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[ CAS No. 262368-47-8 ] {[proInfo.proName]}

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Chemical Structure| 262368-47-8
Chemical Structure| 262368-47-8
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Product Details of [ 262368-47-8 ]

CAS No. :262368-47-8 MDL No. :MFCD04114508
Formula : C12H18N2O Boiling Point : -
Linear Structure Formula :- InChI Key :LLPIMIMXCXEFER-UHFFFAOYSA-N
M.W : 206.28 Pubchem ID :21955025
Synonyms :

Calculated chemistry of [ 262368-47-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 65.63
TPSA : 38.49 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 1.17
Log Po/w (WLOGP) : 0.77
Log Po/w (MLOGP) : 1.13
Log Po/w (SILICOS-IT) : 1.89
Consensus Log Po/w : 1.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.95
Solubility : 2.29 mg/ml ; 0.0111 mol/l
Class : Very soluble
Log S (Ali) : -1.57
Solubility : 5.51 mg/ml ; 0.0267 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.04
Solubility : 0.188 mg/ml ; 0.000912 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.5

Safety of [ 262368-47-8 ]

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:

Application In Synthesis of [ 262368-47-8 ]

* 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 [ 262368-47-8 ]
  • Downstream synthetic route of [ 262368-47-8 ]

[ 262368-47-8 ] Synthesis Path-Upstream   1~9

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YieldReaction ConditionsOperation in experiment
100% With palladium on activated charcoal; hydrogen In methanol for 16 h; A mixture of 4-(4-nitrophenethyl)morpholine 117 (2 g, 8.46 mmol) and 500 mg of Pd/C was stirred in 100 mL of MeOH under H2 at 45 psi for 16 h. This mixture was filtered to afford 118 as a white solid (1.9 g, quant, yield). Ή NMR (300 MHz, CDC13) ppm: 6.99 (d, J= 9 Hz, 2H), 6.62 (d, J= 9 Hz, 2H), 3.73 (m, 4H), 3.60 (brs, 2H), 2.70-2.65 (m, 2H), 2.54-2.47 (m, 6H).
69% With water; iron; ammonium chloride In ethanol at 60℃; for 1 - 1.5 h; Step 3.; To a solution of 12a (1.37 g, 5.80 mmol) in ethanol (40 mL) and water (25 mL) was added iron powder (1.61 g, 29 mmol) and ammonium chloride (341 mg, 6.4 mmol) and the reaction mixture was heated at 60° C for 1.5 h. The reaction mixture was vacuum filtered through diatomaceous earth and the filtrate was concentrated. The residue was purified by chromatography (silica gel, 0-10percent methanol/methylene chloride with 1percent ammonium hydroxide) to afford 13a (820 mg, 74percent) as a bright yellow solid: 1H NMR (500 MHz, CDCI3) δ 6.98 (d, J = 8.3 Hz, 2H), 6.61 (d, J = 8.3 Hz, 2H), 3.74-3.72 (m, 4H), 3.56 (br s, 2H), 2.70-2.67 (m, 2H), 2.55-2.50 (m, 6H); ESI MS m/z 207 [C12H18N2O+ H]+.; Step 2.; To a solution of the intermediate prepared in step 1 (3.0 g, 12.7 mmol) in ethanol (80 mL) and water (40 mL) was added iron powder (3.54g, 63.5 mmol) and ammonium chloride (750mg, 14 mmol) and the reaction mixture was heated at 60° C for 1 h. The reaction mixture was vacuum filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure and purified by chromatography (silica gel, 0-10percent methanol/methylene chloride with 1percent ammonium hydroxide) to afford 15a (1.82 g, 69percent) as a bright yellow solid: 1H NMR (500 MHz, CDCI3) δ 6.98 (d, J = 8.3 Hz, 2H), 6.61 (d, J = 8.3 Hz, 2H), 3.74-3.72 (m, 4H), 3.56 (br s, 2H), 2.70- 2.67 (m, 2H), 2.55-2.50 (m, 6H); ESI MS m/z 207 [C12H18N2O+ H]+.
24.6 g With hydrogenchloride; tin(IV) chloride In water at 20℃; for 2 h; Reflux A solution of the compound (30.0 g) prepared in Reference Example P-L2 and tin chloride (96.3 g) in hydrochloric acid (100 mL) was heated under reflux for 1 hour.
After cooling, the reaction solution was stirred at room temperature for 1 hour.
CHCl3 was added thereto, and the mixture was neutralized with a saturated aqueous NaHCO3 solution.
The solution was filtered through Celite (registered trademark).
The filtrate was separated into two layers, and the aqueous layer was extracted with CHCl3.
The insoluble matter separated by Celite (registered trademark) filtration was stirred in a mixture of the aqueous layers obtained by the separation and an organic layer at room temperature for 4 hours.
The insoluble matter was removed by filtration, and the filtrate was separated into two layers.
The aqueous layer was extracted with CHCl3, and the combined organic layer was dried over MgSO4.
The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure.
The residue was dissolved in IPE (100 mL) by heating with stirring.
The solution was cooled to room temperature with stirring, followed by stirring under ice cooling for 1 hour.
The precipitated solid was collected by filtration (washed with IPE) to yield the title compound (24.6 g, orange solid).
MS (ESI pos.) m/z: 207 ([M+H]+).
387 mg With palladium 10% on activated carbon; hydrogen In methanol at 10 - 35℃; for 2.5 h; A mixture of 4-(4-nitrophenethyl)morpholine (495 mg), 10percent palladium-carbon (50 mg) and methanol (4 mL) was stirred under hydrogen atmosphere (1 atm) at room temperature for 2.5 hours.
The reaction mixture was filtered, and the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (387 mg).
1H NMR (300 MHz, CDCl3) δ 2.45-2.57 (6H, m), 2.65-2.74 (2H, m), 3.57 (2H, brs), 3.70-3.77 (4H, m), 6.59-6.65 (2H, m), 6.99 (2H, d, J=8.3 Hz).
387 mg With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 2.5 h; In a hydrogen atmosphere (1 atm), room temperature,A mixture of 4- (4-nitrophenethyl) morpholine (495 mg)10percent palladium-carbon (50 mg) and methanol (4 mL) was stirred at room temperature for 2.5 hours.The reaction mixture was filtered and dried under reduced pressure to remove the solvent from the filtrate to obtain the title compound (387 mg).

