2.04-2. 08 (2 H, m), 2.17-2. 25 (2 H, m), 3.15-3. 28 (2 H, m), 4.20-4. 35 (2 H, m), 7.25-7. 29 (1 H, m), 7.61 (1 H, d, J = 8Hz), 7.73-7. 78 (1 H, m), 8. 61 (1 H, dd, J = 0.7, 3.9Hz). MSp m/z for MH+ = 287 (- 56). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4 g | With lithium hexamethyldisilazane In tetrahydrofuran at 18 - 25℃; for 1.5 h; | To a solution of 1-(tert-butoxycarbonyl)-4-cyano-2,3,4,5-tetrahydropyridin-1-ium (3.24 g, 15.43 mmol) and2-fluoropyridine (1.65 g, 16.97 mmol) in THF (20 mL) at RTwas added LHMDS (18.5 mL, 18.5 mmol, 1 M in THFsolution). The reaction mixture was stirred at RT for 1.5 h.Upon completion of the reaction, the reaction mixture wasquenched with water (50 mL) and extracted with EtOAc (50mLx3). The combined organic phase was dried over anhydrousNa2S04 and concentrated under reduced pressure. Theresidue was purified by silica-gel column chromatography toafford 4 g of tert-butyl 4-cyano-4-(pyridin-2-yl)piperidine-1-carboxylate. LC-MS (ESI+): m/z 288 [M+Ht. |
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