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[ CAS No. 135321-84-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 135321-84-5
Chemical Structure| 135321-84-5
Structure of 135321-84-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 135321-84-5 ]

CAS No. :135321-84-5 MDL No. :MFCD20261468
Formula : C14H18N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 278.30 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 135321-84-5 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 7
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 74.83
TPSA : 88.48 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.8
Log Po/w (XLOGP3) : 2.31
Log Po/w (WLOGP) : 2.32
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 1.78
Consensus Log Po/w : 2.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.78
Solubility : 0.461 mg/ml ; 0.00166 mol/l
Class : Soluble
Log S (Ali) : -3.81
Solubility : 0.0435 mg/ml ; 0.000156 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.52
Solubility : 0.0848 mg/ml ; 0.000305 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.44

Safety of [ 135321-84-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 135321-84-5 ]

* 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.

  • Upstream synthesis route of [ 135321-84-5 ]

[ 135321-84-5 ] Synthesis Path-Upstream   1~5

  • 1
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YieldReaction ConditionsOperation in experiment
77% With triethylamine In methanol at 40℃; for 5 h; Inert atmosphere Example 17: methyl 4-(N-||Y2-methyi-2- propanyf)oxy] carbonyl } carbamimidoy Dbenzo ate To a solution of methyl 4-(N-carbamimidoyl)benzoate (2.18 g, 9.18 mmol) and triethylamine (1.02 mL, 7.32 mmol) in anhydrous methanol (100 mL) was added di- tert-butyl dicarbonate (3.0 g, 13.8 mmol). The mixture was heated at 40 °C under nitrogen for 5 h. The reaction mixture was cooled and then concentrated under reduced pressure. The resulting residue was diluted with ethyl acetate (100 mL) and washed with aqueous sodium bicarbonate solution. The aqueous layer was then extracted with dichloromethane (2 x 30 mL). The combined organic extracts were dried and concentrated. Purification by flash chromatography (silica gel, 80 g, 0-30percent ethyl acetate/hexanes) afforded the title compound (1.98 g, 77percent) as a white solid. NMR (500 MHz, CDC13; Amidine NH protons were not observed.) δ 8.09 (d, 2H), 7.91 (d, 2H), 3.94 (s, 3H), 1.55 (s, 9H).
77% With triethylamine In methanol at 40℃; for 5 h; Inert atmosphere To a solution of methyl 4-(N-carbamimidoyl)benzoate (2.18 g, 9.18 mmol) and triethylamine (1.02 mL, 7.32 mmol) in anhydrous methanol (100 mL) was added di-tert-butyl dicarbonate (3.0 g, 13.8 mmol).
The mixture was heated at 40° C. under nitrogen for 5 h.
The reaction mixture was cooled and then concentrated under reduced pressure.
The resulting residue was diluted with ethyl acetate (100 mL) and washed with aqueous sodium bicarbonate solution.
The aqueous layer was then extracted with dichloromethane (2*30 mL).
The combined organic extracts were dried and concentrated.
Purification by flash chromatography (silica gel, 80 g, 0-30percent ethyl acetate/hexanes) afforded the title compound (1.98 g, 77percent) as a white solid.
1H NMR (500 MHz, CDCl3, Amidine NH protons were not observed.) δ 8.09 (d, 2H), 7.91 (d, 2H), 3.94 (s, 3H), 1.55 (s, 9H).
Reference: [1] Patent: WO2013/174937, 2013, A1, . Location in patent: Page/Page column 81
[2] Patent: US2015/152048, 2015, A1, . Location in patent: Paragraph 0487-0488
  • 2
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YieldReaction ConditionsOperation in experiment
30% With triethylamine In dichloromethane at 20℃; for 96 h; To a white suspension of Intermediate 22B (1.82 g, 7.64 mmol) in DCM (102 mL) was added di-tert-butyl dicarbonate (2.452 g, 1 1.24 mmol) and TEA (4.27 mL, 30.6 mmol). The reaction mixture was stirred at rt. Overtime, the reaction became a clear solution. After 72 h, additional di-tert-butyl dicarbonate (0.4 eq, 0.879 g) was added, and the reaction was stirred at rt. After an additional 24 h, the reaction was concentrated. Purification by normal phasechromatography afforded 0.84 g (30 percent) of Intermediate 22C as a white solid. MS (ESI) m/z: 277.3 (M-H)-. .H MR (500 MHz, CD3OD) δ ppm 1.52 (s, 9 H), 3.93 (s, 3 H), 7.86 - 7.91 (m, 2 H), 8.07 - 8.10 (m, 2 H).
Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 21, p. 7291 - 7293
[2] Patent: WO2011/100401, 2011, A1, . Location in patent: Page/Page column 150
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  • [ 24424-99-5 ]
  • [ 42823-73-4 ]
  • [ 135321-84-5 ]
Reference: [1] Patent: US5039805, 1991, A,
  • 4
  • [ 1129-35-7 ]
  • [ 135321-84-5 ]
Reference: [1] Patent: WO2011/100401, 2011, A1,
  • 5
  • [ 184778-33-4 ]
  • [ 135321-84-5 ]
Reference: [1] Patent: WO2011/100401, 2011, A1,
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