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[ CAS No. 1201923-48-9 ] {[proInfo.proName]}

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Chemical Structure| 1201923-48-9
Chemical Structure| 1201923-48-9
Structure of 1201923-48-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1201923-48-9 ]

CAS No. :1201923-48-9 MDL No. :MFCD28359281
Formula : C22H23FN2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :TWQAEDUMDUDFGX-INIZCTEOSA-N
M.W : 398.43 Pubchem ID :58282788
Synonyms :

Calculated chemistry of [ 1201923-48-9 ]

Physicochemical Properties

Num. heavy atoms : 29
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.32
Num. rotatable bonds : 8
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 109.33
TPSA : 75.71 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.35
Log Po/w (XLOGP3) : 3.72
Log Po/w (WLOGP) : 3.6
Log Po/w (MLOGP) : 3.24
Log Po/w (SILICOS-IT) : 3.79
Consensus Log Po/w : 3.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.43
Solubility : 0.0147 mg/ml ; 0.000037 mol/l
Class : Moderately soluble
Log S (Ali) : -5.0
Solubility : 0.00397 mg/ml ; 0.00000997 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.59
Solubility : 0.000102 mg/ml ; 0.000000256 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.34

Safety of [ 1201923-48-9 ]

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 [ 1201923-48-9 ]

* 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 [ 1201923-48-9 ]
  • Downstream synthetic route of [ 1201923-48-9 ]

[ 1201923-48-9 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 1201923-48-9 ]
  • [ 1047644-62-1 ]
Reference: [1] Drugs of the Future, 2014, vol. 39, # 8, p. 541 - 546
  • 2
  • [ 136918-14-4 ]
  • [ 944470-56-8 ]
  • [ 1201923-48-9 ]
Reference: [1] Patent: WO2009/158371, 2009, A1, . Location in patent: Page/Page column 33; 34
[2] Patent: WO2009/158372, 2009, A1, . Location in patent: Page/Page column 30
[3] Patent: US2013/96144, 2013, A1, . Location in patent: Paragraph 0248-0250
[4] Drugs of the Future, 2014, vol. 39, # 8, p. 541 - 546
[5] Patent: WO2009/158374, 2009, A2, . Location in patent: Page/Page column 29; 30
  • 3
  • [ 136918-14-4 ]
  • [ 1201923-48-9 ]
YieldReaction ConditionsOperation in experiment
67.2% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 0.5 h; Cooling with ice To an ice cooled mixture of [(S)-2-(3-fluoro-phenyl)-1-hydroxymethyl-ethyl]carbamic acid tert-butyl ester (1.214 g, 4.5 mmol), triphenyl phosphine (1.359 g, 5.18 mmol), phthalimide (0.762 g, 5.18 mmol) and tetrahydrofuran (15 mL) was added a solution of diisopropyldiazodicarboxylate (1.048 g, 5.18 mmol) in tetrahydrofuran (5 mL). The mixture was stirred for 30 minutes at room temperature and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with dichloromethane-ethyl acetate (90:10) to give [(S)-1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(3-fluoro-phenyl)-ethyl]carbamic acid tert-butyl ester as a white solid. (Yield 1.205 g, 67.2percent).
Reference: [1] Patent: US2012/184542, 2012, A1, . Location in patent: Page/Page column 106
  • 4
  • [ 114873-01-7 ]
  • [ 1201923-48-9 ]
Reference: [1] Drugs of the Future, 2014, vol. 39, # 8, p. 541 - 546
[2] Patent: US2013/96144, 2013, A1,
[3] Patent: WO2009/158371, 2009, A1,
[4] Patent: WO2009/158372, 2009, A1,
[5] Patent: WO2009/158374, 2009, A2,
  • 5
  • [ 1201923-48-9 ]
  • [ 1202237-87-3 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 12 h; To a solution of 1 ,1-dimethylethyl 1 ,1-dimethylethyl {(1 S)-2-(1 ,3-dioxo-1 ,3-dihydro-2/-/-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate (9.0 g, 22.6 mmol) in DCM (200 ml.) at RT was added 4M HCI in dioxane (56 ml_, 226 mmoles). After 12h, the solution was filtered and washed with DCM (50 ml.) affording the title compound (7.8 g,99percent) as a white HCI salt: LCMS (ES) m/z 349 (M+H)+.
99% With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 12 h; To a solution of 1 ,1-dimethylethyl 1 ,1-dimethylethyl {(1 S)-2-(1 ,3-dioxo-1 ,3-dihydro- 2/-/-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate (9.0 g, 22.6 mmol) in DCM (200 mL) at RT was added 4M HCI in dioxane (56 mL, 226 mmoles). After 12h, the solution was filtered and washed with DCM (50 mL) affording the title compound (7.8 g, 99percent) as a white HCI salt: LCMS (ES) m/z 349 (M+H)+.
3.1 g With hydrogenchloride In 1,4-dioxane; methanol at 20℃; for 2 h; Step B
2-[(2S)-2-amino-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione [1.0]-hydrogen chloride
To a solution of tert-butyl[(1S)-1-(3-fluorobenzyl)-2-hydroxyethyl]carbamate (9.40 g, 34.9 mmol), triphenylphosphine (9.15 g, 34.9 mmol), and phthalimide (5.14 g, 34.9 mmol) in tetrahydrofuran (100 mL, 1000 mmol) at room temperature was added diethyl azodicarboxylate (17.9 mL, 45.4 mmol).
The reaction was stirred at room temperature for 2 hr and then concentrated under reduced pressure.
The residue was purified by combi-flash chromatography eluted with EtOAc/hexane (0-40percent) to give the desired intermediate. LCMS found: 399.0 (M+1).
To the solution of the purified intermediate in methanol (20 mL, 400 mmol) was added 4.0 M hydrogen chloride in dioxane (30 mL, 100 mmol).
The mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure to give 3.1 g (26percent total yield for the two steps) of the final product, 2-[(2S)-2-amino-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione [1.0]-Hydrogen chloride, as white solid. LC/MS found: 299.0 (M+H)+.
Reference: [1] Patent: WO2009/158371, 2009, A1, . Location in patent: Page/Page column 34
[2] Patent: WO2009/158372, 2009, A1, . Location in patent: Page/Page column 30
[3] Patent: US2013/96144, 2013, A1, . Location in patent: Paragraph 0248-0250
[4] Patent: WO2009/158374, 2009, A2, . Location in patent: Page/Page column 30
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