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[ CAS No. 1373503-66-2 ] {[proInfo.proName]}

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Chemical Structure| 1373503-66-2
Chemical Structure| 1373503-66-2
Structure of 1373503-66-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1373503-66-2 ]

CAS No. :1373503-66-2 MDL No. :MFCD21602014
Formula : C8H16Cl2F2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :KACPIXHEWFBPBD-UHFFFAOYSA-N
M.W : 249.13 Pubchem ID :71464189
Synonyms :

Calculated chemistry of [ 1373503-66-2 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.94
TPSA : 15.27 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
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) : 0.0
Log Po/w (XLOGP3) : 2.44
Log Po/w (WLOGP) : 2.37
Log Po/w (MLOGP) : 1.81
Log Po/w (SILICOS-IT) : 1.67
Consensus Log Po/w : 1.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.86
Solubility : 0.347 mg/ml ; 0.00139 mol/l
Class : Soluble
Log S (Ali) : -2.4
Solubility : 0.983 mg/ml ; 0.00395 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.8
Solubility : 3.95 mg/ml ; 0.0158 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 1373503-66-2 ]

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 [ 1373503-66-2 ]

* 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.

  • Downstream synthetic route of [ 1373503-66-2 ]

[ 1373503-66-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1373503-66-2 ]
  • [ 116922-60-2 ]
  • [ 2773324-27-7 ]
YieldReaction ConditionsOperation in experiment
19% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 120℃; for 2h; 207.3 Step 3: Synthesis of 3-bromo-4-[4-(3,3-difluoroazetidin-1-yl)-1-piperidyl]pyridine To a solution of 4-(3,3-difluoroazetidin-1-yl)piperidine hydrochloric acid salt (400 mg, 1.9 mmol) and 3-bromo-4-fluoro-pyridine (331 mg, 1.9 mmol) in N,N-dimethylacetamide (15 mL) was added N,N-diisopropylethylamine (1.22 g, 9.4 mmol) at room temperature. The resulting mixture was stirred at 120 °C for 2 hours and then cooled to room temperature. Purification via reverse phase column chromatography (acetonitrile/water) afforded the title compound as a yellow solid. Yield: 130 mg, 19%. LCMS (ESI) m/z: 332.2 (M+H).
19% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 120℃; for 2h; 207.3 Step 3: Synthesis of 3-bromo-4-[4-(3,3-difluoroazetidin-1-yl)-1-piperidyl]pyridine To a solution of 4-(3,3-difluoroazetidin-1-yl)piperidine hydrochloric acid salt (400 mg, 1.9 mmol) and 3-bromo-4-fluoro-pyridine (331 mg, 1.9 mmol) in N,N-dimethylacetamide (15 mL) was added N,N-diisopropylethylamine (1.22 g, 9.4 mmol) at room temperature. The resulting mixture was stirred at 120 °C for 2 hours and then cooled to room temperature. Purification via reverse phase column chromatography (acetonitrile/water) afforded the title compound as a yellow solid. Yield: 130 mg, 19%. LCMS (ESI) m/z: 332.2 (M+H).
  • 2
  • [ 1093066-74-0 ]
  • [ 1373503-66-2 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogenchloride In lithium hydroxide monohydrate; ethyl acetate at 20℃; for 2h; 207.2 Step 2: Synthesis of 4-(3,3-difluoroazetidin-1-yl)piperidine hydrochloric acid salt To a solution of tert-butyl 4-(3,3-difluoroazetidin-1-yl)piperidine-1-carboxylate (500 mg, 1.8 mmol) in ethyl acetate (20 mL) was added 2 M hydrogen chloride in ethyl acetate (9 mL, 18 mmol). The resulting mixture was stirred at room temperature for 2 hours and then filtered. The solid was collected and dried in air to afford the title compound as a white solid. Yield: 450 mg, 94%.1H NMR (DMSO-d6, 400 MHz): δ 8.93 (s, 1H), 4.75 (s, 4H), 3.52-3.66 (m, 1H), 3.37-3.46 (m, 2H), 2.74-2.86 (m, 2H), 2.06-2.14 (m, 2H), 1.75-1.91 (m, 2H).
94% With hydrogenchloride In lithium hydroxide monohydrate; ethyl acetate at 20℃; for 2h; 207.2 Step 2: Synthesis of 4-(3,3-difluoroazetidin-1-yl)piperidine hydrochloric acid salt To a solution of tert-butyl 4-(3,3-difluoroazetidin-1-yl)piperidine-1-carboxylate (500 mg, 1.8 mmol) in ethyl acetate (20 mL) was added 2 M hydrogen chloride in ethyl acetate (9 mL, 18 mmol). The resulting mixture was stirred at room temperature for 2 hours and then filtered. The solid was collected and dried in air to afford the title compound as a white solid. Yield: 450 mg, 94%.1H NMR (DMSO-d6, 400 MHz): δ 8.93 (s, 1H), 4.75 (s, 4H), 3.52-3.66 (m, 1H), 3.37-3.46 (m, 2H), 2.74-2.86 (m, 2H), 2.06-2.14 (m, 2H), 1.75-1.91 (m, 2H).
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