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[ CAS No. 343306-50-3 ] {[proInfo.proName]}

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Chemical Structure| 343306-50-3
Chemical Structure| 343306-50-3
Structure of 343306-50-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 343306-50-3 ]

CAS No. :343306-50-3 MDL No. :MFCD09909715
Formula : C16H22N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :HURFXWYAABUPFZ-UHFFFAOYSA-N
M.W : 306.36 Pubchem ID :23508726
Synonyms :

Calculated chemistry of [ 343306-50-3 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 91.05
TPSA : 70.08 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) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.64
Log Po/w (XLOGP3) : 2.36
Log Po/w (WLOGP) : 1.5
Log Po/w (MLOGP) : 0.99
Log Po/w (SILICOS-IT) : 1.41
Consensus Log Po/w : 1.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.1
Solubility : 0.244 mg/ml ; 0.000798 mol/l
Class : Soluble
Log S (Ali) : -3.47
Solubility : 0.103 mg/ml ; 0.000337 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.44
Solubility : 1.11 mg/ml ; 0.00364 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.43

Safety of [ 343306-50-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 343306-50-3 ]

* 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 [ 343306-50-3 ]
  • Downstream synthetic route of [ 343306-50-3 ]

[ 343306-50-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1761-61-1 ]
  • [ 57260-71-6 ]
  • [ 343306-50-3 ]
YieldReaction ConditionsOperation in experiment
56%
Stage #1: With sodium t-butanolate In toluene at 42℃; for 22 h; Inert atmosphere
Stage #2: With acetic acid In water; toluene for 0.166667 h;
5-(4-tert-butoxycarbonylpiperazin-1-yl)-2-hydroxybenzaldehyde
Toluene (9.7 L) was introduced into a reactor and degassed using vacuum /nitrogen.
Under nitrogen at 23°C was palladium acetate (11.0 g, 0.049 mol, 0.01 equiv.) was loaded and the mixture was stirred until complete dissolution of palladium.
A solution of tri-tert-butyl-phosphine (10.0 g, 0.049 mol, 0.01 equiv.) in toluene (0.3 L) was then added, followed by the addition of 5-bromo-2-hydroxybenzaldehyde (1000 g, 4.97 mol, 1 equiv.), tert-butyl-1-piperazinecarboxylate (1065.4 g, 5.72 mol, 1.1 equiv.) and sodium-tert-butoxide (1052.4 g, 10.9 mol, 2.2 equiv.).
The resulting yellow-orange solution was stirred for 22 h at 42°C.
The red-brownish slurry was mixed with a mixture (pH around 5-6) of distilled water (8 L) and glacial acetic acid (800 mL), and stirred for 10 min.
The organic phase was separated from the aqueous phase and washed twice with distilled water (2 x 8 L).
The organic phase was then dried by addition of sodium sulphate (2.5 kg), stirred for 30 min. and filtered.
The resulting dark-orange organic phase was weighed (9.65 kg) and an aliquot (100 g) was taken.
The aliquot was concentrated in vacuo to yield a dark-orange oil which was purified by column chromatography (SiO2, h: 30 cm, d: 4 cm, eluant: MTBE/heptane 1:1).
The named compound was obtained as yellow crystals (8.9 g).
Calculation of the total yield from the aliquot gave 56percent. MS (ES+): 307 (M+H).
Reference: [1] Patent: EP2110374, 2009, A1, . Location in patent: Page/Page column 30
[2] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 18, p. 4843 - 4852
  • 2
  • [ 50-00-0 ]
  • [ 158985-25-2 ]
  • [ 343306-50-3 ]
YieldReaction ConditionsOperation in experiment
78%
Stage #1: With tin(IV) chloride; triethylamine In dichloromethane; toluene at 20℃; for 0.5 h;
Stage #2: at 110℃;
General procedure: To a stirred suspension of 1 (20.0 mmol) in toluene(40 mL), tin tetrachloride (6.0 mmol) (1M solution in CH2Cl2) was added, followed, after 30 min, by TEA(24.0 mmol). The mixture was stirred for 30 min at rt, then paraformaldehyde (40.0 mmol) was charged.The reaction mixture was heated at 110 °C for 7/8 h, then cooled to 80 °C and treated with water (40.0mL) and AcOEt (20 mL). After stirring for 1 h the mixture was filtered through Celite, the organic layerseparated, dried (Na2SO4) and the solvent evaporated. The crude residues were purified by columnchromatography (SiO2, AcOEt/EtOH : 90/10) (2a,b) or by crystallization (2c,d).
Reference: [1] Heterocycles, 2014, vol. 88, # 1, p. 603 - 606
  • 3
  • [ 13716-12-6 ]
  • [ 1761-61-1 ]
  • [ 57260-71-6 ]
  • [ 343306-50-3 ]
YieldReaction ConditionsOperation in experiment
51% With sodium t-butanolate In n-heptane; water; toluene 1)
Synthesis of 5-(4-tert-butoxycarbonylpiperazin-1-yl)-2-hydroxybenzaldehyde
0.58 g of bis(dibenzylideneacetone)palladium and 0.16 g of tri-tert-butylphosphine are added under nitrogen to 200 ml of toluene, and the resultant solution, which becomes dark red, is stirred at 20° for 30 minutes. 10 g of 5-bromo-2-hydroxybenzaldehyde, 10.2 g of tert-butyl 1-piperazinecarboxylate and 7.2 g of sodium tert-butoxide are then added.
The mixture is stirred at 60° for 24 hours and cooled, 800 ml of water are added, and the mixture is extracted with 2*500 ml of ethyl acetate.
The organic phases are combined and washed with 300 ml of water, and the solvent is removed at 30° under reduced pressure.
The dark-orange oil which remains (11 g) is purified by chromatography (300 g of silica gel; MTB ether/heptane 5:1; 1.5 litres) leaving 7.8 g of pale-yellow crystals (51percent), m.p. 84-86°; MS 306 (M+), 250 (100percent), 233, 176, 164.
Reference: [1] Patent: US2003/125558, 2003, A1,
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