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[ CAS No. 3279-90-1 ] {[proInfo.proName]}

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Chemical Structure| 3279-90-1
Chemical Structure| 3279-90-1
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Product Details of [ 3279-90-1 ]

CAS No. :3279-90-1 MDL No. :MFCD03839832
Formula : C9H8BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :MQWZSSIUHXNNTM-UHFFFAOYSA-N
M.W : 226.07 Pubchem ID :14373281
Synonyms :

Calculated chemistry of [ 3279-90-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.24
TPSA : 29.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.95
Log Po/w (XLOGP3) : 2.03
Log Po/w (WLOGP) : 1.76
Log Po/w (MLOGP) : 2.17
Log Po/w (SILICOS-IT) : 2.76
Consensus Log Po/w : 2.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.89
Solubility : 0.291 mg/ml ; 0.00129 mol/l
Class : Soluble
Log S (Ali) : -2.27
Solubility : 1.22 mg/ml ; 0.00538 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.03
Solubility : 0.0212 mg/ml ; 0.000094 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 3279-90-1 ]

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 [ 3279-90-1 ]

* 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 [ 3279-90-1 ]
  • Downstream synthetic route of [ 3279-90-1 ]

[ 3279-90-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 3279-90-1 ]
  • [ 1810-71-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 14, p. 1559 - 1562
  • 2
  • [ 3279-90-1 ]
  • [ 22190-35-8 ]
Reference: [1] Patent: US2004/220206, 2004, A1, . Location in patent: Page 24; 32
  • 3
  • [ 3279-90-1 ]
  • [ 70639-77-9 ]
Reference: [1] Patent: US2004/122001, 2004, A1,
  • 4
  • [ 34598-49-7 ]
  • [ 147497-32-3 ]
  • [ 3279-90-1 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With sodium azide; methanesulfonic acid In dichloromethane at 0 - 20℃;
Stage #2: With sodium hydroxide In dichloromethane; water at 0℃;
6-Bromo-3,4-dihvdroisoquinolin-l(2H)-one (1A):NaN3 (6.2 g, 94.78 mmol) was added to a solution of 5-bromo-l-indanone (10 g, 47.39 mmol) in 40 mL mixture of methane sulphonic acid and dichloromethane (1 : 1) in portion wise at 0 °C-5 °C. The resulting mixture was stirred for 8 h at room temperature. The reaction mixture was cooled to 0 °C in ice bath, neutralized with 5 percent aq. NaOH solution, and the aqueous layer with extracted with ethyl acetate (2x100 mL). The combined organic layer was washed with water and brine solution, dried over sodium sulphate, filtered and concentrated under vacuum. The residue was purified by silica gel flash column chromatography by eluting with 30 percent ethyl acetate in hexane to afford title compound (6.4 g, 60percent) as solid. 1H NMR (400 MHz, CDC13): δ 7.95 (d, J = 8.4 Hz, 1H), 7.5 (d, J = 8.4 Hz, 1H), 7.4 (s, 1H), 6.1 (bs, 1H), 3.6 (t, J = 6.8 Hz, 2H), 3.0 (t, J = 6.4 Hz, 2H).
60% With sodium azide; methanesulfonic acid In dichloromethane at 0 - 20℃; for 8 h; 2-(i -Oxo-6-(4-(3-(3-(trilluoromethyl)phenyl)ureido) phenyl)-3,4-dihydroisoquinolin-2(i H)-yl)acetic acid6-Hromo-3,4-dihydroisoquinolin-i (2H)-one (iA)Procedures:10443] NaN3 (6.2 g, 94.78 mmol) was added to a solution of5-bromo-i-indanone(iO g, 47.39 mmol) in 40 mL of mixture of methane sulphonic acid and dichloromethane (i : i) in portion wise at 00 C.-5° C. The resulting mixture was stirred for 8 h at room temperature. The reaction mixture was cooled to0°C. in ice bath, neutralized with 5percent aq. NaOH, and aqueous layer was extracted with ethyl acetate (2x1 00 mE). The combined organic layer was washed with water and brine solution, dried over Na2SO4 and filtered. The filtrate was concentrated under vacuum and purified by silica gel flash column chromatography using 30percent ethyl acetate in hexane to afford title compound (6.4 g, 60percent) as solid. ö ‘H NMR (400 MHz, CDC13): ö 7.95 (d, J=8.4 Hz, 1H), 7.5 (d, J=8.4 Hz, 1H), 7.4 (s, 1H), 6.1 (bs, 1H), 3.6 (t, J=6.8 Hz, 2
