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[ CAS No. 395101-67-4 ] {[proInfo.proName]}

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Chemical Structure| 395101-67-4
Chemical Structure| 395101-67-4
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Product Details of [ 395101-67-4 ]

CAS No. :395101-67-4 MDL No. :MFCD09263218
Formula : C8H4BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :WVHZCDQLDZQYPH-UHFFFAOYSA-N
M.W :222.04 Pubchem ID :22260847
Synonyms :

Calculated chemistry of [ 395101-67-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.51
TPSA : 52.47 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) : -6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.25
Log Po/w (XLOGP3) : 2.3
Log Po/w (WLOGP) : 2.2
Log Po/w (MLOGP) : 1.5
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 1.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.22
Solubility : 0.134 mg/ml ; 0.000602 mol/l
Class : Soluble
Log S (Ali) : -3.04
Solubility : 0.203 mg/ml ; 0.000912 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.86
Solubility : 0.0309 mg/ml ; 0.000139 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 395101-67-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 395101-67-4 ]

* 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 [ 395101-67-4 ]
  • Downstream synthetic route of [ 395101-67-4 ]

[ 395101-67-4 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 74626-47-4 ]
  • [ 395101-67-4 ]
YieldReaction ConditionsOperation in experiment
93% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 2 h;   1H-Indazole-5-carbonitrile (90 mg, 0.62 mmol) was dissolved in dry   DMF (1 mL) and   N-bromosuccinimide (134 mg, 0.75 mmol) was added at room temperature and stirred at this temperature for 2 hours. After removal of the solvent under vacuum, the residue was treated with   ethyl acetate, washed successively with saturated aqueous solution of   sodium hydrogen carbonate,   water and brine. The organic extracts were dried over anhydrous sodium sulphate and the solvent was removed under vacuum to afford the   title compound (128 mg, 93percent). LRMS (m/z): 222/224 (Br).
89% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 2 h; Inert atmosphere 1H-indazole-5-carbonitrile (544 mg, 3.8 mmol), NBS (812 mg, 4.6 mmol) and DMF (10 mL) were added in a 100 mL of round-bottom flask. Under the protection of N2, the mixture was stirred at room temperature for 2 h. The reaction solution was concentrated to obtain a crude product which was dissolved in 100 mL of DCM, washed with 50 mL of saturated sodium bicarbonate aqueous solution, water and saturated brine respectively. The organic phase was dried over anhydrous sodium sulfate, and filtered. The resulting filtrate was concentrated to obtain 3-bromo-1H-indazole-5-carbonitrile (750 mg, 89percent).
47% With hydrogenchloride; bromine In methanol; aq. NaOH; water; ethyl acetate B.
3-Bromo-1H-Indazole-5-Carbonitrile
A 2-L round bottomed flask was charged with 1H-indazole-5-carbonitrile (17.6 g, 123 mmol), 333 mL methanol (MeOH), 333 mL of 2.0 M aq. NaOH, and a solution of bromine (Br2, 54.7 g, 344 mmol, 2.80 equiv.) in 166 mL of 2.0 M aq. NaOH.
The mixture was warmed on an oil bath to 40° C. (external temperature) for 6 h, and then cooled to room temperature in a water bath.
The pH of the solution adjusted to ca. 5.5 with 103 mL of 4.0 M aq. HCl.
The resulting precipitate was collected by filtration, washed with 200 mL of H2O, and dried.
The product was purified by chromatography on 265 g of silica gel using 30-40percent EtOAc in hexanes.
This afforded the title compound (12.83 g, 47percent yield): ES-MS (m/z) 222 [M+1]+.
47% With hydrogenchloride; bromine In methanol; aq. NaOH; water; ethyl acetate B.
3-Bromo-1H-indazole-5-carbonitrile
A 2-L round bottomed flask was charged with 1H-indazole-5-carbonitrile (17.6 g, 123 mmol), 333 mL methanol (MeOH), 333 mL of 2.0 M aq. NaOH, and a solution of bromine (Br2, 54.7 g, 344 mmol, 2.80 equiv.) in 166 mL of 2.0 M aq. NaOH.
The mixture was warmed on an oil bath to 40° C. (external temperature) for 6 h, and then cooled to room temperature in a water bath.
The pH of the solution adjusted to ca. 5.5 with 103 mL of 4.0 M aq. HCl.
The resulting precipitate was collected by filtration, washed with 200 mL of H2O, and dried.
The product was purified by chromatography on 265 g of silica gel using 30-40percent EtOAc in hexanes.
This afforded the title compound (12.83 g, 47percent yield): ES-MS (m/z) 222 [M+1]+.

Reference: [1] Patent: EP2489663, 2012, A1, . Location in patent: Paragraph 0215; 0216
[2] Patent: EP3205650, 2017, A1, . Location in patent: Paragraph 0616; 0617
[3] Patent: US2002/103229, 2002, A1,
[4] Patent: US2004/127536, 2004, A1,
[5] Patent: US2005/9876, 2005, A1,
[6] Patent: US2002/103229, 2002, A1,
[7] Patent: US2004/127536, 2004, A1,
[8] Patent: US2005/9876, 2005, A1,
[9] Patent: EP1380576, 2004, A1, . Location in patent: Page 54-55
  • 2
  • [ 146137-79-3 ]
  • [ 395101-67-4 ]
Reference: [1] Patent: EP3205650, 2017, A1,
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