Reference: [1] Angewandte Chemie, International Edition, 2012, vol. 51, # 42, p. 10500 - 10504,5[2] Angewandte Chemie, 2012, vol. 124, # 42, p. 10652 - 10656,5
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 42, p. 10500 - 10504[4] Angew. Chem., 2012, vol. 124, # 42, p. 10652 - 10656,5
[5] Patent: WO2013/43232, 2013, A2, . Location in patent: Paragraph 00600
[6] Journal of Organic Chemistry, 2008, vol. 73, # 3, p. 1121 - 1123
[7] Patent: WO2007/18941, 2007, A2, . Location in patent: Page/Page column 85-86; 87
[8] Patent: US2004/122237, 2004, A1, . Location in patent: Page 180
[9] Patent: US2003/199478, 2003, A1,
[10] Patent: WO2007/38669, 2007, A2, . Location in patent: Page/Page column 174-175
[11] Patent: US2007/249649, 2007, A1, . Location in patent: Page/Page column 60
[12] Patent: US2007/60577, 2007, A1, . Location in patent: Page/Page column 44
[13] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 285 - 296
[14] Patent: US2013/197217, 2013, A1, . Location in patent: Paragraph 0417; 0418; 0419
[15] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 23, p. 6363 - 6369
[16] Patent: US2017/44132, 2017, A1, . Location in patent: Paragraph 0564; 0675; 0676
[17] Patent: TW2017/14883, 2017, A, . Location in patent: Paragraph 0185; 0187
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Reference: [1] Angewandte Chemie, International Edition, 2012, vol. 51, # 42, p. 10500 - 10504,5[2] Angewandte Chemie, 2012, vol. 124, # 42, p. 10652 - 10656,5
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 42, p. 10500 - 10504[4] Angew. Chem., 2012, vol. 124, # 42, p. 10652 - 10656,5
[5] Patent: WO2013/43232, 2013, A2,
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Reference: [1] Patent: WO2007/18941, 2007, A2, . Location in patent: Page/Page column 64
[2] Patent: US2013/197217, 2013, A1,
[3] Patent: US2017/44132, 2017, A1,
[4] Patent: TW2017/14883, 2017, A,
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Reference: [1] Patent: US2003/199478, 2003, A1,
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  • [ 262368-47-8 ]
Reference: [1] Patent: US2017/44132, 2017, A1,
[2] Patent: TW2017/14883, 2017, A,
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Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 285 - 296
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Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 285 - 296
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  • [ 262368-47-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 285 - 296
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  • [ 262368-47-8 ]
Reference: [1] Patent: US2013/197217, 2013, A1,
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