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[ CAS No. 228251-24-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 228251-24-9
Chemical Structure| 228251-24-9
Chemical Structure| 228251-24-9
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Product Details of [ 228251-24-9 ]

CAS No. :228251-24-9 MDL No. :MFCD08689713
Formula : C6H3BrClNO Boiling Point : -
Linear Structure Formula :- InChI Key :YGPYNLZCNDPHTQ-UHFFFAOYSA-N
M.W : 220.45 Pubchem ID :23090988
Synonyms :

Calculated chemistry of [ 228251-24-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.33
TPSA : 29.96 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) : -6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 1.97
Log Po/w (WLOGP) : 2.31
Log Po/w (MLOGP) : 1.16
Log Po/w (SILICOS-IT) : 2.83
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) : -2.83
Solubility : 0.329 mg/ml ; 0.00149 mol/l
Class : Soluble
Log S (Ali) : -2.22
Solubility : 1.31 mg/ml ; 0.00596 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.45
Solubility : 0.0784 mg/ml ; 0.000356 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 228251-24-9 ]

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 [ 228251-24-9 ]

* 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 [ 228251-24-9 ]
  • Downstream synthetic route of [ 228251-24-9 ]

[ 228251-24-9 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 78686-79-0 ]
  • [ 228251-24-9 ]
YieldReaction ConditionsOperation in experiment
74% With diisobutylaluminium hydride In dichloromethane at -78℃; for 2 h; To a (-78eC) cooled and stirred solution of methyl 5-bromo-2-chloronicotinate (10.0 g, 39.9 mmol) in DCM (100 mL) was added diBAL-H (43.9 mL, 43.9 mmol, 1.6 M in hexane) dropwise and then stirred for 2h at the same temperature. Reaction was quenched with 2M aqueous HCI (50 mL) and stirred for 30 min at room temperature. Reaction mixture was filtered through the celite. The layers were separated and the aqueous layer was extracted with ethyl acetate (2/1,100 mL). The combined organic layer was washed with brine (100 mL), dried (Na2S04) and filtered. The filtrate was concentrated under vacuum and the crude product was purified by flash column chromatography (silica gel, 20-30percent EtOAc in hexane system as eluent) to afford 6.50 g (74percent) of the titled compound. 1HNMR (400 MHz, DMSO- d6) U10.19 (s, 1H), 8.86 (brs, 1H), 8.40 (brs, 1H); GCMS (m/z) 218.94(M)\
Reference: [1] Patent: WO2018/20474, 2018, A1, . Location in patent: Page/Page column 157
[2] Patent: WO2011/103202, 2011, A2,
[3] Patent: WO2015/181747, 2015, A1,
  • 2
  • [ 742100-75-0 ]
  • [ 228251-24-9 ]
Reference: [1] Patent: WO2009/10801, 2009, A1, . Location in patent: Page/Page column 72
[2] Patent: EP1593673, 2005, A1, . Location in patent: Page/Page column 98
[3] Patent: WO2011/103202, 2011, A2, . Location in patent: Page/Page column 180
[4] Patent: WO2015/181747, 2015, A1, . Location in patent: Page/Page column 76
[5] Patent: WO2017/133701, 2017, A1, . Location in patent: Paragraph 157; 158
  • 3
  • [ 885223-63-2 ]
  • [ 228251-24-9 ]
YieldReaction ConditionsOperation in experiment
45% With lithium aluminium tetrahydride In tetrahydrofuran at -10 - 20℃; Preparation of S-bromo^-chloronicotinaldehyde (D-2-3).To a stirred solution of compound D-2-2 (25 g, 89.4 mmol) in dry THF (200 mL) was added LiAIH4 (1.7 g, 27 mmol) at -10 0C under N2 atmosphere. After the addition, the reaction mixture was allowed to warm up to room temperature and stirred overnight. TLC (petroleum ether/EtOAc 5:1 ) indicated complete consumption of starting material. To the reaction mixture was added 1 N KHSO4 (200 mL) and extracted with EtOAc (300 mL><3). The combined organic layers were washed with saturated aqueous NaCI (200 mL), dried over Na2SO4 and concentrated in vacuo to yield crude compound D-2-3, which was purified by column chromatography (silica gel, petroleum ether/EtOAc 30:1 ) to yield pure compound D-2-3 (8.0 g, 45percent) as a white solid.
Reference: [1] Patent: WO2009/16460, 2009, A2, . Location in patent: Page/Page column 104
[2] Patent: WO2017/133701, 2017, A1, . Location in patent: Paragraph 192; 193
  • 4
  • [ 29241-65-4 ]
  • [ 228251-24-9 ]
Reference: [1] Patent: WO2017/133701, 2017, A1,
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