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[ CAS No. 59782-85-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 59782-85-3
Chemical Structure| 59782-85-3
Chemical Structure| 59782-85-3
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Product Details of [ 59782-85-3 ]

CAS No. :59782-85-3 MDL No. :MFCD01861979
Formula : C6H3Cl2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :SXQSMLIMBNMUNB-UHFFFAOYSA-N
M.W : 192.00 Pubchem ID :2736085
Synonyms :

Calculated chemistry of [ 59782-85-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.22
TPSA : 50.19 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) : -6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.17
Log Po/w (XLOGP3) : 2.01
Log Po/w (WLOGP) : 2.09
Log Po/w (MLOGP) : 0.09
Log Po/w (SILICOS-IT) : 2.04
Consensus Log Po/w : 1.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.63
Solubility : 0.446 mg/ml ; 0.00232 mol/l
Class : Soluble
Log S (Ali) : -2.69
Solubility : 0.391 mg/ml ; 0.00204 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.63
Solubility : 0.446 mg/ml ; 0.00232 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 59782-85-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 59782-85-3 ]

* 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 [ 59782-85-3 ]
  • Downstream synthetic route of [ 59782-85-3 ]

[ 59782-85-3 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 59782-85-3 ]
  • [ 126954-66-3 ]
Reference: [1] Patent: CN108276401, 2018, A,
[2] Patent: WO2018/127096, 2018, A1,
[3] Patent: CN108727369, 2018, A,
  • 2
  • [ 67-56-1 ]
  • [ 59782-85-3 ]
  • [ 67754-03-4 ]
YieldReaction ConditionsOperation in experiment
97% at 0 - 20℃; for 25.5 h; Piperazine A37 may be used in place of piperazine or a substituted piperazine in the above examples. Lithium 2-amino-5-chloronicotinateA solution of 2,5-dichloronicotinic acid (20.2 g, 0.105 mol) in methanol (500 mL) was cooled to 00C and neat thionyl chloride (38 mL, 63 g, 0.525 mol) was added over -30 min. The reaction mixture was stirred at O0C for 1 hour. The cooling bath was removed, the reaction temperature was allowed to warm to room temperature, and the reaction was allowed to stir for an additional 2 days at room temperature. The solvent was removed under reduced pressure to give an off-white residue. The residue was dissolved in Et2O (-500 mL) and the resulting solution was washed successively with saturated aqueous NaHCO3 solution (-300 mL), water (-300 mL), and brine (-300 mL). The organic layer was separated, dried over anhydrous MgSO4, and filtered. Removal of the solvent under reduced pressure yielded methyl 2,5-dichloronicotinate (21.0 g, 97percent) as a white solid. EPO <DP n="128"/>Performed in duplicate on identical scales in two pressure vessels, methyl 2,5-dichloronicotinate (4.5 g, 22 mmol) was dissolved in ammonia solution (250 mL, 0.5 M in 1,4-dioxane; 0.125 mol). The pressure vessels were sealed and heated at (85 +/- 5) 0C for 9 days. The two reaction mixtures were allowed to cool to room temperature, then combined and concentrated under reduced pressure to yield a white solid. Dissolution of the solid in 1 :1 acetone-MeOH (-500 mL), followed by adsorption onto silica gel (25 g) and then purification by flash column chromatography (25:10:1 hexane-CH2CI2- Et2O), gave 6.08 g (75percent) of methyl 2-amino-5-chloronicotinate. A solution of LiOH*H2O (1.38 g, 33 mmol) in water (33 mL) was added in one portion to a suspension of methyl 2-amino~5~chloronicotinate (6.08 g, 27 mmol) in MeOH (110 mL). The reaction mixture was stirred at 7O0C for 24 hours, and gradually became homogeneous. The solvents were removed under reduced pressure, and after the resulting white solid was dried under vacuum (<1 mmHg) to constant weight, 5.51 g (95percent) of lithium 2-amino-5-ch.oronicotinate was obtained.
97%
Stage #1: at 0 - 20℃; for 49.5 h;
Stage #2: With water; sodium hydrogencarbonate In diethyl ether
Lithium 2-amino-5-chloronicotinateA solution of 2,5-dichloronicotinic acid (20.2 g, 0.105 mol) in methanol (500 ml_) was cooled to 00C and neat thionyl chloride (38 mL, 63 g, 0.525 mol) was added over -30 min. The reaction mixture was stirred at 00C for 1 hour. The cooling bath was removed, the reaction temperature was allowed to warm to room temperature, and the reaction was allowed to stir for an additional 2 days at room temperature. The solvent was removed under reduced pressure to give an off-white residue. The residue was dissolved in Et2O (-500 mL) and the resulting solution was washed successively with satd. aq. NaHCO3 solution (-300 mL), water (-300 mL), and brine (-300 mL). The organic layer was separated, dried over anhydrous MgSO4, and filtered. Removal of the solvent under reduced pressure yielded methyl 2,5-dichloronicotinate (21.0 g, 97percent) as a white solid.
97%
Stage #1: at 0 - 20℃; for 49.5 h;
