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[ CAS No. 1092522-02-5 ] {[proInfo.proName]}

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Chemical Structure| 1092522-02-5
Chemical Structure| 1092522-02-5
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Product Details of [ 1092522-02-5 ]

CAS No. :1092522-02-5 MDL No. :MFCD10693199
Formula : C12H18N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CPTVSMDBNANEBP-UHFFFAOYSA-N
M.W : 222.28 Pubchem ID :14139169
Synonyms :

Calculated chemistry of [ 1092522-02-5 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 65.99
TPSA : 55.56 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.53
Log Po/w (XLOGP3) : 1.99
Log Po/w (WLOGP) : 2.65
Log Po/w (MLOGP) : 2.07
Log Po/w (SILICOS-IT) : 0.89
Consensus Log Po/w : 2.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.727 mg/ml ; 0.00327 mol/l
Class : Soluble
Log S (Ali) : -2.78
Solubility : 0.366 mg/ml ; 0.00165 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.67
Solubility : 0.476 mg/ml ; 0.00214 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 1092522-02-5 ]

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 [ 1092522-02-5 ]

* 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 [ 1092522-02-5 ]
  • Downstream synthetic route of [ 1092522-02-5 ]

[ 1092522-02-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 474020-88-7 ]
  • [ 1092522-02-5 ]
YieldReaction ConditionsOperation in experiment
100% With iron; ammonium chloride In tetrahydrofuran; methanol; water at 50℃; for 4 h; Inert atmosphere To a solution of tert-butyl methyl(4-nitrophenyl)carbamate (8.3 g, 32.9 mmol) in THF/MeOH/H2O (150 mL/40 mL/80 mL) was added Fe powder (9.4 g, 168 mmol) and NH4Cl (18 g, 337 mmol).The reaction mixture was heated at 50° C. for 4 h under N2. After cooling to rt, the reaction mixture was filtered through a pad of Celite. The filtrate was extracted with EtOAc (100 mL*3), washed with water and brine, dried over Na2SO4, and concentrated in vacuo to afford tert-butyl 4-aminophenyl(methyl)carbamate (36) (7.3 g, yield 100percent) as a yellow solid. LC-MS (ESI): m/z (M+1) 223.
21.09 g With palladium on activated charcoal; hydrogen In isopropyl alcohol at 30℃; for 12 h; At room temperature (25 °C), 15.2g (100mmol) N-methyl-4-nitroaniline was dissolved in 75 ml isopropanol. Subsequently add 27.4 ml (200mmol) triethylamine. Stir for 15 min. Finally add 26.1g (120mmol) ditert-butyl dicarbonate. At normal temperature (25 °C), react for 3h; Subsequently add 1g Pd/C catalyst. Heat to 30 °C and perform catalytic hydrogenation. React overnight (12h); after filtering the catalyst, the solvent is removed by distillation, to obtain white transparent crystal 21.09g, the target compound, the yield is 95percent.
42 mg With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 16 h; Tert-butyl N-methyl-N-(4-aminophenyl)carbamate
To a solution of tert-butyl N-methyl-N-(4-nitrophenyl)carbamate (0.090 g, 0.356 mmol) in EtOAc (5 mL)) was added 10percent Pd/C (0.012 g) and the reaction mixture was allowed to stir under H2 atmosphere (1.5 Kg hydrogen pressure) at rt for 16 h.
The reaction mixture was filtered through a pad of Celite® and concentrated under reduced pressure to give the title compound (42 mg) as a brownish viscous oil.
Reference: [1] Patent: US2013/197014, 2013, A1, . Location in patent: Paragraph 0734; 0735
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 23, p. 10034 - 10042
[3] Patent: EP2409977, 2012, A1, . Location in patent: Page/Page column 124
[4] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 2, p. 112 - 116
[5] Patent: , 2016, , . Location in patent: Paragraph 0039; 0077; 0078; 0079
[6] Patent: US2017/174691, 2017, A1, . Location in patent: Paragraph 0776; 0777
  • 2
  • [ 24424-99-5 ]
  • [ 1092522-02-5 ]
Reference: [1] Patent: US2013/197014, 2013, A1,
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 2, p. 112 - 116
[3] Patent: , 2016, ,
  • 3
  • [ 100-15-2 ]
  • [ 1092522-02-5 ]
Reference: [1] Patent: US2013/197014, 2013, A1,
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 2, p. 112 - 116
[3] Patent: , 2016, ,
  • 4
  • [ 24424-99-5 ]
  • [ 100-15-2 ]
  • [ 1092522-02-5 ]
Reference: [1] Patent: EP2409977, 2012, A1,
  • 5
  • [ 18437-63-3 ]
  • [ 1092522-02-5 ]
Reference: [1] Patent: US2017/174691, 2017, A1,
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