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[ CAS No. 1184172-46-0 ] {[proInfo.proName]}

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Chemical Structure| 1184172-46-0
Chemical Structure| 1184172-46-0
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Product Details of [ 1184172-46-0 ]

CAS No. :1184172-46-0 MDL No. :MFCD13189885
Formula : C5H3ClFNO Boiling Point : -
Linear Structure Formula :- InChI Key :KMUSIJQLKVODNC-UHFFFAOYSA-N
M.W : 147.54 Pubchem ID :70700710
Synonyms :

Calculated chemistry of [ 1184172-46-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.23
TPSA : 33.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.38
Log Po/w (XLOGP3) : 1.56
Log Po/w (WLOGP) : 2.0
Log Po/w (MLOGP) : 0.85
Log Po/w (SILICOS-IT) : 2.01
Consensus Log Po/w : 1.56

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.23
Solubility : 0.867 mg/ml ; 0.00588 mol/l
Class : Soluble
Log S (Ali) : -1.87
Solubility : 2.01 mg/ml ; 0.0136 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.32
Solubility : 0.7 mg/ml ; 0.00474 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.77

Safety of [ 1184172-46-0 ]

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

Application In Synthesis of [ 1184172-46-0 ]

* 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 [ 1184172-46-0 ]
  • Downstream synthetic route of [ 1184172-46-0 ]

[ 1184172-46-0 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 17282-04-1 ]
  • [ 1184172-46-0 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane for 2 h;
Stage #3: With peracetic acid In tetrahydrofuran; hexane; water; acetic acid at 0℃; for 1 h;
A solution of 2-chloro-3-fluoropyridine (2 mmol) in anhydrous THF (10ml) was cooled to -780C. To this solution was added a solution of lithium diisopropylamide (LDA; 2.2 mmol) in hexane slowly at same temperature. After 2h at -780C, to the mixture was added trimethoxyborane (0.48ml) and stirred for 2h, followed by an addition of peracetic acid (0.72 ml; 32percent in dilute acetic acid). The mixture was allowed to warm to O0C under stirring for Ih, then cooled to -2O0C, sodium dithionite (0.8g in 2ml water) was added dropwise. The mixture was extracted with ethyl acetate and the extract was <n="24"/>dried and concentrated. The residue was purified by chromatography, eluting with 1:19 MeOH:DCM to give the expected product as a white solid (80percent).
80%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2 h; Inert atmosphere
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78℃; for 2 h;
Stage #3: With peracetic acid In tetrahydrofuran; hexane; acetic acid at 0℃; for 1 h;
2-Chloro-3-fluoro-4-hydroxypyridine (10): A solution of 2-chloro-3-fluoropyridine (2 mmol) in anhydrous THF (10 ml) wascooled to 78 8C. To this solution was added a solution of lithiumdiisopropylamide (LDA; 2.2 mmol) in hexane slowly at sametemperature. After 2 h at 78 8C, to the mixture was addedtrimethoxyborane (0.48 ml) and stirred for 2 h, followed by anaddition of peracetic acid (0.72 ml; 32percent in dilute acetic acid). Themixture was allowed to warm to 0 8C under stirring for 1 h. Afterthe mixture was cooled to 20 8C, sodium dithionite (0.8 g in 2 mlwater) was added dropwise. The mixture was extracted with ethylacetate and the extract was dried and concentrated. The residuewas purified by chromatography, eluting with 1:19 MeOH:DCM togive the expected product as a white solid [19] (80percent). 1H NMR (d6-DMSO): d 11.86 (brs, 1H, OH), 7.89 (d, J = 5.3 Hz, 1H, C6–H), 6.95 (t,J = 5.8 Hz, 1H, C5–H). 19F NMR (d6-DMSO): d 141.29 (s). ESI-MS:148 (M+1)+.
Reference: [1] Patent: WO2009/103950, 2009, A1, . Location in patent: Page/Page column 22-23
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2185 - 2195
[3] Dalton Transactions, 2012, vol. 41, # 21, p. 6549 - 6557
[4] Journal of Fluorine Chemistry, 2015, vol. 173, p. 29 - 34
[5] Tetrahedron Letters, 2010, vol. 51, # 40, p. 5230 - 5233
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