Stage #2: With sodium hydrogencarbonate In diethyl ether; water
Lithium 2-amino-5-chloronicotinateA solution of 2,5-dichloronicotinic acid (20.2 g, 0.105 mol) in methanol (500 mL) was cooled to 0°C and neat thionyl chloride (38 mL, 63 g, 0.525 mol) was added over -30 min. The reaction mixture was stirred at 0°C for 1 hour. The cooling bath was removed, the reaction temperature was allowed to warm to rt, and the reaction was allowed to stir for an additional 2 days at room temperature and the solvent was removed under reduced pressure to give an off-white residue. The residue was dissolved in Et2O (-500 mL) and the resulting solution was washed successively with saturated aqueous EPO <DP n="121"/>NaHCO3 solution (-300 imL), water (-300 mL), and brine (-300 mL). The organic layer was separated, dried over anhydrous MgSO4, and filtered. Removal of the solvent under reduced pressure yielded methyl 2,5-dichloronicotinate (21.0 g, 97percent) as a white solid.
97% at 0 - 20℃; for 49.5 h; A solution of 2,5-dichloronicotinic acid A54 (20.2 g, 0.105 mol) in methanol (500 mL) was cooled to 00C and neat thionyl chloride (38 mL, 63 g, 0.525 mol) was added over -30 min. The reaction mixture was stirred at 0°C for 1 hour. The cooling bath was removed, the reaction temperature was allowed to warm to rt, and the reaction was allowed to stir for an additional 2 days at room temperature and the solvent was removed under reduced pressure to give an off-white residue. The residue was dissolved in Et.2ψ (-500 mL) and the resulting solution was washed successively with saturated aqueous NaHCO3 solution (-300 mL), water (-300 mL), and brine (-300 mL). The organic layer was separated, dried over anhydrous MgSO4, and filtered. Removal of the solvent under reduced pressure yielded methyl 2,5-dichloronicotinate (21.0 g, 97percent) as a white solid.Performed in duplicate on identical scales in two pressure vessels, methyl 2,5-dichloronicotinate (4.5 g, 22 mmol) was dissolved in ammonia solution (250 mL, 0.5 M in 1 ,4-dioxane; 0.125 mol). The pressure vessels were sealed and heated at (85 +/- 5) 0C for 9 days. The two reaction mixtures were allowed to cool to room temperature, then combined and concentrated under reduced pressure to yield a white solid. Dissolution of the solid in 1 :1 acetone-MeOH (-500 mL), followed by adsorption onto silica gel (25 g) and <n="101"/>then purification by flash column chromatography (25:10:1 hexane-C H2CI2- Et2O), gave 6.08 g (75percent) of methyl 2-amino-5-chloronicotinate.A solution of LiOHH2O (1.38 g, 33 mmol) in water (33 mL) was added in one portion to a suspension of methyl 2-amino-5-chloronicotinate (6.08 g, 27 mmol) in MeOH (110 mL). The reaction mixture was stirred at 700C for 24 hours, and gradually became homogeneous. The solvents were removed under reduced pressure, and after the resulting white solid was dried under vacuum (<1 mmHg) to constant weight, 5.51 g (95percent) of lithium 2-amino-5-chloronicotinate A55 was obtained.
92%
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 18 h;
Stage #2: at 0℃; for 0.5 h;
A solution of 2,5-dichloronicotinic acid (25.0 g, 130 mmol) in methylene chloride (650 mL) was treated with oxalyl chloride (22 mL, 260 mmol) followed by N,N- dimethylformamide (1.0 mL) and stirred at room temperature for 18 hours. The gas evolution ceased and the reaction mixture was concentrated. The acid chloride intermediate was taken up in methylene chloride (300 mL), cooled to 0 °C and treated with methanol (26 mL). The reaction was stirred at 0 °C for 30 minutes, allowed to warm to room temperature and was concentrated in vacuo to give an oil. This oil was taken up in ethyl acetate, washed with water saturated potassium carbonate, brine, dried over magnesium sulfate and concentrated to give methyl 2,5-dichloronicotinate (24.5 g, 92percent) as an oil. LCMS calculated for C7H6CI2 O2 (M+H)+: m/z = 205.9, 207.9; found: 205.9, 207.9
90%
Stage #1: With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide
Stage #2: at 0℃; for 0.5 h;
A solution of 2,5-dichloronicotinic acid (20.0 g, 104 mmol, OChem) in DCM (520 mL) was treated with oxalyl chloride (26. mL, 310 mmol) followed by DMF (0.015 mL, 0.19 mmol). The reaction was stirred overnight. The reaction mixture was then concentrated in vacuo. The acid chloride was diluted with DCM (200 mL), cooled to 0° C. and treated with MeOH (110 mL). After stirring for 30 minutes, solvents were removed in vacuo. The crude residue was dissolved in DCM and washed sequentially with saturated NaHCO3 solution, water, and saturated NaCl solution. The organic layer was dried over Na2SO4, filtered, and concentrated to afford a white crystalline solid that was used without further purification. Yield: 18.8 g, 90percent. LCMS calculated for C7H6Cl2NO2 (M+H)+: m/z=206.0; found: 206.0.

