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[ CAS No. 265654-77-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 265654-77-1
Chemical Structure| 265654-77-1
Chemical Structure| 265654-77-1
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Product Details of [ 265654-77-1 ]

CAS No. :265654-77-1 MDL No. :MFCD01308390
Formula : C12H16N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :RZIYRKYHMDDHCK-UHFFFAOYSA-N
M.W : 236.27 Pubchem ID :419858
Synonyms :

Calculated chemistry of [ 265654-77-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 70.49
TPSA : 58.29 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.6
Log Po/w (XLOGP3) : 2.4
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 1.73
Log Po/w (SILICOS-IT) : 0.31
Consensus Log Po/w : 1.74

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.75
Solubility : 0.422 mg/ml ; 0.00179 mol/l
Class : Soluble
Log S (Ali) : -3.27
Solubility : 0.128 mg/ml ; 0.000542 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.78
Solubility : 0.392 mg/ml ; 0.00166 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 265654-77-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 265654-77-1 ]

* 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.

  • Upstream synthesis route of [ 265654-77-1 ]
  • Downstream synthetic route of [ 265654-77-1 ]

[ 265654-77-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 265654-77-1 ]
  • [ 50609-01-3 ]
YieldReaction ConditionsOperation in experiment
99.88% With hydrogen In methanol A mixture of l-[2-(4-nitrophenoxy)ethyl]pyrrolidine (from Combi-Blocks, LLC, 5.00 g, 0.0212 mol) in 100 mL of MeOH was hydrogenated in the presence of 0.5 g 10percent Pd/C, under balloon pressure of hydrogen, overnight. After filtering off the catalyst, the filtrate was evaporated to dryness and used directly in next step (4.36 g, 99.88percent). LCMS (M+H) 207.4.
99% With hydrogen In ethyl acetate at 20℃; for 3 h; Two identical reactions were set up side-by-side as follows. To a mixture of [1- [2- (4-NITRO-PHENOXY)-ETHYL]-PYRROLIDINE] (17.61 g, 74.5 mmol) and 5percent palladium on carbon (2.0 g) was added 125 mL of ethyl acetate. The reaction mixture was hydrogenated at 45 psi at room temperature for 3 hr. The mixture was filtered through diatomaceous earth under nitrogen, and the filter cake was washed with ethyl acetate and methanol. The combined filtrates from both reactions were concentrated to yield 30.46 g (99percent) of the title compound. MS 207.2 (M+1) [+]
93.71% With palladium on activated charcoal; hydrogen In methanol at 50℃; for 3 h; To a stirred suspension of Pd/C (220 mg) in methanol at 50°C was added 1-(2-(4- nitrophenoxy)ethyl) pyrrolidine (2.2 g, 0.0093 mole). Hydrogen gas was flushed into the reactionmixture for 3 hrs. The reaction mass was filtered through Celite® and washed with methanol (3x 15 ml). Filtrates were combined and evaporated under vacuum to get title compound (1.8 g,Yield: 93.71percent).LCMS: 97.52percent ESl-MS (m/z): 206.87 [M+1].
90% With palladium 10% on activated carbon; hydrogen In ethanol at 25℃; for 18 h; Under hydrogen (1 atm), to a solution of compound 9-b (1.0 g, 4.24 mmol) in ethanol (50 mL) was added 10percent Pd—C (0.5 g). The mixture was stirred at 25° C. for 18 hours, and then filtrated, the filtrate was concentrated under reduced pressure to give light yellow oil 9-a (780 mg, yield: 90percent), which was used directly for the next step without purification.

Reference: [1] Patent: WO2009/64835, 2009, A1, . Location in patent: Page/Page column 168
[2] Patent: WO2004/26823, 2004, A1, . Location in patent: Page 36
[3] Patent: WO2016/34642, 2016, A1, . Location in patent: Page/Page column 35
[4] Patent: US2015/336982, 2015, A1, . Location in patent: Paragraph 0155; 0157
[5] Journal of Organic Chemistry, 1951, vol. 16, p. 1421,1424
[6] Patent: WO2007/53452, 2007, A1, . Location in patent: Page/Page column 65
[7] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 9, p. 2527 - 2534
[8] Chemical Biology and Drug Design, 2014, vol. 83, # 5, p. 592 - 599
[9] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 5, p. 1044 - 1054
[10] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2668 - 2673
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