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[ CAS No. 17078-28-3 ] {[proInfo.proName]}

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Chemical Structure| 17078-28-3
Chemical Structure| 17078-28-3
Structure of 17078-28-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 17078-28-3 ]

CAS No. :17078-28-3 MDL No. :MFCD00075591
Formula : C10H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KQGHTOZUPICELS-UHFFFAOYSA-N
M.W : 179.22 Pubchem ID :152203
Synonyms :

Calculated chemistry of [ 17078-28-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.19
TPSA : 40.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.5
Log Po/w (XLOGP3) : 1.74
Log Po/w (WLOGP) : 1.38
Log Po/w (MLOGP) : 1.67
Log Po/w (SILICOS-IT) : 1.14
Consensus Log Po/w : 1.49

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.19
Solubility : 1.15 mg/ml ; 0.00644 mol/l
Class : Soluble
Log S (Ali) : -2.21
Solubility : 1.11 mg/ml ; 0.00619 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.93 mg/ml ; 0.00519 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.22

Safety of [ 17078-28-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17078-28-3 ]

* 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 [ 17078-28-3 ]
  • Downstream synthetic route of [ 17078-28-3 ]

[ 17078-28-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 17078-28-3 ]
  • [ 50438-75-0 ]
YieldReaction ConditionsOperation in experiment
90% With borane-THF In tetrahydrofuran at 0℃; for 5 h; As shown in Scheme 5, the bromide synthons used (41a-41c) were synthesized from the corresponding acids first by reduction to alcohols followed by bromination using PPh3/CBr4 (for 41a) or PPh3/Br2 (for 41b and 41c).; To a flame-dried, three-neck, 100 mL round-bottomed flask equipped with a condenser and argon line was added the appropriate carboxylic acid (10 mmol) dissolved in dry THF (25 mL). After cooling to 0°C, 1M BH3*THF (20 mmol) was added drop- wise to the stirred mixture and the reaction was then left at 0°C for 5h. The reaction mixture was diluted with cold water, washed with a saturated solution of NaHC03, and extracted with ethyl acetate (3 x 25 mL). The combined organic layers were washed with brine (1 x 25 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with 25percent ethyl acetate-hexanes to afford the corresponding alcohols. p- (N, N-dimethylamino) phenethyl Alcohol (40a). Yield, 90percent; mp. 56-57°C ;'H NMR (CDCl3) : 8 2.77 (t, 2H, J = 6.6 Hz), 2.92 (s, 6H, NMe2), 3.80 (t, 2H, J = 6.5 Hz), 6.72 (d, 2H, J = 8.53 Hz), 7.10 (d, 2H, J = 8.51 Hz). 13C NMR (CDC13) : 8 38.21, 40.93 (NMe2), 64.01, 113.20 (2C, Ar), 126.43 129.72 (2C, Ar), 149.51 ; IR (neat): 3284,2855, 1617, 1527, 1352,1049, 1021, 804. HRMS (ESI) m/z : Calcd for CloHlsNO [M+H] + 166.1232, found 166.1225 [M+H] +.
69% With borane-THF In tetrahydrofuran at 0 - 20℃; for 1 h; Inert atmosphere BH3.THF (5 mL, 1M in THF) was added dropwise into a mixture of 2-[4- (dimethylamino)phenyl] acetic acid (300 mg, 1.67 mmol) and tetrahydrofuran (10 mL) under nitrogen. The resulting solution was stirred for 1 h at room temperature. The reaction was then quenched by water, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1 :4) to afford the title compound (190 mg, 69percent) as a white solid. LCMS [M+H+] 166.
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 20, p. 4244 - 4258
[2] Patent: WO2003/95444, 2003, A1, . Location in patent: Page/Page column 22-23; 56
[3] Patent: WO2018/96159, 2018, A1, . Location in patent: Paragraph 0299-0302
[4] Tetrahedron, 2015, vol. 71, # 39, p. 7107 - 7123
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