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[ CAS No. 60186-15-4 ]

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Chemical Structure| 60186-15-4
Chemical Structure| 60186-15-4
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Product Details of [ 60186-15-4 ]

CAS No. :60186-15-4 MDL No. :MFCD18802741
Formula : C5H2F2N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OLPMWQXRTRVQRS-UHFFFAOYSA-N
M.W :160.08 Pubchem ID :12275767
Synonyms :

Calculated chemistry of [ 60186-15-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 32.98
TPSA : 58.71 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) : -6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.87
Log Po/w (XLOGP3) : 1.22
Log Po/w (WLOGP) : 2.11
Log Po/w (MLOGP) : 0.95
Log Po/w (SILICOS-IT) : 0.15
Consensus Log Po/w : 1.06

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.94
Solubility : 1.84 mg/ml ; 0.0115 mol/l
Class : Very soluble
Log S (Ali) : -2.05
Solubility : 1.43 mg/ml ; 0.00891 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.95
Solubility : 1.78 mg/ml ; 0.0111 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.21

Safety of [ 60186-15-4 ]

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

Application In Synthesis of [ 60186-15-4 ]

* 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 [ 60186-15-4 ]
  • Downstream synthetic route of [ 60186-15-4 ]

[ 60186-15-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 4487-56-3 ]
  • [ 60186-15-4 ]
YieldReaction ConditionsOperation in experiment
85% With potassium fluoride; 18-crown-6 ether In 1-methyl-pyrrolidin-2-one at 100℃; for 3 h; Inert atmosphere 2,4-Difluoro-5-nitropyridine.In a 250 mL round-bottom flask was added 2,4- dichloro-5-nitropyridine (0.73 g,3.8 mmol), potassium fluoride (0.659 g, 11.3 mmol), and 18-crown-6 (0.160 g,0.605 mmol) in N-methylpyrrolidinone (3 mL) to give a tan suspension. Themixture was heated at 100°C under nitrogen for 3 h. The mixture was thenpartitioned between water and ether/hexane. The organic layer was washed withwater, brine, dried and concentrated to give a tan solid (0.515 g, 85percent): 1H NMR(400 MHz, CDC13) δ 9.07 (d, J = 9.7 Hz, 1H), 6.96 (dd, J = 9.5, 2.5 Hz,1H);19F NMR (376 MHz, CDC13) δ -52.20 (d, J = 29.3 Hz), -98.13 (d, J = 28.9 Hz).
79% With potassium fluoride; 18-crown-6 ether In 1-methyl-pyrrolidin-2-one at 100℃; for 3 h; Inert atmosphere Sledeski, A.W.; Kubiak, G.G. ; O'Brien, M.K. : Powers, M.R.; Powner, T.H. ; Truesdale, L.K. J. Org. Chem. 2000, 65, 8114-8118. In a 250 mL round-bottomed flask was 2,4-dichloro-5-nitropyridine (4.27 g, 22.13 mmol), (0082) POTASSIUM FLUORIDE (3.86 g, 66.4 mmol), and 18C6 (0.936 g, 3.54 mmol) in NMP (15 mL) to give a tan suspension. The mixture was heated at 100°C under nitrogen for 3 h. LCMS showed complete conversion to a new peak. The mixture was then partitioned between water and ether (with some hexane: better for getting rid of NMP). The organic layer was washed with water, brine, dried and concentrated to a tan oil. It became solid (2.8 g, 79percent) when cooled in frige. The material was used as is.
47% With potassium fluoride; 18-crown-6 ether In 1-methyl-pyrrolidin-2-one at 100℃; for 2 h; Inert atmosphere A mixture of 2,4-dichloro-5-nitropyridine (450 mg, 2.332 mmol), potassium fluoride (406 mg, 7.00 mmol), and 18-Crown-6 (99 mg, 0.373 mmol) in NMP (2 mL) was heated at 100°C under nitrogen for 2 h. The reaction mixture was transferred to a separatory funnel containing water (5 mL) and ether (50 mL). The layers were separated and the organic layer was washed with water (2 x 5 mL), brine (5 mL), dried over MgS04, filtered, and concentrated. The residue was purified by column chromatography on silica gel (10percent→ 20percent ethyl acetate in hexanes; 40 g column) to afford 2,4-difluoro-5-nitropyridine (177 mg, 1.106 mmol, 47percent yield) as a colorless solid: NMR (400MHz, CDCh) δ 9.07 (d, J=9.5 Hz, 1H), 6.95 (dd, J=9A, 2.4 Hz, 1H); 19 F NMR (376MHz, CDCh) δ -52.17 (d, J=27.7 Hz, IF), -98.12 (dt, J=29.5, 8.7 Hz, IF).
Reference: [1] Patent: WO2015/69594, 2015, A1, . Location in patent: Page/Page column 106
[2] Patent: WO2018/98413, 2018, A1, . Location in patent: Page/Page column 16
[3] Patent: WO2018/98411, 2018, A1, . Location in patent: Page/Page column 94; 95
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