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[ CAS No. 1150315-87-9 ] {[proInfo.proName]}

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Chemical Structure| 1150315-87-9
Chemical Structure| 1150315-87-9
Structure of 1150315-87-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1150315-87-9 ]

CAS No. :1150315-87-9 MDL No. :MFCD24470947
Formula : C18H23FN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :NGAMWHLFIWBSHL-UHFFFAOYSA-N
M.W : 318.39 Pubchem ID :67531507
Synonyms :

Calculated chemistry of [ 1150315-87-9 ]

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.56
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 90.44
TPSA : 53.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.35
Log Po/w (XLOGP3) : 3.27
Log Po/w (WLOGP) : 3.97
Log Po/w (MLOGP) : 2.96
Log Po/w (SILICOS-IT) : 3.74
Consensus Log Po/w : 3.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.8
Solubility : 0.0501 mg/ml ; 0.000157 mol/l
Class : Soluble
Log S (Ali) : -4.06
Solubility : 0.0275 mg/ml ; 0.0000862 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.74
Solubility : 0.00577 mg/ml ; 0.0000181 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.57

Safety of [ 1150315-87-9 ]

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 [ 1150315-87-9 ]

* 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 [ 1150315-87-9 ]
  • Downstream synthetic route of [ 1150315-87-9 ]

[ 1150315-87-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 518070-26-3 ]
  • [ 118753-70-1 ]
  • [ 1150315-87-9 ]
YieldReaction ConditionsOperation in experiment
33%
Stage #1: With sodium hydride In dimethyl sulfoxide for 5 h;
Stage #2: at 0 - 20℃;
A: 1,1 -Dimethylethyl 4-cyano-4-(2-fluoro-4-methylphenyl)- 1 -piperidinecarboxylate(2-Fluoro-4-methylphenyl)acetonitrile (11.49 g, 77 mmol) was gradually added to a suspension of sodium hydride (11.70 g, 293 mmol) and DMSO (200 mL) in a 1-L round-bottomed flask fitted with a mechanical overhead stirrer. The reaction was stirred for about 5 hours, after which time the mixture was cooled in an ice bath. A mixture of 1,1 -dimethylethyl bis(2-chloroethyl)carbamate (20.38 g, 84 mmol) in 30 mL of DMSO was then added, and the resulting solution was allowed to warm to ambient temperature and stir overnight. Water was added slowly, and the organics were extracted with DCM (3 x 300 mL). The combined DCM extracts were washed with water (2 x 400 mL) then dried over sodium sulfate and concentrated. The product was purified on a 330 g silica gel column, eluting with 70-100percent hexanes in DCM. The product was obtained as a yellow oil (8.2g, 33percent). MS (ES) m/e 219.1[M+H]+.
33%
Stage #1: With sodium hydride In dimethyl sulfoxide for 5 h; Cooling with ice
Stage #2: at 20℃;
(2-Fluoro-4-methylphenyl)acetonitrile (11.49 g, 77 mmol) was gradually added to a suspension of sodium hydride (11.70 g, 293 mmol) and DMSO (200 mL) in a 1-L round- bottomed flask fitted with a mechanical overhead stirrer. The reaction was stirred for about 5 h, after which time the mixture was cooled in an ice bath. A mixture of 1,1- dimethylethyl bis(2-chloroethyl)carbamate (20.38 g, 84 mmol) in DMSO (30 mL) was then added, and the resulting solution was allowed to warm to room temperature and stir overnight. Water was added slowly, and the organics were extracted with DCM (3 x 300 mL). The combined DCM extracts were washed with water (2 x 400 mL) then dried over sodium sulfate and concentrated. The product was purified on a 330 g silica gel column, eluting with 70-100percent hexanes in DCM. The product was obtained as a yellow oil (8.2g, 33percent). MS (ES) m/e 219.1 [M+H]+.
Reference: [1] Patent: WO2009/61881, 2009, A1, . Location in patent: Page/Page column 23
[2] Patent: WO2010/80873, 2010, A1, . Location in patent: Page/Page column 36
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