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[ CAS No. 774609-73-3 ] {[proInfo.proName]}

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Chemical Structure| 774609-73-3
Chemical Structure| 774609-73-3
Structure of 774609-73-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 774609-73-3 ]

CAS No. :774609-73-3 MDL No. :MFCD11111486
Formula : C12H20N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :WQWMUDUIUQIEII-UHFFFAOYSA-N
M.W : 240.30 Pubchem ID :25067313
Synonyms :

Calculated chemistry of [ 774609-73-3 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 67.16
TPSA : 73.56 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.11
Log Po/w (XLOGP3) : 1.04
Log Po/w (WLOGP) : 1.28
Log Po/w (MLOGP) : 0.5
Log Po/w (SILICOS-IT) : 0.97
Consensus Log Po/w : 1.18

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.72
Solubility : 4.57 mg/ml ; 0.019 mol/l
Class : Very soluble
Log S (Ali) : -2.18
Solubility : 1.61 mg/ml ; 0.00668 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.42
Solubility : 9.22 mg/ml ; 0.0384 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.35

Safety of [ 774609-73-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 774609-73-3 ]

* 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 [ 774609-73-3 ]
  • Downstream synthetic route of [ 774609-73-3 ]

[ 774609-73-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 79099-07-3 ]
  • [ 75-05-8 ]
  • [ 774609-73-3 ]
YieldReaction ConditionsOperation in experiment
41%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1 h; Inert atmosphere
Stage #2: at 20℃; for 1 h;
A solution of n-butyl lithium (2.5 M in hexanes, 12 mL, 30.1 mmol) was added dropwise to a pre- cooled solution at 0 °C of diisopropylamine (3.05 g, 30.1 mmol) in tetrahydrofuran (25 mL) under nitrogen atmosphere. The resulting mixture was stirred for 0.5 h at room temperature then cooled to -78 °C. To the reaction mixture was added dropwise a solution of acetonitrile (1.24 g, 30.2 mmol) in tetrahydrofuran at -78 °C. The mixture was stirred for 1 h at -78 °C then a solution of tert-butyl 4-oxopiperidine-l-carboxylate (3.0 g, 15.1 mmol) in tetrahydrofuran (12 mL) was added. The resulting solution was stirred for 1 h at room temperature. The reaction was quenched by ammonium chloride (aq . 100 mL), extracted with ethyl acetate, and the organic wash was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (solvent gradient: 0-20percent ethyl acetate in petroleum ether) to afford the title compound (1.5 g, 41 percent) as a white solid. LCMS (ESI): [M+H]+ = 241.
Reference: [1] Patent: WO2014/210354, 2014, A1, . Location in patent: Page/Page column 140
[2] Patent: WO2017/60874, 2017, A1, . Location in patent: Paragraph 00618-00619
[3] Patent: US2017/101406, 2017, A1, . Location in patent: Paragraph 1662; 1663
  • 2
  • [ 79099-07-3 ]
  • [ 590-17-0 ]
  • [ 774609-73-3 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1.16667 h;
Stage #2: at 20℃; for 2 h;
To an oven-dried flask equipped with a stirring bar and rubber septum was added anhydrous THF (250 mL). Diisopropylamine (7.0 mL, 50.2 mmole) was added and the solution cooled to-78 °C. To the cooled solution was added n-butyllithium (1.6 M in hexanes, 31 mL, 50.2 MMOLE) over 10 minutes. The reaction mixture was stirred for 60 min and N-BOC-4-PIPERIDONE (10.0 g, 50.2 mmole, in 10 mL of anhydrous THF) BROMOACETONITRILE (4.2 mL, 60.2 mmole) and HMPA (20 mL) was added and the mixture stirred for an additional 2 h at RT. The reaction mixture was quenched with brine and concentrated in vacuo. The residue was taken up in ethyl acetate (500 mL) and washed with sat. NAHCO3 (2 x 200 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to obtain the title compound (7.0 g, 58percent) as a yellow oil : H NMR (400 MHz, CDCl3) 8 3.90 Hz (bs, 2H), 3.16 Hz (m, 2H), 2.55 Hz (s, 2H), 1.74 Hz (m, 2H), 1.50 (m, 2H), and 1.47 (s, 9H). LC-MS (ES) M/E 241.2 (M + H).
Reference: [1] Patent: WO2004/87145, 2004, A2, . Location in patent: Page/Page column 31-32
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