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[ CAS No. 216076-11-8 ] {[proInfo.proName]}

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Chemical Structure| 216076-11-8
Chemical Structure| 216076-11-8
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Product Details of [ 216076-11-8 ]

CAS No. :216076-11-8 MDL No. :MFCD04114383
Formula : C13H10ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :BMSUUDSMTHMTQQ-UHFFFAOYSA-N
M.W : 231.68 Pubchem ID :11379248
Synonyms :

Calculated chemistry of [ 216076-11-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 63.93
TPSA : 29.96 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 2.61
Log Po/w (WLOGP) : 3.16
Log Po/w (MLOGP) : 2.21
Log Po/w (SILICOS-IT) : 3.84
Consensus Log Po/w : 2.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.28
Solubility : 0.122 mg/ml ; 0.000528 mol/l
Class : Soluble
Log S (Ali) : -2.89
Solubility : 0.299 mg/ml ; 0.00129 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.52
Solubility : 0.000703 mg/ml ; 0.00000303 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 216076-11-8 ]

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 [ 216076-11-8 ]

* 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 [ 216076-11-8 ]

[ 216076-11-8 ] Synthesis Path-Upstream   1~3

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YieldReaction ConditionsOperation in experiment
71% With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane; water REFERENCE EXAMPLE 16
1-(2-Chlorophenyl)-2-(4-pyridyl)ethanone
To a stirred solution of diisopropylamine (15.4 mL) in dry tetrahydrofuran (100 mL) cooled at -50° C., was added a solution of 1.6 M n-butyllithium in hexane (69 mL) dropwise.
After addition, the resulting mixture was stirred for 10 min at the same temperature, followed by the addition of a solution of γ-picoline (20 g) in dry tetrahydrofuran (10 mL) at -30° C.
After an additional 1 h stirring, a solution of N-(2-chlorobenzoyl)propyleneimine (20 g) in dry tetrahydrofuran (10 mL) was added dropwise to the resulting mixture at -10° C.
After addition the mixture was stirred for another 2 h at ambient temperature.
Water (100 mL) was added to the mixture and extracted with ethyl acetate.
The extract was washed with water, dried, and concentrated under reduced pressure.
The residue was purified using silica-gel column chromatography (hexane-ethyl acetate, 1:1) to give the title compound (16.4 g, yield 71percent).
oil. 1H-NMR (CDCl3) δ: 4.28 (2H, s), 7.20 (2H, d, J=6.2 Hz,), 7.28-7.39 (1H, m), 7.41-7.48 (3H, m), 8.56 (2H, d, J=6.2 Hz).
71% With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane; water Reference Example A 16
1-(2-chlorophenyl)-2-(4-pyridyl)ethanone
A solution of diisopropylamine (15 mL) in anhydrous tetrahydrofuran (100 mL) was cooled at -50OEC and 1.6 M n-butyllithium/hexane solution (69 mL) was added dropwise with stirring.
After completion of dropwise addition, the mixture was stirred for 10 min and a solution of γ-picoline (20 g) in anhydrous tetrahydrofuran (10 mL) was added dropwise at -30OEC.
The mixture was stirred for 1 h and a solution of N-(2-chlorobenzoyl)propyleneimine (20 g) in anhydrous tetrahydrofuran (10 mL) was added dropwise at -10OEC.
After completion of dropwise addition, the mixture was stirred for at room temperature for 2 h.
To the reaction mixture was added water (100 mL) and the mixture was extracted with ethyl acetate.
The extract was washed with water, and after drying, the solvent was evaporated.
The residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1) to give the title compound (16 g, yield 71percent).
oil.
1H-NMR (CDCl3) δ: 4.28 (2H, s), 7.20 (2H, d, J= 6.2 Hz), 7.28-7.39 (1H, m), 7.41-7.48 (3H, m), 8.56 (2H, d, J= 6.2 Hz).
71% With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane; water Reference Example A 16
1-(2-chlorophenyl)-2-(4-pyridyl)ethanone
A solution of diisopropylamine (15 mL) in anhydrous tetrahydrofuran (100 mL) was cooled at -50°C and 1.6 M n-butyllithium/hexane solution (69 mL) was added dropwise with stirring.
After completion of dropwise addition, the mixture was stirred for 10 min and a solution of γ-picoline (20 g) in anhydrous tetrahydrofuran (10 mL) was added dropwise at -30°C.
The mixture was stirred for 1 h and a solution of N-(2-chlorobenzoyl)propyleneimine (20 g) in anhydrous tetrahydrofuran (10 mL) was added dropwise at -10°C.
After completion of dropwise addition, the mixture was stirred for at room temperature for 2 h.
To the reaction mixture was added water (100 mL) and the mixture was extracted with ethyl acetate.
The extract was washed with water, and after drying, the solvent was evaporated.
The residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1) to give the title compound (16 g, yield 71percent).
oil
1H-NMR (CDCl3) δ: 4.28 (2H, s), 7.20 (2H, d, J= 6.2 Hz), 7.28-7.39 (1H, m), 7.41-7.48 (3H, m), 8.56 (2H, d, J= 6.2 Hz).
71% With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane; water Reference Example 16
1-(2-chlorophenyl)-2-(4-pyridyl)ethanone
A solution of diisopropylamine (15 mL) in anhydrous tetrahydrofuran (100 mL) was cooled at -50°C and 1.6 M n-butyllithium/hexane solution (69 mL) was added dropwise with stirring.
After completion of dropwise addition, the mixture was stirred for 10 min and a solution of γ-picoline (20 g) in anhydrous tetrahydrofuran (10 mL) was added dropwise at -30°C.
The mixture was stirred for 1 h and a solution of N-(2-chlorobenzoyl)propyleneimine (20 g) in anhydrous tetrahydrofuran (10 mL) was added dropwise at -10°C.
After completion of dropwise addition, the mixture was stirred for at room temperature for 2 h.
To the reaction mixture was added water (100 mL) and the mixture was extracted with ethyl acetate.
The extract was washed with water, and after drying, the solvent was evaporated.
The residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1) to give the title compound (16 g, yield 71percent).
oil.
1H-NMR (CDCl3) δ: 4.28 (2H, s), 7.20 (2H, d, J= 6.2 Hz), 7.28-7.39 (1H, m), 7.41-7.48 (3H, m), 8.56 (2H, d, J= 6.2 Hz).

