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[ CAS No. 4532-25-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 4532-25-6
Chemical Structure| 4532-25-6
Chemical Structure| 4532-25-6
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Product Details of [ 4532-25-6 ]

CAS No. :4532-25-6 MDL No. :MFCD08275126
Formula : C7H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :NGHRUBVFDAKWBC-UHFFFAOYSA-N
M.W : 152.58 Pubchem ID :19695901
Synonyms :

Calculated chemistry of [ 4532-25-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.2
TPSA : 17.3 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) : -5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.87
Log Po/w (XLOGP3) : 2.39
Log Po/w (WLOGP) : 1.99
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 1.63
Consensus Log Po/w : 1.84

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.96
Solubility : 0.168 mg/ml ; 0.0011 mol/l
Class : Soluble
Log S (Ali) : -2.39
Solubility : 0.615 mg/ml ; 0.00403 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.68
Solubility : 0.316 mg/ml ; 0.00207 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 4532-25-6 ]

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

Application In Synthesis of [ 4532-25-6 ]

* 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 [ 4532-25-6 ]
  • Downstream synthetic route of [ 4532-25-6 ]

[ 4532-25-6 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 107-20-0 ]
  • [ 19798-80-2 ]
  • [ 4532-25-6 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydrogencarbonate In ethanol; water at 20℃; for 20 h; Reflux Synthesis of 7-Chloroimidazo[1 , 2-a]pyridine (compound 65-3)[0000229] To a suspension of compound 65-2 (HC1) in ethanol (15 mL) was added sodium bicarbonate powder (3.3g, 38.4 mmol, 4 equiv) and a 50percent solution of chloroacetaldehyde in water (2.26 g, 14.4 mmol, 1.5 equiv) . The reaction was heated at reflux for 4 hours and stirred at room temperature for 16 hours. The reaction was concentrated under reduced pressure and the residue was dissolved in water (10 mL) and ethyl acetate (10 mL) . The layers were separated and the aqueous phase was extracted with ethyl acetate (2 x 5 mL) . The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give compound 65-3 as a dark yellow oil (980 mg, 89percent yield)
85% for 2 h; Reflux (2a)
7-Chloroimidazo[1,2-a]pyridine
Into ethanol (50 mL), 2-amino-4-chloropyridine (643 mg, 5.00 mmol) was dissolved, to which a 40percent aqueous solution of chloroacetaldehyde (8.25 mL, 50 mmol) was added, followed by heating under reflux for two hours.
The resulting mixture was left to cool, and the solvent was distilled off under reduced pressure.
The residue thus obtained was purified by basic silica gel column chromatography (dichloromethane) to give the desired title compound (645 mg, yield 85percent).
1H-NMR (CDCl3) δ: 6.79 (1H, dd, J = 7.4, 2.3 Hz), 7.57 (1H, s), 7.63 (2H, br s), 8.05 (1H, d, J = 7.4 Hz).
79% at 130℃; for 12 h; General procedure: 2-aminopyridine (15 g, 0.159 M) was dissolved in 1-butanol (64 mL) in a 250 mL round bottom flask affixed with a magnetic stir bar. 2-chloroacetaldehyde 50percent solution in water (24.3 mL, 0.191 M) was added hitherto and the reaction was heated to 130 °C for 12 h.The reaction solvent was condensed in vacuo and the crude product was adsorbed onto silica. The product was purified via flash chromatography utilizing a DCM/MeOH gradient and isolated as a light, yellow oil (17 g, 90percent).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 3, p. 750 - 756
[2] Patent: WO2013/123215, 2013, A2, . Location in patent: Paragraph 0000229
[3] Patent: EP2565185, 2013, A1, . Location in patent: Paragraph 0114-0115
[4] European Journal of Medicinal Chemistry, 2015, vol. 94, p. 123 - 131
[5] Patent: WO2008/78100, 2008, A2, . Location in patent: Page/Page column 93-94
[6] Patent: WO2009/47506, 2009, A1, . Location in patent: Page/Page column 110; 111
[7] Patent: WO2009/50183, 2009, A2, . Location in patent: Page/Page column 114
[8] Patent: WO2018/136634, 2018, A1, . Location in patent: Page/Page column 40; 41
[9] Patent: WO2009/150240, 2009, A1, . Location in patent: Page/Page column 101
  • 2
  • [ 130721-78-7 ]
  • [ 4532-25-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 3, p. 750 - 756
[2] Patent: WO2013/123215, 2013, A2,
  • 3
  • [ 4532-25-6 ]
  • [ 342613-67-6 ]
Reference: [1] Patent: WO2009/50183, 2009, A2, . Location in patent: Page/Page column 114
  • 4
  • [ 4532-25-6 ]
  • [ 896139-85-8 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 41, p. 13493 - 13496
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