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[ CAS No. 283173-50-2 ] {[proInfo.proName]}

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Chemical Structure| 283173-50-2
Chemical Structure| 283173-50-2
Structure of 283173-50-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 283173-50-2 ]

CAS No. :283173-50-2 MDL No. :
Formula : C19H18FN3O Boiling Point : -
Linear Structure Formula :- InChI Key :HMABYWSNWIZPAG-UHFFFAOYSA-N
M.W : 323.36 Pubchem ID :9931954
Synonyms :
AG014699;PF-01367338;AG-014447

Calculated chemistry of [ 283173-50-2 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.21
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 96.03
TPSA : 56.92 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.48
Log Po/w (XLOGP3) : 2.49
Log Po/w (WLOGP) : 2.87
Log Po/w (MLOGP) : 2.6
Log Po/w (SILICOS-IT) : 4.65
Consensus Log Po/w : 3.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.68
Solubility : 0.0679 mg/ml ; 0.00021 mol/l
Class : Soluble
Log S (Ali) : -3.33
Solubility : 0.151 mg/ml ; 0.000467 mol/l
Class : Soluble
Log S (SILICOS-IT) : -7.67
Solubility : 0.0000069 mg/ml ; 0.0000000213 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.81

Safety of [ 283173-50-2 ]

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 [ 283173-50-2 ]

* 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 [ 283173-50-2 ]
  • Downstream synthetic route of [ 283173-50-2 ]

[ 283173-50-2 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 880160-69-0 ]
  • [ 283173-50-2 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: at 20℃; for 46 h;
Stage #2: With sodium hydroxide In water at 0 - 35℃;
Example 13
Synthesis of 8-Fluoro-2-(4-methylaminomethyl-phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one (15)
Lactam 14 (14.42 g, 0.038 mol) was dissolved in hydrobromic acid in acetic acid (30percent-32percent, 140 ml).
The reaction solution was stirred for 46 hours at room temperature in a 500 ml flask that was connected to an ethanolamine scrubber system. HPLC analysis indicated the completion of the reaction.
Ice (30 g) was added to the reaction solution followed by addition of aqueous NaOH (327 ml, 10 M, 3.27 mol) while the temperature was maintained between 25° C. and 35° C.
When addition of NaOH was complete, the pH was 10.
The resulting solid was collected by filtration, washed with water (2*50 ml).
The filter cake was then suspended in water (125 ml) and stirred for 2 hours.
The solid was collected by filtration, washed with water (2*25 ml) and dried to afford 10.76 g of product (88percent yield).
1H NMR (300 MHz, DMSO-d6) δ 2.577(s, 3H), 3.053(m, 2H), 3.406(m, 2H), 4.159(s, 2H), 7.36(dd, 1H, J=2.4 Hz and J=9.3 Hz), 7.44(dd, 1H, J=2.4 Hz and J=11.1 Hz), 7.63(d, 2H, J=8.1 Hz), 7.70(d, 2H, J=8.1 Hz), 8.265(t, 1H, J=5.7 Hz), 11.77(s, 1H).
Exact mass calculated for C19H19FN3O: 324.1512. Found: 324.1497.
Reference: [1] Patent: US2006/63926, 2006, A1, . Location in patent: Page/Page column 6; 11
  • 2
  • [ 283173-80-8 ]
  • [ 518336-26-0 ]
  • [ 283173-50-2 ]
YieldReaction ConditionsOperation in experiment
6.82 g With bis(acetato)bis(triphenylphosphine)palladium(0); sodium carbonate In methanol; water at 60℃; for 4 h; Inert atmosphere 2-Bromo-8-fluoro-4,5-dihydro-lH-azepino[5,4,3-cd]indol-6(3H)-one (10 g; 35.3 mmol), prepared according to process described in Example 3, sodium carbonate (3.74 g; 35.3 mmol), bis(triphenylphosphine)palladium(II) diacetate (0.529 g; 0.71 mmol) and (4-((methylamino)methyl)phenyl)boronic acid solution (75 ml; 45.9 mmol), prepared according to process described in Example 2, are charged into a three-necked round bottom flask, followed by inertisation with nitrogen. A previously degassed mixture of methanol (130 mL) and water (40 mL) is added and the reaction mixture is stirred at 60°C for 4 hours. The reaction mixture is cooled to ambient temperature followed by addition of activated carbon. The mixture is stirred at ambient temperature for one hour, heated to 50 °C, stirred for another hour and then filtered through a layer of celite. The solution of 8-fluoro-2-(4- ((methylamino)methyl)phenyl)-4,5-dihydro-lH-azepino[5,4,3-cd]indol-6(3H)-one is concentrated to about 110 mL, heated to 40°C followed by dropwise addition of water (40 mL). Reaction mixture is cooled to ambient temperature and stirred for 17 hours at ambient temperature and additional one hour at 0-5°C. Solid is filtered off, washed with water and dried in vacuum oven at 50°C for 5 hours. Crude material (9.5 g) is suspended in methanol (95mL) at reflux temperature and stirred for 20 minutes. Suspension is than cooled down and stirred for 17 hours at ambient temperature and 1.5 hour at 0-5°C. Crystals are filtered off, washed with methanol and dried in vacuum oven at 50°C for 4 hours to obtain 6.82 g of Rucaparib base.
Reference: [1] Patent: WO2018/140377, 2018, A1, . Location in patent: Paragraph 00325; 00327
  • 3
  • [ 283173-84-2 ]
  • [ 74-89-5 ]
  • [ 283173-50-2 ]
Reference: [1] ACS Chemical Neuroscience, 2018, vol. 9, # 6, p. 1259 - 1263
  • 4
  • [ 773059-19-1 ]
  • [ 283173-50-2 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1897 - 1904
  • 5
  • [ 283173-84-2 ]
  • [ 283172-68-9 ]
  • [ 283173-50-2 ]
Reference: [1] Patent: US6495541, 2002, B1,
  • 6
  • [ 1408282-26-7 ]
  • [ 283173-50-2 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1897 - 1904
[2] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1897 - 1904
[3] ACS Chemical Neuroscience, 2018, vol. 9, # 6, p. 1259 - 1263
[4] Patent: WO2018/140377, 2018, A1,
  • 7
  • [ 283173-80-8 ]
  • [ 283173-50-2 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1897 - 1904
[2] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1897 - 1904
[3] ACS Chemical Neuroscience, 2018, vol. 9, # 6, p. 1259 - 1263
  • 8
  • [ 399-51-9 ]
  • [ 283173-50-2 ]
Reference: [1] ACS Chemical Neuroscience, 2018, vol. 9, # 6, p. 1259 - 1263
  • 9
  • [ 141071-78-5 ]
  • [ 283173-50-2 ]
Reference: [1] ACS Chemical Neuroscience, 2018, vol. 9, # 6, p. 1259 - 1263
  • 10
  • [ 283173-84-2 ]
  • [ 283173-50-2 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1897 - 1904
[2] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1897 - 1904
  • 11
  • [ 1408282-25-6 ]
  • [ 283173-50-2 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1897 - 1904
[2] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1897 - 1904
  • 12
  • [ 87199-17-5 ]
  • [ 283173-50-2 ]
Reference: [1] Patent: WO2018/140377, 2018, A1,
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[ 283173-50-2 ]

Chemical Structure| 459868-92-9

A424427[ 459868-92-9 ]

8-Fluoro-2-(4-((methylamino)methyl)phenyl)-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-one phosphate

Reason: Free-salt