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[ CAS No. 192189-16-5 ] {[proInfo.proName]}

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Chemical Structure| 192189-16-5
Chemical Structure| 192189-16-5
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Product Details of [ 192189-16-5 ]

CAS No. :192189-16-5 MDL No. :MFCD16877631
Formula : C12H13BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CDJLRWSJPXZDKY-UHFFFAOYSA-N
M.W : 297.15 Pubchem ID :57415820
Synonyms :

Calculated chemistry of [ 192189-16-5 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 69.64
TPSA : 44.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.87
Log Po/w (XLOGP3) : 2.89
Log Po/w (WLOGP) : 3.58
Log Po/w (MLOGP) : 2.18
Log Po/w (SILICOS-IT) : 2.2
Consensus Log Po/w : 2.74

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.7
Solubility : 0.0597 mg/ml ; 0.000201 mol/l
Class : Soluble
Log S (Ali) : -3.48
Solubility : 0.0992 mg/ml ; 0.000334 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.83
Solubility : 0.0442 mg/ml ; 0.000149 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.25

Safety of [ 192189-16-5 ]

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 [ 192189-16-5 ]

* 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 [ 192189-16-5 ]
  • Downstream synthetic route of [ 192189-16-5 ]

[ 192189-16-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 24424-99-5 ]
  • [ 23612-36-4 ]
  • [ 192189-16-5 ]
YieldReaction ConditionsOperation in experiment
97% With dmap In tetrahydrofuran at 17 - 20℃; N-BOC-3-bromo-5-azaindole[00146] Referring now to the Scheme 1 as shown in Fig. 1 , a solution of 3.5601g(18.06 mmol) of 3-bromo-5-azaindole (2) and 0.4651 g (3.8 mmol, 21 molpercent) of dimethylaminopyridine (DMAP) in 80 ml. of THF was placed in a 250 ml. three-neck round-bottom flask equipped with a magnetic stirrer, thermocouple, nitrogen bleed, and cooling ice bath. A total of 4.7769g (21.88 mmol, 1.2 eq.) of BOC2O was added to the flask at 17°C, and the resulting mixture was stirred until starting 3-bromo-5-azaindole disappeared, as monitored by TLC (generally, overnight stirring at room temperature). The resulting yellow solution was concentrated on rotavap, washed with 100 ml. of saturated sodium bicarbonate, and extracted with dichloromethane (3x80 ml_). The organic phase was dried over Na2SO4 and concentrated on rotavap to afford 6.57g of orange solid. This crude material was purified on CombiFlash using hexane/ethyl acetate as eluent to give 5.25g (97percent yield) of n-boc-3-bromo-5-azaindole (3) as a white solid.
90% With dmap In dichloromethane for 1.33333 h; To a mixture of Intermediate 1 (1.80 g, 9.14 mmol) in DCM (60 mL) was added di-tert- butyl dicarbonate (2.18 g, 10.0 mmol) followed by 4-dimethylaminopyridine (122 mg, 1.00 mmol). After 80 min the solution was diluted with DCM (20 mL) and washed with 0.1 M HC1 (25, 10 mL) and brine. The organic layer was dried (Na2S04), filtered and evaporated to yield the title compound as a light yellow solid (2.47 g, 90percent). MS (ESI+) m/z = 299 (M+H)+.
90% With dmap In dichloromethane at 20℃; for 1.33333 h; To a mixture of Intermediate 1 (1.80 g, 9.14 mmol) in DCM (60 mL) was added di-tert-butyl dicarbonate (2.18 g, 10.0 mmol) followed by 4-dimethylaminopyridine (122 mg, 1.00 mmol).
After 80 min the solution was diluted with DCM (20 mL) and washed with 0.1 M HCl (25, 10 mL) and brine.
The organic layer was dried (Na2SO4), filtered and evaporated to yield the title compound as a light yellow solid (2.47 g, 90percent). MS (ESI+) m/z=299 (M+H)+.
Reference: [1] Patent: WO2010/33981, 2010, A2, . Location in patent: Page/Page column 28
[2] Patent: WO2011/113798, 2011, A2, . Location in patent: Page/Page column 35
[3] Patent: US2013/102587, 2013, A1, . Location in patent: Paragraph 0183; 0184
[4] Journal of Medicinal Chemistry, 1997, vol. 40, # 15, p. 2430 - 2433
  • 2
  • [ 271-34-1 ]
  • [ 192189-16-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 15, p. 2430 - 2433
[2] Patent: WO2011/113798, 2011, A2,
[3] Patent: US2013/102587, 2013, A1,
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