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[ CAS No. 878207-92-2 ] {[proInfo.proName]}

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Chemical Structure| 878207-92-2
Chemical Structure| 878207-92-2
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Product Details of [ 878207-92-2 ]

CAS No. :878207-92-2 MDL No. :MFCD12756112
Formula : C8H8ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XWPSWOKQWBNRDW-UHFFFAOYSA-N
M.W : 185.61 Pubchem ID :45489870
Synonyms :

Calculated chemistry of [ 878207-92-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.49
TPSA : 39.19 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) : -5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.04
Log Po/w (XLOGP3) : 2.36
Log Po/w (WLOGP) : 1.83
Log Po/w (MLOGP) : 1.25
Log Po/w (SILICOS-IT) : 2.29
Consensus Log Po/w : 1.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.72
Solubility : 0.357 mg/ml ; 0.00193 mol/l
Class : Soluble
Log S (Ali) : -2.82
Solubility : 0.279 mg/ml ; 0.0015 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.1
Solubility : 0.146 mg/ml ; 0.000785 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.89

Safety of [ 878207-92-2 ]

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 [ 878207-92-2 ]

* 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 [ 878207-92-2 ]
  • Downstream synthetic route of [ 878207-92-2 ]

[ 878207-92-2 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 878207-91-1 ]
  • [ 878207-92-2 ]
YieldReaction ConditionsOperation in experiment
41% at 110℃; for 4 h; A solution of 2-(methoxycarbonyl)-3-methylpyridin-1-ium-1-olate (500 mg, 2.99 mmol, 1.00 equiv) in phosphorus oxychloride (2 mL) was stirred for 4 hours at 110° C.
The reaction was quenched with water, adjusted pH to 7, and extracted with ethyl acetate.
The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under vacuum.
The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:5) to give the title compound (230 mg, 41percent) as a white solid. LC-MS (ES, m/z): 186 [M+H]+.
40% With trichlorophosphate In 1,2-dichloro-ethane for 4 h; Reflux A solution of 2-(methoxycarbonyl)-3-methylpyridine 1-oxide (500 mg, 2.99 mmol) and phosphorus oxychloride (0.55 mL, 5.98 mmol) in 1,2-dichloroethane (10 ml) was refluxed for 4 h. After completion of reaction, the reaction mixture was combined with 100 ml of ice water and extracted with dichoromethane (50 ml x 2) being washed with water and sodium bicarbonate solution, and then the combined organic layer was dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure, and the resulting residue was purified by silica gel column chromatography (10percent EA/Hexnae) to give 223 mg (yield 40percent) of the title compound. 1H NMR(300MHz, CDCl3) δ 7.59 (dd, J = 8.1, 0.5 Hz, 1H), 7.38 (d, J = 8.1 Hz, 1H), 3.97 (s, 3H), 2.57 (s, 3H).
37% at 100℃; for 3 h; A solution of 2-(methoxycarbonyl)-3-methylpyridine 1-oxide (2 g, 6.0 mmol) in POCI3 (5 mL) was stirred at 100°C for 3 hours. After being concentrated, the residue was purified by column chromatography (PE : EtOAc = 1 : 1) to give the product of methyl 6-chloro- 3-methylpicolinate (380 mg, yield: 37percent). -NMR (CDCI3, 400 MHz) δ 7.59 (d, J= 8.0 Hz, 1H), 7.38 (d, J= 8.0 Hz, 1H), 3.96 (s, 3H), 2.56 (s, 3H). MS (M+H)+: 186 / 188.
37% at 100℃; for 3 h; solution of 2-(methoxycarbonyl)-3-methylpyridine 1-oxide (2 g, 6.0 mmol) in POd3 (5 mL) was stirred at 100°C for 3 hours. After being concentrated, the residue was purified by column chromatography (PE : EtOAc = 1: 1) to give the product of methyl 6-chloro-3- methylpicolinate (380 mg, yield: 37percent). ‘H-NMR (CDC13, 400 MHz) 7.59 (d, J 8.0 Hz, 1H),7.38 (d, J= 8.0 Hz, 1H), 3.96 (s, 3H), 2.56 (s, 3H). MS (M+H): 186 / 188.
20.9% at 0 - 20℃; for 16.75 h; POCl3 (30.0 mL) is added slowly to methyl 3 -methyl- 1 -oxido- pyridin- l-ium-2-carboxylate (13.0 g, 0.077 mol) at 0 °C over 30 minutes. The reaction mixture is stirred for 15 minutes at 0 °C and then gradually warmed to ambient temperature. After 16 hours, the reaction mixture is cooled to 0 °C and excess POCl3 is removed under reduced pressure. The crude residue is then quenched by addition of ice and diluted with water and CH2CI2 (50 mL). The organic layer is washed sequentially with saturated NaHC03 solution, water, and brine; dried over sodium sulfate; filtered; and concentrated under reduced pressure. The crude product is purified by silica gel flash chromatography, eluting 5-10percent EtOAc in hexanes to afford methyl 6-chloro-3 -methyl - pyridine-2-carboxylate as a white solid (3.00 g, 20.9percent). Mass spectrum (m/z): 186.2 (M+H)+.

