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[ CAS No. 138022-04-5 ] {[proInfo.proName]}

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Chemical Structure| 138022-04-5
Chemical Structure| 138022-04-5
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Product Details of [ 138022-04-5 ]

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 :

Calculated chemistry of [ 138022-04-5 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.28

Safety of [ 138022-04-5 ]

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:

Application In Synthesis of [ 138022-04-5 ]

* 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.

  • Downstream synthetic route of [ 138022-04-5 ]

[ 138022-04-5 ] Synthesis Path-Downstream   1~10

YieldReaction ConditionsOperation 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).
  • 2
  • [ 138022-04-5 ]
  • [ 6921-22-8 ]
  • [ 1350918-33-0 ]
YieldReaction ConditionsOperation 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.
  • 3
  • [ 138022-04-5 ]
  • [ 1350918-34-1 ]
  • 4
  • [ 138022-04-5 ]
  • [ 1350918-35-2 ]
  • 5
  • [ 138022-04-5 ]
  • [ 1350916-79-8 ]
  • 6
  • [ 138022-04-5 ]
  • 4-chloropyrimidine hydrochloride [ No CAS ]
  • [ 1365155-66-3 ]
YieldReaction ConditionsOperation 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%
  • 7
  • [ 138022-04-5 ]
  • [ 1255206-70-2 ]
  • tert-butyl ({1-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperidin-4-yl}methyl)methylcarbamate [ No CAS ]
YieldReaction ConditionsOperation 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
  • 8
  • [ 138022-04-5 ]
  • [ 72486-09-0 ]
  • tert-butyl N-[(1-but-3-ynyl-4-piperidyl)methyl]-N-methylcarbamate [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 9
  • [ 138022-04-5 ]
  • 1-(2,6-dioxopiperidin-3-yl)-3-methyl-2-oxo-1,3-benzodiazole-5-carbaldehyde [ No CAS ]
  • tert-butyl N-[[1-[[1-(2,6-dioxo-3-piperidyl)-3-methyl-2-oxobenzimidazol-5-yl]methyl]-4-piperidyl]methyl]-N-methylcarbamate [ No CAS ]
YieldReaction ConditionsOperation 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)+.
  • 10
  • [ 138022-04-5 ]
  • 4-[1-(2,6-dioxo-3-piperidyl)-3-methyl-2-oxobenzimidazol-4-yl]but-3-ynyl methanesulfonate [ No CAS ]
  • tert-butyl N-[[1-[4-[1-(2,6-dioxo-3-piperidyl)-3-methyl-2-oxobenzimidazol-4-yl]but-3-ynyl]-4-piperidyl]methyl]-N-methylcarbamate [ No CAS ]
YieldReaction ConditionsOperation 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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