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[ CAS No. 947248-52-4 ] {[proInfo.proName]}

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Chemical Structure| 947248-52-4
Chemical Structure| 947248-52-4
Structure of 947248-52-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 947248-52-4 ]

CAS No. :947248-52-4 MDL No. :MFCD09864902
Formula : C7H6BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :LAUJNLOJYLUKCP-UHFFFAOYSA-N
M.W : 212.05 Pubchem ID :44119296
Synonyms :

Calculated chemistry of [ 947248-52-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.3
TPSA : 43.32 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) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 2.11
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 1.27
Log Po/w (SILICOS-IT) : 0.9
Consensus Log Po/w : 1.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.09
Solubility : 0.173 mg/ml ; 0.000814 mol/l
Class : Soluble
Log S (Ali) : -2.65
Solubility : 0.474 mg/ml ; 0.00224 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.58
Solubility : 0.551 mg/ml ; 0.0026 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.88

Safety of [ 947248-52-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 947248-52-4 ]

* 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 [ 947248-52-4 ]
  • Downstream synthetic route of [ 947248-52-4 ]

[ 947248-52-4 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 504413-35-8 ]
  • [ 947248-52-4 ]
YieldReaction ConditionsOperation in experiment
77% With water; lithium hydroxide In tetrahydrofuran at 20℃; for 24 h; Intermediate 6: 6-bromoimidazo[1 ,2-a]pyridin-2 -amine A solution of Λ/-(6-bromoimidazo[1 ,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide (5.5 g, 18.2 mmol) and lithium hydroxide (1.2 g, 27.3 mmol) in THF/Water (5OmL, 7:3) was stirred at room temperature for 24h. THF was then removed under reduced pressure and the aqueous layer was extracted with DCM. Combined organic layers were then washed with brine, dried over sodium sulphate and concentrated under reduced pressure to give the titled compound as a pale brown solid (2.9 g, 77percent). HPLC (X-Terra), Rt: 3.07 min (purity: 97.0percent). LC/MS (Atlantis), M+(ESI): 214.1.1H-NMR (DMSO-d6, 400 MHz) δ 8.58-8.59 (1 H, s), 7.11-7.13 (1 H, d), 7.05-7.07 (1 H, d), 6.98 (1 H1 S), 5.19 (2H, s).
42% With methanol; water; potassium carbonate In tetrahydrofuran at 60℃; for 16 h; Step 4.
6-bromoimidazo[1,2-a]pyridin-2-amine
To a 250 mL round-bottomed flask was added N-(6-bromoH-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide (3.50 g, 11 mmol), THF (15 mL), methanol (15 mL), water (15 mL) and potassium carbonate (16 g, 114 mmol).
The mixture was stirred at 60° C. for 16 h.
After cooling to rt, the mixture was poured into water (100 mL) and extracted with CH2Cl2 (4*75 mL).
The combined extracts were washed with brine, dried (Na2SO4) and concentrated onto silica.
Purification by silica gel chromatography (0.5 to 5.0percent MeOH/CH2Cl2) afforded the title compound (1.01 g, 42percent). MS (ESI, positive ion) m/z: 212 (M(79Br)+1).
8.3 g With sodium hydroxide In ethanol at 80℃; A mixture of A81-3 (15 g, crude, 46 mmol) in 1 N NaOH/EtOH (50 mL/40 mL) was stirred at 80°C overnight. After cooled to r.t., the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Na2S04 and the solvent was removed by vacuum. The residue was recrystallized in petroleum ether to give a brown solid (8.3 g, 85percent). H NMR (400 MHz, DMSO-d<5) δ 8.60 (s, 1H), 7.32 -7.05 (m, 2H), 7.00 (s, 1H), 5.22 (s, 2H).
Reference: [1] Patent: WO2010/100144, 2010, A1, . Location in patent: Page/Page column 105
[2] Patent: US2009/163489, 2009, A1, . Location in patent: Page/Page column 33
[3] Patent: WO2009/10530, 2009, A1, . Location in patent: Page/Page column 74
[4] Patent: WO2007/95588, 2007, A1, . Location in patent: Page/Page column 65
[5] Patent: WO2018/17435, 2018, A1, . Location in patent: Paragraph 00119-00120
  • 2
  • [ 207801-52-3 ]
  • [ 947248-52-4 ]
Reference: [1] Patent: WO2018/17435, 2018, A1,
  • 3
  • [ 1072-97-5 ]
  • [ 947248-52-4 ]
Reference: [1] Patent: WO2018/17435, 2018, A1,
  • 4
  • [ 937014-94-3 ]
  • [ 947248-52-4 ]
Reference: [1] Patent: WO2018/17435, 2018, A1,
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