Reference: [1] Patent: US2015/57260, 2015, A1, . Location in patent: Paragraph 1234; 1235
[2] Patent: WO2015/25026, 2015, A1, . Location in patent: Page/Page column 268
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 6, p. 1736 - 1739
[4] Patent: WO2014/209727, 2014, A1, . Location in patent: Page/Page column 69
[5] Patent: WO2014/205593, 2014, A1, . Location in patent: Page/Page column 73
[6] Patent: WO2015/94912, 2015, A1, . Location in patent: Page/Page column 11-12
[7] Patent: WO2006/25783, 2006, A1, . Location in patent: Page/Page column 153
  • 2
  • [ 1201924-32-4 ]
  • [ 18107-18-1 ]
  • [ 878207-92-2 ]
Reference: [1] Patent: WO2009/155156, 2009, A1, . Location in patent: Page/Page column 63
  • 3
  • [ 59718-84-2 ]
  • [ 878207-92-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 6, p. 1736 - 1739
[2] Patent: WO2014/209727, 2014, A1,
[3] Patent: WO2014/205593, 2014, A1,
[4] Patent: US2015/57260, 2015, A1,
[5] Patent: WO2015/25026, 2015, A1,
[6] Patent: WO2015/94912, 2015, A1,
  • 4
  • [ 20970-75-6 ]
  • [ 878207-92-2 ]
Reference: [1] Patent: WO2009/155156, 2009, A1,
  • 5
  • [ 159727-88-5 ]
  • [ 878207-92-2 ]
Reference: [1] Patent: WO2009/155156, 2009, A1,
  • 6
  • [ 1201924-31-3 ]
  • [ 878207-92-2 ]
Reference: [1] Patent: WO2009/155156, 2009, A1,
  • 7
  • [ 878207-92-2 ]
  • [ 1201924-32-4 ]
YieldReaction ConditionsOperation in experiment
97% With water; sodium hydroxide In tetrahydrofuran at 0 - 50℃; for 2 h; A solution of aqueous 2N NaOH (5 ml) is added to a stirred solution of methyl 6-chloro-3-methyl-pyridine-2-carboxylate (0.500 g, 2.702 mmol) in THF (10 mL) at 0 °C. The mixture is heated at 50°C for 2 hours. The reaction mixture is acidified with aqueous citric acid solution and extracted with EtOAc (2 x 10 ml). The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound as an off-white solid (0.45 g, 97percent). The residue is used in next step without further purification. Mass spectrum (m/z): 172.0 (M+H)+.
84% With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 3 h; Scheme 1, step A. A solution of aqueous IN NaOH (10 ml) is added to a stirred solution ofmethyl6-chloro-3-methyl-pyridine-2-carboxylate (1.0 g, 5.39 mmoles) inTHF:MeOH (IOml:2 ml). The mixture is stirred at room temperature for 3 hours. Theorganic solvent is removed under reduced pressure and the semi-solid is dissolved inwater and acidified to pH I-2 with aqueous IN HCI. The resulting precipitate is filtered,washed with water, and dried at 40°C in a vacuum oven for I2 hours to give the title compound as a white solid (780 mg, 84percent). Mass spectrum (m/z): I72.0 (M+I).
Reference: [1] Patent: WO2015/94912, 2015, A1, . Location in patent: Page/Page column 12
[2] Patent: WO2014/4230, 2014, A1, . Location in patent: Page/Page column 8; 45
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