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[ CAS No. 514797-97-8 ] {[proInfo.proName]}

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Chemical Structure| 514797-97-8
Chemical Structure| 514797-97-8
Structure of 514797-97-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 514797-97-8 ]

CAS No. :514797-97-8 MDL No. :MFCD11044268
Formula : C5H2BrClFN Boiling Point : -
Linear Structure Formula :- InChI Key :PYDGFYYLQFJQBZ-UHFFFAOYSA-N
M.W :210.43 Pubchem ID :10965798
Synonyms :

Calculated chemistry of [ 514797-97-8 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.91
TPSA : 12.89 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) : -5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.98
Log Po/w (XLOGP3) : 2.6
Log Po/w (WLOGP) : 3.06
Log Po/w (MLOGP) : 2.28
Log Po/w (SILICOS-IT) : 3.17
Consensus Log Po/w : 2.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.28
Solubility : 0.111 mg/ml ; 0.00053 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.636 mg/ml ; 0.00302 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.78
Solubility : 0.035 mg/ml ; 0.000166 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.95

Safety of [ 514797-97-8 ]

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 [ 514797-97-8 ]

* 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 [ 514797-97-8 ]
  • Downstream synthetic route of [ 514797-97-8 ]

[ 514797-97-8 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 514797-97-8 ]
  • [ 514797-99-0 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 24, p. 4174 - 4180
  • 2
  • [ 246847-98-3 ]
  • [ 514797-97-8 ]
YieldReaction ConditionsOperation in experiment
90% at 0℃; for 0.333333 h; Step 1: 2-bromo-5-chloro-3-fluoropyridine [0218] 5-chloro-3-fluoropyridin-2-amine (5.0 g, 34 mmol) was slowly added to 48percent HBr solution (20 mL) with stirring at 0°C. To the resulting mixture E (5.24 mL, 102.3 mmol) was then added over 20 minutes at 0°C. The reaction mixture was cooled to -10°C. A solution of NaNC"2 (5.88 g, 85.3 mmol) in water (20 mL) was added over 1.5 hours, and the mixture stirred for additional 30 minutes. A solution of NaOH (12 g, 306 mmol) in water (20 mL) was added over 30 minutes, and the mixture was allowed to warm to room temperature. The mixture was extracted with ether (3x 100 mL). The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated to afford the title compound as pale yellow solid (6.43 g, 90percent). 1H NMR (400 MHz, CDC13) δ 8.23 (d, J = 2.1 Hz, 1H), 7.48 (dd, J= 7.1, 2.1 Hz, 1H).
90%
Stage #1: at 0℃; for 0.333333 h;
Stage #2: With sodium nitrite In water at -10℃; for 2 h;
Stage #3: With sodium hydroxide In water at 20℃; for 0.5 h;
5-chioro-3-fluoropvridin-2-amine (5.0 g, 34 turned) was slowly added to 48percent HBrpercentoluuon (20 ml) ith snwng ii 0 ( to 1 e iesultnig m11uie 13L ( 24 ml 102 ‘ mrnob was then added over 20 minute.s at 0 C. The reaction mixture was cooled to 1 0 ‘C. A solunon of NaNO2 (5.88 g, 85.3 mmol) in water (20 mL) was added over I .5 hours, and the mixture stirred for additional 30 minutes. A solution of NaOH. (12 g, 306 mmol) in water (20 mL) was added over 30 mmnutesand the mixture was allowed to warm to room temperature. Th.e mixture was extracted with ether (3 x 1 00 rnL). The combined orgamc phases were washed with brine, dried over sodium sulfate, filtered, and concentrated to afford the title compound as a pale yellow solid (6.43 g, 90percent). H NMR (400 MHz, CDCh 6 8.23 (d, 12.1 Hz, 111), 7.48 (dd, J’ 7.1. 21 Hz, IN).
Reference: [1] Patent: WO2015/187845, 2015, A1, . Location in patent: Paragraph 0218
[2] Patent: WO2016/44323, 2016, A1, . Location in patent: Paragraph 0323
  • 3
  • [ 514797-96-7 ]
  • [ 514797-97-8 ]
YieldReaction ConditionsOperation in experiment
74% With phosphorus(V) oxybromide In N,N-dimethyl-formamide at 130℃; for 1 h; Example 6(b) 2-Bromo-5-chloro-3-fluoropyridine. To solid 5-chloro-3-fluoro-2-hydroxypyridine (75 g, 0.51 mmol) was added melted POBr3 (150 g, 0.52 mmol). DMF (2 mL) was then added by pipet, and the mixture was heated at 130° C. for 1 h. The excess POBr3 was quenched by the careful addition of water to the reaction mixture at 0° C., and the resulting mixture was dissolved in a 2:1 mixture of EtOAc:water. The organic layer was washed three times with water and once with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The resulting yellow oil was passed through a plug of silica gel (10percent Et2O:90percent hexanes) to provide the title compound as a white solid (79.4 g, 74percent). The product was characterized by 1H NMR.
Reference: [1] Patent: US2008/242695, 2008, A1, . Location in patent: Page/Page column 36
[2] Patent: EP2305672, 2011, A1, . Location in patent: Page/Page column 88
  • 4
  • [ 514797-96-7 ]
  • [ 514797-97-8 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 24, p. 4174 - 4180
  • 5
  • [ 514798-05-1 ]
  • [ 514797-97-8 ]
  • [ 514798-09-5 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 24, p. 4174 - 4180
  • 6
  • [ 89402-43-7 ]
  • [ 514797-97-8 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 24, p. 4174 - 4180
[2] Patent: EP2305672, 2011, A1,
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