Reference： [1] Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 4, p. 410 - 418
[2] Patent: US6436966, 2002, B1,
[3] Patent: EP1354603, 2003, A1,
[4] Patent: EP1402900, 2004, A1,
[5] Patent: EP1205478, 2002, A1,
[6] Chemical and Pharmaceutical Bulletin, 2008, vol. 56, # 8, p. 1126 - 1137
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YieldReaction ConditionsOperation in experiment
47%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran; cyclohexane at -78 - 0℃; for 0.5 h;
Stage #2: at -78 - 20℃; 		To lithium diisopropyl amide (6.5 mL, 1.6 M in cyclohexane, 10.4 mmol) in THF (20.0 mL) at -78 °C was added a solution of 4-picoline (1.07g mL, 11.5 mmol) in THF (10.0 mL) dropwise. The dry ice bath was removed. The reaction mixture was stirred at 0 "C for 30 minutes, and cooled back to -78 °C. A solution of 2-chloro-N-methoxy-N- methylbenzamide (21) (2.39 g, 12 mmol) in THF (10.0 mL) was added dropwise. The reaction mixture was warmed to room temperature and stirred overnight. White solid was filtered off and dissolved in ethyl acetate. The organic phase was washed with water, brine, dried over dried magnesium sulfate and concentrated under vacuum to give l-(2-chlorophenyl)-2-(pyridin-4-yl)ethanone (22) (1.09 g, 4.7 mmol, 47percent) as white solid.
47%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran; cyclohexane at -78 - 20℃;
Stage #2: at -78 - 20℃; 		l-(2-Chlorophenyl)-2-(pyridin-4-yl)ethanone (22): To lithium diisopropyl amide (6.5 mL, 1.6 M in cyclohexane, 10.4 mmol) in THF (20.0 mL) at -78 0C was added a solution of 4-picoline (1.07g mL, 1 1.5 mmol) in THF (10.0 mL) dropwise. The dry ice bath was removed. The reaction mixture was stirred at 0 0C for 30 minutes, and cooled back to -78 0C. A solution of 2-chloro-N-methoxy-N-methylbenzamide (21) (2.39 g, 12 mmol) in THF (10.0 mL) was added dropwise. The reaction mixture was warmed to room temperature and stirred overnight. White solid was filtered off and dissolved in ethyl acetate. The organic phase was washed with water, brine, dried over dried magnesium sulfate and concentrated under vacuum to give l-(2-chlorophenyl)-2- (pyridin-4-yl)ethanone (22) (1.09 g, 4.7 mmol, 47percent) as white solid.
Reference： [1] Patent: WO2009/91759, 2009, A1, . Location in patent: Page/Page column 49
[2] Patent: WO2009/91760, 2009, A1, . Location in patent: Page/Page column 41
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Reference： [1] Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 4, p. 410 - 418
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