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CAS No. : | 138022-04-5 | MDL No. : | MFCD06800387 |
Formula : | C12H24N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZREUHPKGCXOWCK-UHFFFAOYSA-N |
M.W : | 228.33 | Pubchem ID : | 23004743 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.92 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 69.01 |
TPSA : | 41.57 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.68 cm/s |
Log Po/w (iLOGP) : | 2.92 |
Log Po/w (XLOGP3) : | 1.43 |
Log Po/w (WLOGP) : | 1.47 |
Log Po/w (MLOGP) : | 1.44 |
Log Po/w (SILICOS-IT) : | 1.14 |
Consensus Log Po/w : | 1.68 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.83 |
Solubility : | 3.4 mg/ml ; 0.0149 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.91 |
Solubility : | 2.82 mg/ml ; 0.0124 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.12 |
Solubility : | 1.71 mg/ml ; 0.0075 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.28 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
b) 4-(N-t-BOC-(N-methyl) aminomethyl)piperidine The above compound (0.80 g) was dissolved in 10 mL of methanol and added to 50 mL of a 5% formic acid solution in methanol which contained 375 mg of palladium black. The reaction was stirred under nitrogen for 36 hours, filtered, and concentrated. The residue was taken up in methyl acetate and extracted with 1N NaOH, brine, dried (Na2 SO4) and concentrated to give 0.59 g of the title compound as a colorless oil. 1 H NMR (CD3 OD, 300 MHz) 6 1.14 (m, 2H), 1.43 (s, 9H), 1.61 (m, 2H), 1.77 (m, 1H), 2.53 (tit, 2H), 2.82 (s, 3H), 3.03 (m, 2H), 3.12 (m, 2H). | ||
b) 4-(N-t-BOC-(N-methyl)aminomethyl) piperidine The above compound (0.80 g) was dissolved in 10 mL of methanol and added to 50 mL of a 5% formic acid solution in methanol which contained 375 mg of palladium black. The reaction was stirred under nitrogen for 36 hours, filtered, and concentrated. The residue was taken up in methyl acetate and extracted with 1N NaOH, brine, dried (Na2SO4) and concentrated to give 0.59 g of the title compound as a colorless oil. 1H NMR (CD3OD, 300 MHz) delta 1.14 (m, 2H), 1.43 (s, 9H), 1.61 (m, 2H), 1.77 (m, 1H), 2.53 (dt, 2H), 2.82 (s, 3H), 3.03 (m, 2H), 3.12 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 80℃; for 18h; | Synthesis of tert-Butyl (1~(2-fluoro-6-nitrophenyl)piperidin-4- yi)meth l(methyl)carbamate (lnt-17a)lnt-17a To a flask containing 2,3-difluoronitrobenzene (167 mg, 1.05 mmol) in CH3CN (11 mL) was added diisopropylethylamine (0.37 mL, 2.1 mmol) followed by the piperidine reagent (240 mg, 1.05 mmol). The reaction was heated at 80 C for 18 h. The solvents were removed in vacuo and the residue was purified by chromatography (ethyl acetate - hexane) to give lnt-17a (0.385 g, 99 % yield) as a bright yellow oil. LCMS m/e (M + H+) - 368.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; for 16h;Reflux; | Stage (i): tert-Butyl methyl((1-(pyrimidin-4-yl)piperidin-4-yl)methyl)carbamatetert-Butyl methyl(piperidin-4-ylmethyl)carbamate (1.4 mmol, 1.0 eq) and 4-chloropyridine (4.2 mmol, 3.0 eq) were dissolved in 2-propanol (5 ml) and DIPEA (7.0 mmol. 5.0 eq) and refluxed for 16 hours. After monitoring by TLC, the reaction solution was diluted with ethyl acetate and sat. sodium hydrogen carbonate solution and the phases were separated. The aqueous phase was washed with ethyl acetate. The combined organic phases were dried over magnesium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, ethyl acetate:ethanol 10:1+ammonia solution). Yield: 51% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 140℃; for 0.916667h;Microwave irradiation; | Step A: tert-Butyl ({l-[(2i?)-2-Hydroxy-2-(4-methyl-l-oxo-l,3-dihydro-2-benzofuran-5- yl)ethyllpiperidin-4-yl|methyl)methylcarbamate A solution of 4-methyl-5-[(2i?)-oxiran-2-yl]-2-benzofuran-l(3H)-one (76 mg, 0.40 mmol) in 2 mL of ethanol was added to <strong>[138022-04-5]tert-butyl methyl(piperidin-4-ylmethyl)carbamate</strong> (91mg, 0.40 mmol). The reaction mixture was heated at 140C in the microwave for 55 minutes. The solvents were removed in vacuo to provide tert-butyl ({l-[(2i?)-2-hydroxy-2-(4-methyl-l-oxo-l,3- dihydro-2-benzofuran-5-yl)ethyl]piperidin-4-yl}methyl)methylcarbamate which was used directly in the next step without further purification. | |