25% With sodium azide; methanesulfonic acid In chloroform at 0 - 10℃; for 2.5 h; Heating / reflux 5-Bromoindan-1-one (44 g, 209 mmol) was dissolved in CHCl3 (750 mL) with vigorous stirring and cooled to 0° C. Methanesulfonic acid (135 mL, 2090 mmol) was added dropwise. Sodium azide (40.7 g, 625 mmol) was added in portions over 30 min such that the internal temperature did not exceed 10° C. The reaction mixture was heated to reflux temperature and stirred for 2 h. The reaction mixture was cooled to room temperature and poured onto ice (1 kg) with manual stirring. The mixture was neutralized with NH4OH. The layers were separated. The organic solution was dried over MgSO4, filtered and concentrated in vacuo. Column chromatography (EtOAc) provided, after removal of solvent in vacuo: (1) 6-bromo-2H-1,2,3,4-quinol-1-one (10.7 g, 25percent yield): 1H NMR (CDCl3, 300 MHz): 8.11 (br s, 1H), 7.32 (d, 1H, J=1), 7.29 (dd, 1H, J=8, 1), 6.23 (br s, 1H), 6.25 (br s, 1H), 2.98 (t, 2H, J=7), 2.65 (t, 2H, J=7); MS (APCI+): 267, 269 (C11H12BrN2O, M++H+CH3CN) and (2) 6-bromo-1H-1,2,3,4-tetrahydroisoquinolone (21.5 g, 46percent yield): 1H NMR (CDCl3, 300 MHz): 7.95 (d, 1H, J=8), 7.51 (dd, 1H, J=8, 1), 7.21 (t, 1H, J=1), 6.25 (br s, 1H), 3.59 (t, 2H, J=7), 3.01 (t, 2H, J=7); MS (APCI+): 267, 269 (C11H12BrN2O, M++H+CH3CN).
Reference: [1] Patent: WO2012/162129, 2012, A1, . Location in patent: Page/Page column 35
[2] Patent: US2015/307445, 2015, A1, . Location in patent: Paragraph 0441; 0442; 0443
[3] Patent: US2006/63799, 2006, A1, . Location in patent: Page/Page column 9
  • 5
  • [ 3279-90-1 ]
  • [ 5292-43-3 ]
  • [ 1224927-63-2 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: With sodium hydride In N,N-dimethyl-formamide for 0.5 h; Inert atmosphere
Stage #2: at 20℃;
A.
Synthesis of tert-butyl 2-(6-bromo-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate
To a mixture of 95percent dry sodium hydride (834 mg, 33.0 mmol) in anhydrous N,N-dimethylformamide (30 mL) at room temperature was added a solution of 6-bromo-3,4-dihydroquinolin-2(1H)-one (6.780 g, 30.00 mmol) in anhydrous N,N-dimethylformamide (10 mL).
The reaction mixture was stirred for 30 minutes under an atmosphere of dry N2, followed by addition of a solution of tert-butyl 2-bromoacetate (7.5 mL, 49.7 mmol) in N,N-dimethylformamide (10 mL).
The reaction mixture was stirred at room temperature until the majority of the starting material was converted (confirmed by LCMS).
The reaction mixture was quenched with methanol (40 mL), the mixture concentrated under reduced pressure, then diluted with ethyl acetate (150 mL).
The organic phase was washed with water (100 mL), 30percent ammonium chloride (100 mL) and brine (100 mL), dried, and concentrated under reduced pressure.
Ethyl ether (20 mL) was added, and the mixture sonicated, filtered, washed with ether (20 mL), and dried to afford tert-butyl 2-(6-bromo-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate (7.348 g, 21.6 mmol, 72percent). LCMS mz 285.9 (M-56+H), 363.9 (M+Na), anal HPLC>97percent in purity. 1H NMR (400 MHz; CDCl3) δ 7.30-7.40 (m, 2H); 7.50-6.70 (m, 1H); 4.54 (s, 2H); 2.92 (m, 2H); 2.69 (m, 2H), 1.44 (s, 9H).
Reference: [1] Patent: US2010/113514, 2010, A1, . Location in patent: Page/Page column 17
  • 6
  • [ 3279-90-1 ]
  • [ 1427587-32-3 ]
Reference: [1] Patent: WO2013/37779, 2013, A1,
[2] Patent: WO2013/41591, 2013, A1,
[3] Patent: WO2014/139981, 2014, A1,
[4] Patent: US2016/9712, 2016, A1,
[5] Patent: WO2016/66662, 2016, A1,
[6] Patent: WO2016/66597, 2016, A1,
[7] Patent: US2013/72679, 2013, A1,
[8] Patent: US2013/79365, 2013, A1,
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