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[ CAS No. 321601-48-3 ] {[proInfo.proName]}

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Chemical Structure| 321601-48-3
Chemical Structure| 321601-48-3
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Product Details of [ 321601-48-3 ]

CAS No. :321601-48-3 MDL No. :MFCD12828055
Formula : C7H6BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :UGFPNFKMYRHGBG-UHFFFAOYSA-N
M.W :232.03 Pubchem ID :22175135
Synonyms :

Calculated chemistry of [ 321601-48-3 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.24
TPSA : 59.42 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) : -6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.16
Log Po/w (XLOGP3) : 2.26
Log Po/w (WLOGP) : 1.34
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : 1.41
Consensus Log Po/w : 1.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.94
Solubility : 0.266 mg/ml ; 0.00115 mol/l
Class : Soluble
Log S (Ali) : -3.14
Solubility : 0.166 mg/ml ; 0.000717 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.39
Solubility : 0.954 mg/ml ; 0.00411 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 321601-48-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 321601-48-3 ]

* 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 [ 321601-48-3 ]
  • Downstream synthetic route of [ 321601-48-3 ]

[ 321601-48-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 62733-99-7 ]
  • [ 321601-48-3 ]
  • [ 321596-58-1 ]
Reference: [1] Patent: EP1516874, 2015, B1,
  • 2
  • [ 321601-48-3 ]
  • [ 1256810-26-0 ]
Reference: [1] Patent: WO2014/121418, 2014, A1,
[2] Patent: WO2014/209727, 2014, A1,
[3] Patent: WO2014/205593, 2014, A1,
  • 3
  • [ 321601-48-3 ]
  • [ 74-88-4 ]
  • [ 945954-94-9 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 3 h; A mixture of methyl 6-bromo-3-hydroxypicolinate (4 g, 17.2 mmol), CH3I (7.15 g, 34.5 mmol) and K2C03 (4.76 g, 34.5 mmol) in DMF (50 mL) was stirred at RT for 3 hours. After concentrated, the mixture was diluted with H20 and extracted with EtOAc (50 mL * 3). The organic layer was dried over Na2S04 and concentrated to give crude methyl 6-bromo-3- methoxypicolinate (4 g, yield: 90percent). 1H- MR (CDC13 , 400 MHz) δ 7.56 (d, J= 8.0 Hz, 1H), 7.25 (d, J= 8.0 Hz, 1H), 3.94 (s, 3H), 3.90 (s, 3H). MS (M+H)+: 256 / 258.
78% With potassium carbonate In acetone for 3 h; Reflux [0183] Methyl 6-bromo-3-hydroxypicolinate (5.07 g, 21.85 mmol) was dissolved in acetone (75 mL).
To the resulting solution were added dropwise potassium carbonate (K2CO3) (4.83 g, 34.96 mmol) and iodomethane (CH3I) (1.77 mL, 28.41 mmol) and the solution was refluxed with heat for 3 hrs.
The solution was evaporated under reduced pressure to concentrate, diluted with EtOAc, and washed with water.
The washed organic solvent was dried over anhydrous magnesium sulfate (MgSO4) to concentrate.
The resulting residue was isolated and purified by silica gel column chromatography (hexane/ethylacetate = 3/1) to give the white title compound (4.18 g, 78 percent).
1H NMR (600 MHz, CDCl3) δ 7.57 (d, J = 9.0 Hz, 1H), 7.26 (d, J = 9.0 Hz, 1H), 3.95 (s, 3H), 3.92 (s, 3H).
76% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4 h; (step 3 ); A solution of the compound obtained in step 2 (9.42 g) , methyl iodide (2.78 mL) and potassium carbonate (7.29 g) in DMF (80 mL) was stirred at room temperature for 4 hrs, and poured into cold water. The mixture was extracted twice with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 20-25percent ethyl acetate/hexane) and <n="86"/>crystallized from ethyl acetate/hexane to give methyl 6-bromo-3-methoxypyridine-2-carboxylate (7.57 g, 76percent) as white crystals,
42% With potassium carbonate In N,N-dimethyl-formamide at 20℃; A mixture of methyl 6-bromo-3-hydroxypicolinate (10.0 g, 43.10 mmol), Mel (12.3 g, 86.66 mmol) and K2C03 (12.0 g, 86.83 mmol) in DMF (100 mL) was stirred at RT overnight. Then the reaction mixture was concentrated, diluted with water and extracted with EtOAc. The organic layer was dried over a2S04 and concentrated to give methyl 6-bromo-3- methoxypicolinate (4.5 g, yield 42percent). XH-NMR (CDC13, 400 MHz) δ 7.55 (d, J = 8.8 Hz, 1H), 7.24 (d, J = 8.8 Hz, 1H), 3.94 (s, 3H), 3.90 (s, 3H). MS (M+H)+: 246 / 248.
42% With potassium carbonate In N,N-dimethyl-formamide at 25℃; A mixture of methyl 6-bromo-3-hydroxypicolinate (10.0 g, 43.10 mmol), Mel (12.3 g, 86.66 mmol) and K2C03 (12.0 g, 86.83 mmol) in DMF (100 mL) was stirred at RT overnight. Then the reaction mixture was concentrated, diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to give methyl 6-bromo-3-methoxypicolinate (4.5 g,yield 42percent). ‘H-NMR (CDC13, 400 MHz) 7.55 (d, J = 8.8 Hz, 1H), 7.24 (d, J = 8.8 Hz, 1H), 3.94(s, 3H), 3.90 (s, 3H). MS (M+H): 246 / 248.

Reference: [1] Patent: WO2014/121418, 2014, A1, . Location in patent: Page/Page column 45
[2] Patent: EP3255042, 2017, A2, . Location in patent: Paragraph 0180; 0183
[3] Patent: WO2007/89031, 2007, A1, . Location in patent: Page/Page column 84-85
[4] Patent: WO2014/209727, 2014, A1, . Location in patent: Page/Page column 39
[5] Patent: WO2014/205593, 2014, A1, . Location in patent: Page/Page column 41; 42
  • 4
  • [ 186581-53-3 ]
  • [ 321601-48-3 ]
  • [ 945954-94-9 ]
Reference: [1] Patent: WO2007/31558, 2007, A1, . Location in patent: Page/Page column 33
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