In ethanol; at 140℃; for 0.916667h;Microwave irradiation; | [0265] A solution of 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (76 mg, 0.40 mmol) in 2 mL of ethanol wasadded to <strong>[138022-04-5]tert-butyl methyl(piperidin-4-ylmethyl)carbamate</strong> (91mg, 0.40 mmol). The reaction mixture was heated at 140Cin the microwave for 55 minutes. The solvents were removed in vacuo to provide tert-butyl ({1-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperidin-4-yl}methyl)methylcarbamate which was used directly in thenext step without further purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium carbonate; In chloroform; acetonitrile; at 70℃; for 16h; | To a solution of <strong>[138022-04-5]tert-butyl N-methyl-N-(4-piperidylmethyl)carbamate</strong> (3.00 g, 13.1 mmol, CAS138200-04-5) in a mixed solvent of CHCl3 (25 mL) and ACN (25 mL) was added K2CO3 (3.63 g, 26.2 mmol) and but-3-ynyl methanesulfonate (2.53 g, 17.0 mmol, Intermediate SG). The mixture was stirred at 70 C. for 16 hours. On completion, the reaction mixture was filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography (SiO2, PE/EA=6/1) to give the title compound (2.30 g, 62% yield) as light yellow oil. 1H NMR (400 MHz, CDCl3) delta 3.09 (d, J=6.8 Hz, 2H), 2.97-2.97 (m, 2H), 2.84 (s, 3H), 2.59 (t, J=8.0 Hz, 2H), 2.45-2.32 (m, 2H), 2.04-1.93 (m, 3H), 1.65-1.55 (m, 3H), 1.45 (s, 9H), 1.30-1.20 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | To a solution of <strong>[138022-04-5]tert-butyl N-methyl-N-(4-piperidylmethyl)carbamate</strong> (119 mg, 522 umol, CAS138022-04-5) and 1-(2,6-dioxo-3-piperidyl)-3-methyl-2-oxo-benzimidazole-5-carbaldehyde (150 mg, 522 umol, Intermediate SK) in a mixed solvents of DMF (1.2 mL) and THF (2.4 mL) was added HOAc until the pH=5-6. After the reaction mixture was stirred at 10 C. for 1 hr, then NaBH(OAc)3 (221 mg, 1.04 mmol) was added. Then the reaction mixture was stirred at 10 C. for 48 hrs. On completion, the reaction mixture was quenched by H2O (0.5 mL), filtered and the filtrate was concentrated in vacuo to give a residue. The residue was purified by reverse phase (0.1% FA condition) to give the title compound (230 mg, 88% yield) as a white solid. 1H NMR (400 MHz, CDCl3) delta 8.53 (s, 1H), 7.21 (d, J=16.0 Hz, 1H), 7.01 (J=8.0 Hz, 1H), 6.76 (d, J=8.0 Hz, 1H), 5.24 (dd, J=5.2, 12.8 Hz, 1H), 4.06-3.80 (m, 2H), 3.43 (s, 3H), 3.24 (d, J=8.0 Hz, 2H), 3.13 (s, 2H), 2.98-2.87 (m, 1H), 2.87 (s, 3H), 2.79 (d, J=4.8 Hz, 1H), 2.77-2.63 (m, 1H), 2.57-2.39 (m, 1H), 2.37-2.16 (m, 2H), 1.91-1.78 (m, 1H), 1.78-1.60 (m, 2H), 1.60-1.48 (m, 1H), 1.44 (s, 9H); LC-MS (ESI+) m/z 500.4 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With potassium carbonate; In dichloromethane; acetonitrile; at 65℃; for 16h; | To a solution of 4-[1-(2,6-dioxo-3-piperidyl)-3-methyl-2-oxo-benzimidazol-4-yl]but-3-ynyl methanesulfonate (400 mg, 986 umol) and <strong>[138022-04-5]tert-butyl N-methyl-N-(4-piperidylmethyl)carbamate</strong> (270 mg, 1.18 mmol, CAS138022-04-5) in MeCN (10 mL) and CHCl3 (10 mL) was added K2CO3 (409 mg, 2.96 mmol). The reaction mixture was stirred at 65 C. for 16 hrs. On completion, the reaction mixture was diluted with water (30 mL) and extracted with EA (3×50 mL). The combined organic layers was dried over Na2SO4, filtered and concentrated in vacuo to give a residue. The residue was purified by reverse phase (0.1% FA condition) to give the title compound (140 mg, 26% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 11.11 (s, 1H), 7.11 (d, J=7.2 Hz, 1H), 7.07-7.02 (m, 1H), 7.01-6.96 (m, 1H), 5.38 (dd, J=5.2, 12.8 Hz, 1H), 3.67 (s, 3H), 3.05 (d, J=6.4 Hz, 2H), 2.96-2.87 (m, 3H), 2.69-2.58 (m, 9H), 2.05-1.94 (m, 3H), 1.58-1.51 (m, 3H), 1.38 (s, 9H), 1.18-1.08 (m, 2H); LC-MS (ESI+) m/z 538.4 (M+H)+. |
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