Reference: [1] Patent: WO2006/88840, 2006, A1, . Location in patent: Page/Page column 126-127
[2] Patent: WO2006/91428, 2006, A2, . Location in patent: Page/Page column 124
[3] Patent: WO2006/88837, 2006, A2, . Location in patent: Page/Page column 119-120
[4] Patent: WO2007/109238, 2007, A1, . Location in patent: Page/Page column 99-100
[5] Patent: WO2011/130342, 2011, A1, . Location in patent: Page/Page column 90
[6] Patent: US2017/129899, 2017, A1, . Location in patent: Paragraph 0626; 0627
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YieldReaction ConditionsOperation in experiment
87% at 0 - 20℃; for 1 h; 2,5-Dichloronicotine acid (2150.0 mg, 11.20 mmol) was dissolved in mixture solution of DCM (10.0 mL) and MeOH (5.0 mL), and trimethylsilyldiazomethane (2.0M in hexane) (11.2 mL, 22.40 mmol) was slowly added thereto at 0° C. The reaction mixture was stirred at room temperature for one hour and then distilled under reduced pressure. The residue was purified by column chromatography (EtOAc:n-Hex=1:9) on silica. The fractions containing the product were collected and evaporated to obtain white solid compound of methyl 2,5-dichloronicotinate (2020.0 mg, 87percent). [1031] LCMS ESI (+): 206 (M+1) [1032] 1H-NMR (300 MHz, CDCl3); δ: 8.48 (d, 1H, J=2.6 Hz), 8.16 (d, 1H, J=2.6 Hz), 3.98 (s, 3H)
Reference: [1] Patent: US2014/315888, 2014, A1, . Location in patent: Paragraph 1030-1032
  • 4
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Reference: [1] Journal of Chemical & Engineering Data, 1981, vol. 26, # 3, p. 332 - 333
  • 5
  • [ 186581-53-3 ]
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Reference: [1] Journal of Chemical & Engineering Data, 1981, vol. 26, # 3, p. 332 - 333
  • 6
  • [ 2402-78-0 ]
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Reference: [1] Patent: EP1364950, 2003, A1, . Location in patent: Page/Page column 39
  • 7
  • [ 138006-41-4 ]
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Reference: [1] Patent: EP634413, 1995, A1,
  • 8
  • [ 38076-80-1 ]
  • [ 59782-85-3 ]
Reference: [1] Synthetic Communications, 1989, vol. 19, # 3and4, p. 553 - 560
  • 9
  • [ 609-71-2 ]
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Reference: [1] Synthetic Communications, 1989, vol. 19, # 3and4, p. 553 - 560
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  • [ 868636-76-4 ]
Reference: [1] Patent: WO2005/102389, 2005, A2,
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