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CAS No. : | 956136-85-9 | MDL No. : | MFCD16652353 |
Formula : | C22H34BNO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZDJWODLFNSRSNA-UHFFFAOYSA-N |
M.W : | 387.32 | Pubchem ID : | 53629760 |
Synonyms : |
|
Num. heavy atoms : | 28 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.68 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 117.56 |
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 : | Yes |
Log Kp (skin permeation) : | -5.59 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 4.33 |
Log Po/w (WLOGP) : | 3.72 |
Log Po/w (MLOGP) : | 2.73 |
Log Po/w (SILICOS-IT) : | 2.84 |
Consensus Log Po/w : | 2.73 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.8 |
Solubility : | 0.00617 mg/ml ; 0.0000159 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.05 |
Solubility : | 0.00343 mg/ml ; 0.00000886 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.32 |
Solubility : | 0.00185 mg/ml ; 0.00000476 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.54 |
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 |
---|---|---|
93% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; Inert atmosphere; Sealed tube | In a pressure tube a solution of tert-butyl 4-(4-bromophenyl)piperidine-1-carboxylate (1363 mg, 4.006 mmol) in dioxane was treated with bis(pinacolato)diboron (1526 mg, 6.009 mmol), KOAc (1179 mg, 12.02 mmol), and PdC12(dppf).DCM (327.1 mg, 0.4006 mmol). The mixture was sparged with nitrogen for 1 mm and then sealed and heated at 100 °C overnight. After cooling to ambient temperature, the reaction mixture was diluted with a mixture of EtOAc (75 mL)/water (50 mL)/ brine (25 mL), and the resulting emulsion was filtered through Celite® and rinsed with EtOAc. The biphasic filtrate was separated and the organic phase was washed with brine and then dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica chromatography (0-50percent EtOAc/hexanes) to afford the title compound (1437 mg, 93percent yield). ‘H NMR (CDC13) 7.76 (d, 2H), 7.22 (m, 2H), 4.24 (d, 2H), 2.79 (dt, 2H), 2.65 (tt, 1H), 1.81 (m, 2H), 1.63 (dq, 2H), 1.48 (s, 9H), 1.33 (s, 12H). |
86% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,2-dimethoxyethane at 80℃; Inert atmosphere | A mixture of tert-butyl 4- (4-bromophenyl) piperidine-1-carboxylate (510 mg, 1.499 mmol) , 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2, 2'-bi (1, 3, 2-dioxaborolane) (761 mg, 3 mmol) and KOAc (441 mg, 4.5 mmol) in DME (20 ml) was degassed with N2 and PdCl2 (dppf) -CH2Cl2 (122 mg, 0.15 mmol) was added. The resulting mixture was degassed with N2 again and was heated to 80 overnight. After cooling to rt, the mixture was added with 10mL of NH4Cl (aq) , and extracted with EtOAc (20mL × 2) . The combined organic phase was washed with brine (20mL) , dried over Na2SO4 (anhydrous) , filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (EA/Hexane 0: 100-1: 5) to give the title compound (500 mg , 86) . 1H NMR (400 MHz, CDCl3) δ ppm 1.27 (s, 9H) , 1.34 (s, 12H) , 1.57 -1.72 (m, 2H) , 1.82 (br d, J13.05 Hz, 2H) , 2.66 (br s, 1 H) , 2.80 (br t, J12.05 Hz, 2H) , 4.25 (br d, J12.80 Hz, 2H) , 7.11 -7.42 (m, 2H) , 7.77 (d, J8.03 Hz, 2H) . LC-MS: [M+H-100] + 288.2. |
3.81 g | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; Inert atmosphere | A solution of tert-butyl 4-(4-bromophenyl)piperidine-1-carboxylate (3.38 g, 11.25 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (4.57 g, 18 mmol), Pd(dppf)Cl2 (2.47 g, 3.38 mmol) and KOAc (3.32 g, 33.75 mmol) in 60 mL of DMSO, under N2, was stirred at 80° C. overnight. The volatiles were removed in vacuo, and the residue was purified by chromatography with PE/EA (40:1˜1:1) to give 3.81 g of title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59.4% | With triethylamine In 1,4-dioxane at 110℃; for 1.5 h; Inert atmosphere | Step A: Preparation of tert-butyl 4-(4-(4A5,5-tetramethyl-1 ,2-dioxaborolan-2-yl)phenyl)piperidine- 1 -carboxylate : To a solution of tert-butyl 4-(4-bromophenyl) piperidine-l-carboxylate (13.5 g, 39.7 mmol) in dioxane (40 mL) was added 4,4,5,5- tetramethyl-l,3,2-dioxaborolane (8.64 mL, 59.5 mmol) and triethylamine (16.6 mL, 119 mmol). The solution was purged with argon for 5 minutes. Dichlorobis(acetonitrile) palladium (0.309 g, 1.19 mmol) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (1.95 g, 4.76 mmol) were then added, and the reaction mixture was again purged with argon for 5 minutes. The reaction mixture was then sealed and heated at 110 °C for 90 minutes. The reaction mixture was cooled to ambient temperature and filtered through a glass fiber filter paper. The filtrate was concentrated under reduced pressure and the residue purified by silica gel column chromatography, eluting with 5-10percent EtOAc in hexanes to afford tert-butyl 4-(4- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)piperidine-l-carboxylate (9.13 g, 23.6 mmol, 59.4percent yield) as a solid. MS (apci) m/z = 288.3 (M+H-Boc). |
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