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[ CAS No. 1204296-03-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1204296-03-6
Chemical Structure| 1204296-03-6
Chemical Structure| 1204296-03-6
Structure of 1204296-03-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1204296-03-6 ]

CAS No. :1204296-03-6 MDL No. :MFCD14525492
Formula : C6H4ClF2N Boiling Point : -
Linear Structure Formula :- InChI Key :CQNIYQCVDLBGPY-UHFFFAOYSA-N
M.W : 163.55 Pubchem ID :45790949
Synonyms :

Calculated chemistry of [ 1204296-03-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.31
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) : -5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.68
Log Po/w (XLOGP3) : 2.43
Log Po/w (WLOGP) : 3.19
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 2.86
Consensus Log Po/w : 2.44

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.76
Solubility : 0.282 mg/ml ; 0.00173 mol/l
Class : Soluble
Log S (Ali) : -2.34
Solubility : 0.742 mg/ml ; 0.00453 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.24
Solubility : 0.0945 mg/ml ; 0.000578 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.55

Safety of [ 1204296-03-6 ]

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 [ 1204296-03-6 ]

* 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 [ 1204296-03-6 ]
  • Downstream synthetic route of [ 1204296-03-6 ]

[ 1204296-03-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 101066-61-9 ]
  • [ 1204296-03-6 ]
YieldReaction ConditionsOperation in experiment
71% With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; Example 7: Preparation of 2-chloro-4-(difluoromethyl)pyridine 2-Chloropyridine-4-carbaldehyde (990mg, 7.0mM) was dissolved in dichloromethane (40ml_) with stirring and the solution cooled to 0-5°C. Diethylamino sulfurtrifluoride (2.82g, 2.31 ml, 17.5mM) was added drop-wise over 15 minutes, keeping the reaction temperature below 5°C. The solution was stirred in the cold for 2 hours, allowed to warm slowly to room temperature and stood overnight. The reaction mixture was gradually added to saturated sodium hydrogen carbonate solution (30ml_) and ice (100ml_), making sure that the pH of the solution was >7 at all times. After 30 minutes the mixture was diluted with dichloromethane (30ml_) and water (20ml_) and the organic phase separated. The aqueous phase was further extracted with dichloromethane (2 x 20ml_). The organic extracts were combined, washed with water, dried over magnesium sulfate, filtered and the filtrate evaporated giving a yellow liquid which was chromatographed to give 2- chloro-4-(difluoromethyl)pyridine as a colourless liquid (813mg, 71 percent) H NMR (CDCI3): δ 8.54 (d, 1 H); 7.81 (dd, 1 H); 7.45 (d, 1 H); 6.71 (t, 1 H)
71% With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; 2-Chloropyridine-4-carbaldehyde (990mg, 7.0mM) was dissolved in dichloromethane (4OmL) with stirring and the solution cooled to 0-5°C. Diethylamino sulfurtrifluoride (2.82g, 2.31 ml, 17.5mM)was added drop-wise over 15 minutes, keeping the reaction temperature below 5°C. The solution was stirred in the cold for 2 hours, allowed to warm slowly to room temperature and stood overnight. The reaction mixture was gradually added to saturated sodium hydrogen carbonate solution (3OmL) and ice (lOOmL), making sure that the pH of the solution was >7 at all times. After 30 minutes the mixture was diluted with dichloromethane (3OmL) and water (2OmL) and theorganic phase separated. The aqueous phase was further extracted with dichloromethane (2 x2OmL). The organic extracts were combined, washed with water, dried over magnesium sulfate, filtered and the filtrate evaporated giving a yellow liquid which was chromatographed to give 2-chloro-4-(difluoromethyl)pyridine as a colourless liquid (813mg, 71 percent)1H NMR (CDCI3): ö 8.54 (d, 1H); 7.81 (dd, 1H); 7.45 (d, 1H); 6.71 (t, 1H)
60.6% With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; for 12 h; Inert atmosphere DAST (20.53 mL, 155.42 mmol) was added dropwise to 2-chloroisonicotinaldehyde (10 g, 70.64 mmol) in DCM (150 mL) at 0°C over a period of 10 minutes under nitrogen. The temperature was increased to room temperature and stirred for 12 hours. The reaction mixture was quenched and adjusted to pH 7-8 with saturated NaHC03 at 0°C. The aqueous phase was extracted with DCM (3 x 150 mL), the organic phases dried over Na2S04, filtered and evaporated to afford yellow oil. The crude product was purified by flash silica chromatography, elution gradient 5 to 10percent EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford 2-chloro-4-(dif uoromethyl)pyridine (Intermediate 86; 7.00 g, 60.6percent) as a yellow oil. H NMR (400 MHz, CDC1 , 20.5 °C) δ 6.65 (1H, t), 7.38 (1H, dd), 7.49 (1H, s), 8.55 (1H, dd). m/z (ES+), [M+H]+ = 164.
Reference: [1] Patent: WO2015/18432, 2015, A1, . Location in patent: Page/Page column 54
[2] Patent: WO2015/18431, 2015, A1, . Location in patent: Page/Page column 61; 62
[3] Patent: WO2017/80979, 2017, A1, . Location in patent: Page/Page column 175
[4] Patent: WO2016/95204, 2016, A1, . Location in patent: Page/Page column 52; 53
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