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[ CAS No. 433226-06-3 ] {[proInfo.proName]}

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Chemical Structure| 433226-06-3
Chemical Structure| 433226-06-3
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Product Details of [ 433226-06-3 ]

CAS No. :433226-06-3 MDL No. :MFCD08276943
Formula : C8H9BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QGADVECLXFPSOE-UHFFFAOYSA-N
M.W : 245.07 Pubchem ID :18525957
Synonyms :

Calculated chemistry of [ 433226-06-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.43
TPSA : 65.21 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) : -6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.09
Log Po/w (XLOGP3) : 1.97
Log Po/w (WLOGP) : 1.61
Log Po/w (MLOGP) : 1.22
Log Po/w (SILICOS-IT) : 1.5
Consensus Log Po/w : 1.68

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.74
Solubility : 0.442 mg/ml ; 0.0018 mol/l
Class : Soluble
Log S (Ali) : -2.96
Solubility : 0.266 mg/ml ; 0.00108 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.242 mg/ml ; 0.000989 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 433226-06-3 ]

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 [ 433226-06-3 ]

* 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 [ 433226-06-3 ]
  • Downstream synthetic route of [ 433226-06-3 ]

[ 433226-06-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 13362-26-0 ]
  • [ 433226-06-3 ]
YieldReaction ConditionsOperation in experiment
100% With N-Bromosuccinimide In tetrahydrofuran at 0 - 23℃; for 18 h; [0243] To a stirred solution of compound 11(15 g; 90.36 mmol; 1 eq) in dry THF (150 mL) was added NBS (16 g; 90.36 mmol; 1 eq) in portions at 0 °C and the resulting mixture was stirred at 23 °C for 18 h. The mixture was poured into ice-cold saturated aqueous NaHCO3 solution and the organic components were extracted with ethyl acetate (3 x 200 mL). The combined organic layers were then washed with brine solution, dried over anhydrous sodium sulfate, filtered and evaporated to dryness to afford the title compound (22 g, 100percent) as an off white solid. 1H NMR (DMSO-d6) ö 8.29 (d, 1H, J = 3 Hz), 8.12 (d, 1H, J = 2 Hz), 7.31 (s, 2H), 4.29 (q, 2H, J = 7 Hz), 1.30 (t, 3H, J = 7 Hz). LCMS: mlz = 245.0 [M+j, 247.0 [M+21, RT = 3.34 minutes, (Program P1, Column W).
98.36% With N-Bromosuccinimide In acetonitrile at 20℃; for 3 h; 100 mmol (16.6 g) of ethyl 2-aminonicotinate was reacted with 110 mmol (19.58 g) of N-bromosuccinimide in 200 ml of acetonitrile and reacted at room temperature for three hours. After the completion of the reaction allow to stand for three hours at zero degrees Celsius environment . Suction filtration carried out , filter cake leaching with acetonitrile to obtain 24. 1g of solid, the yield of 98.36percent. Acetonitrile spin recovery.
91% With bromine; sodium hydrogencarbonate In dichloromethane at 0℃; for 1 h; A CH2Cl2 (30 mL) solution of bromine (16.8Og, 105 mmol) was added to a CH2Cl2 (ISO mL) suspension of ethyl <2-aminonicotinate (11.64 g, 70 mmol) and NaHCO3 (17.7 g, 210 mmol) at 0 0C. After an hour stirring at this temperature, water (50 mL) was added. The solution was decolorized with a saturated solution OfNaHSO3, extracted with CH2Cl2, dried over MgSO4 and evaporated. Recrystallization from a CH2Cl2 /hexane mixture afforded 16.02 g (91percent) of the title compound. 1H NMR (300 MHz, CDCl3, δ) 8.22 (m, 2H), 4.35 (q, J=7.2 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H). MS (ESI) m/e 245 (M + H)+.
Reference: [1] Patent: WO2015/95128, 2015, A1, . Location in patent: Paragraph 0239; 0242; 0243
[2] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 236 - 246
[3] Patent: CN104402881, 2016, B, . Location in patent: Paragraph 0022; 0023
[4] Patent: WO2007/67416, 2007, A2, . Location in patent: Page/Page column 64; 134
  • 2
  • [ 14667-47-1 ]
  • [ 433226-06-3 ]
YieldReaction ConditionsOperation in experiment
99% With bromine; sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 1 h; To a stirred solution of 2-amino-nicotinic acid methyl ester (2 g, 13.15 mmol) and sodium bicarbonate (2.2 g, 26.31 mmol) in DCM (30 mL) is added a solution of bromine (1.01 mL in DCM (20 mL) drop wise at 0 °C. The reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is quenched with sodium bisulfite solution (50 mL) and extracted with DCM (2x40 mL). The combined organic layers are washed with brine (40 mL), dried over sodium sulphate, filtered, and evaporated under reduced pressure to give the title compound as a yellow solid (3 g, 99percent). LCMS m/z (79Br/81Br) 231/233 (M+H)+.
Reference: [1] Patent: WO2015/105786, 2015, A1, . Location in patent: Page/Page column 10
  • 3
  • [ 5345-47-1 ]
  • [ 433226-06-3 ]
Reference: [1] Patent: WO2015/95128, 2015, A1,
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