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CAS No. : | 286961-15-7 | MDL No. : | MFCD11521562 |
Formula : | C19H26BNO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QDSFHRPYZPQWEJ-UHFFFAOYSA-N |
M.W : | 343.23 | Pubchem ID : | 11290836 |
Synonyms : |
|
Num. heavy atoms : | 25 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.53 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 101.93 |
TPSA : | 48.0 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.37 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.85 |
Log Po/w (WLOGP) : | 3.05 |
Log Po/w (MLOGP) : | 1.98 |
Log Po/w (SILICOS-IT) : | 1.84 |
Consensus Log Po/w : | 1.95 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.61 |
Solubility : | 0.084 mg/ml ; 0.000245 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.52 |
Solubility : | 0.104 mg/ml ; 0.000304 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.53 |
Solubility : | 0.0101 mg/ml ; 0.0000294 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.95 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
78% | With potassium acetate In 1,4-dioxane at 80℃; for 16 h; | [1245] The title compound was prepared according to the procedure described in Tetrahedron Lett. 2000, 41 3705. Bis(pinacolato)diborane (338 mg, 1.33 mmol), potassium acetate (356 mg, 3.63 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2dppf; 30 mg, 0.04 mmol), and 1,1'-bis(diphenylphosphino)ferrocene (20 mg, 0.04 mmol) were combined and treated with the product from Example 58A (440 mg, 1.21 mmol) in degassed 1,4-dioxane (7 mL). The reaction mixture was heated at 80° C. for 16 hours, allowed to cool to 23° C., diluted with water, and extracted with dichloromethane (3.x.). The dichloromethane extracts were combined, dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was chromatographed on flash silica gel (20percent ethyl acetate:hexanes) to provide the title compound (323 mg, 78percent yield). 1H NMR (300 MHz, CDCl3) δ1.25 (s, 12H), 2.24 (m, 2H), 3.52 (dd, 2H, J=5.7, 5.7 Hz), 4.03 (dd, 2H, J=6 Hz), 5.14 (s, 2H), 6.46 (br m, 1H), 7.32 (m, 5H); MS (ESI) m/e 344 (M+H)+. |
78% | With potassium acetate In 1,4-dioxane at 80℃; for 16 h; | The title compound was prepared according to the procedure described in Tetrahedron Lett. 2000, 41 3705. Bis(pinacolato)diborane (338 mg, 1.33 mmol), potassium acetate (356 mg, 3.63 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2dppf; 30 mg, 0.04 mmol), and 1,1'-bis(diphenylphosphino)ferrocene (20 mg, 0.04 mmol) were combined and treated with the product from Example 58A (440 mg, 1.21 mmol) in degassed 1,4-dioxane (7 mL). The reaction mixture was heated at 80 C. for 16 hours, allowed to cool to 23 C., diluted with water, and extracted with dichloromethane (3). The dichloromethane extracts were combined, dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was chromatographed on flash silica gel (20percent ethyl acetate:hexanes) to provide the title compound (323 mg, 78percent yield). 1H NMR (300 MHz, CDCl3) ? 1.25 (s, 12H), 2.24 (m, 2H), 3.52 (dd, 2H, J=5.7, 5.7 Hz), 4.03 (dd, 2H, J=3, 6 Hz), 5.14 (s, 2H), 6.46 (br m, 1H), 7.32 (m, 5H); MS (ESI) m/e 344 (M+H)+. |
43.8% | With potassium acetate In 1,4-dioxane at 90℃; for 16 h; | Step 2 benzyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)- carboxylate (173); [0356] A mixture of bis(pinacolato)diboron (3 14 g, 12 38 mmol), 172 (5 26 g, 12 38 mmol),DPPF (0 206 g, 0 371 mmol), PdCI2(dppf)-CH2CI2 adduct (0 303 g, 0 371 mmol) and potassium acetate (2 430 g, 24 76 mmol) was heated at 90 0C in 1 ,4-dioxane (60 mL) for 16 hours It was then diluted with water (200ml) and extracted with ethyl acetate (3x), dried overNa2SO4, filtered and then purified by silica gel chromatography (Flash, 20Og silica and 10 to20percent ethyl acetate in hexanes) to give 173 (1 86 g, 5 42 mmol, 43 8 percent yield) LRMS (E-Sl)(calc ) 343 2 (found) 344 3 (MH)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine In dichloromethane at 20℃; for 2 h; | Example 2: Tetrahydropyridine 2 was prepared in 3 steps starting with the deprotection of 1 using Method 3. The resulting HCl amine salt was dissolved in dichloromethane (0.2 M). Benzyl chloroformate (1.2 equiv) was added followed by triethylamine (3.0 equiv). The reaction was allowed to stir at room temperature for 2h after which point it was diluted with IN HCl and extracted with excess dichloromethane. The organic layer was dried over MgSψ4 and concentrated to provide the desired carbamate in quantitative yield, which was converted directly to boronic acid 2 using Method 2. [M-H]- = 260.1 m/z. Activity: B |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: With TurboGrignard In 2-methyltetrahydrofuran at -15 - -10℃; Stage #2: at 20℃; |
2nd step: under the protection of nitrogen, the 1M isopropyl magnesium chloride-lithium chloride (88 ml, 88mmol) into the reaction bottle, temperature control -15 ° C to -10 °C, dropwise N-Cbz-1, 2, 5, 6-tetrahydro-pyridine-4-bromo, 2-methyl tetrahydrofuran (90 ml) solution, stirring finishing joining 1-2 hours. After the end of the exchange, then drop by adding methoxy boronic acid pinacone ester (14.2g, 90mmol), subsequently maintain the reaction at room temperature overnight. Adding 10percent hydrochloric acid aqueous solution quenching reaction, adjusting PH= 4-5, adding 220 ml ethyl acetate, saturated salt water an organic layer, the organic layer after evaporation to dryness, add ethanol/heptane 10:1 obtained after pulping 19.2g a buff solid N-Cbz-1, 2, 5, 6-tetrahydro-pyridine-4-boronic acid frequency that alcohol ester, GC: 99.6percent, yield: 56percent. |
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