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[ CAS No. 757239-60-4 ]

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Chemical Structure| 757239-60-4
Chemical Structure| 757239-60-4
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Product Details of [ 757239-60-4 ]

CAS No. :757239-60-4 MDL No. :MFCD11110708
Formula : C13H15NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :VMBHUIMZBSWWCN-UHFFFAOYSA-N
M.W :249.26 g/mol Pubchem ID :45072502
Synonyms :

Calculated chemistry of [ 757239-60-4 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 67.91
TPSA : 55.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.73
Log Po/w (XLOGP3) : 1.25
Log Po/w (WLOGP) : 0.9
Log Po/w (MLOGP) : 1.31
Log Po/w (SILICOS-IT) : 1.3
Consensus Log Po/w : 1.5

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.02
Solubility : 2.36 mg/ml ; 0.00947 mol/l
Class : Soluble
Log S (Ali) : -2.02
Solubility : 2.38 mg/ml ; 0.00953 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.772 mg/ml ; 0.0031 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.67

Safety of [ 757239-60-4 ]

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 [ 757239-60-4 ]

* 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 [ 757239-60-4 ]
  • Downstream synthetic route of [ 757239-60-4 ]

[ 757239-60-4 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 757239-60-4 ]
  • [ 97628-92-7 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 3 h; 0076] 1-1 (4.5 g, 18.05 mmol) was dissolved in methanol (90 mL) and 2 M NaOH (27 mL, 54.2 mmol) was added.After stirring at ambient temperature for 3 hours, the solution was concentrated to be about 20 mL. 1 M HCl was addedto the resulting solution until pH reached 4 and the solution was extracted with EtOAc two times. The combined organiclayers were dried over Na2SO4 and concentrated to provide 1-2 (4.4 g, 100percent) as a white solid. MS: m/z = 236.2 (M+H).benzyl 3-(1-methyl-1H-benzimidazol-2-yl)azetidine-1-carboxylate (1-3)[0077] 1-2 (3.0 g, 12.75 mmol) was dissolved in THF (64 mL) and N-methylbenzene-1,2-diamine (2.02 g, 16.58 mmol),EDC (2.93 g, 15.30 mmol), HOAt (2.08 g, 15.30 mmol), and Hunig’s base (6.7 mL, 38.3 mmol) were added. After stirringfor 18 hours at ambient temperature, the reaction solution was concentrated. The residue was then dissolved in aceticacid (30 mL). After stirring at ambient temperature for 2 hours, the solvent was removed. The residue was partitionedbetween ethyl acetate and 5percent aqueous NaHCO3. The organic layer was dried over Na2SO4 and concentrated. Theresidue was purified by silica gel chromatography (EtOAc/Hexanes) to provide 1-3 as a off-white solid (3.32 g, 81percent).MS: m/z = 322.4 (M+H).2-(azetidin-3-yl)-1-methyl-1H-benzimidazole (Intermediate 1)[0078]
Reference: [1] Patent: WO2013/52395, 2013, A1, . Location in patent: Paragraph 38; 39
[2] Patent: EP2763672, 2016, B1, . Location in patent: Paragraph 0075; 0076
[3] Patent: WO2014/78220, 2014, A1, . Location in patent: Page/Page column 30; 31
  • 2
  • [ 100202-39-9 ]
  • [ 501-53-1 ]
  • [ 757239-60-4 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 18 h; A round bottomed flask containing methyl azetidine-3-carboxylate hydrochloride(3 g, 20 mmol), THF (30 mL) and H20 (30 mL) was added with an aqueous solution ofNaOH (4 M, 5 mL, 20 mmol) at 0 °C, followed by benzyl chloroformate (2.84 mL, 20 mmol). The reaction was vigorously stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between Et20 (100 mL) and H20 (30 mL). The aqueous phase was back-extracted withEt20 (3 x 50 mL), the combined organic phases were dried (Na2SO4) and concentrated in vacuo to give the title compound (5 g, 99percent) as a colourless oil, which was used in subsequent steps without further purification.‘H NMR (400 MHz, CDC13): ö 7.43-7.25 (m, 5 H), 5.10 (s, 2 H), 4.23-4.13 (m, 4 H), 3.74 (s, 3 H), 3.38 (q, J = 7.2 Hz, 1 H).
Reference: [1] Patent: WO2016/177849, 2016, A1, . Location in patent: Page/Page column 74; 75
[2] Patent: US2011/183960, 2011, A1, . Location in patent: Page/Page column 27
  • 3
  • [ 97628-92-7 ]
  • [ 18107-18-1 ]
  • [ 757239-60-4 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: at 0℃;
Stage #2: With acetic acid In methanol; hexanes; toluene
1-BENZYLOXYCARBONYL-3-AZETIDINECARBOXYLIC acid (from step (i); 9.3g, 39. 6MMOL) was dissolved in methanol (LOOML) and toluene (100mL), and cooled to 0°C. A solution of 2M trimethylsilyldiazomethane in hexanes was then added dropwise until bubbling had ceased and the yellow colour persisted. Acetic acid was then added dropwise until the yellow colour disappeared. Concentration of the solution yielded the title compound as an oil (9.48G, 38mmol, 96percent). IH NMR (400MHZ, CDC13) : 8 7.36-7. 31 (5H, m), 5.10 (2H, s), 4.19 (4H, D, J7. 8Hz), 3.75 (3H, s), 3.39 (1H, quintet, J 7. 8HZ).
Reference: [1] Patent: WO2004/78750, 2004, A1, . Location in patent: Page 81
  • 4
  • [ 186581-53-3 ]
  • [ 97628-92-7 ]
  • [ 757239-60-4 ]
YieldReaction ConditionsOperation in experiment
98% at 20℃; for 4 h; EXAMPLE 27B; 1-benzyl 3-methylazetidine-1,3-dicarboxylate A solution of Example 27A (4.8 g, 20.3 mmol) in ether (100 ml) was treated with diazomethane (100 ml in ether, 60 mmol) at room temperature for 4 hours. Removal of the volatiles gave Example 27B (4.8 g Yield: 98percent). MS (DCI/NH3) m/z 250 (M+H)+.
Reference: [1] Patent: US2006/229289, 2006, A1, . Location in patent: Page/Page column 19
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