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[ CAS No. 15855-06-8 ] {[proInfo.proName]}

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Chemical Structure| 15855-06-8
Chemical Structure| 15855-06-8
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Product Details of [ 15855-06-8 ]

CAS No. :15855-06-8 MDL No. :MFCD00173928
Formula : C7H6ClNO3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :PJQBTHQTVJMCFX-UHFFFAOYSA-N
M.W : 187.58 Pubchem ID :2782124
Synonyms :

Calculated chemistry of [ 15855-06-8 ]      Expand+

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 : 42.7
TPSA : 59.42 ?2

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) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.35
Log Po/w (XLOGP3) : 1.64
Log Po/w (WLOGP) : 1.44
Log Po/w (MLOGP) : -0.36
Log Po/w (SILICOS-IT) : 1.37
Consensus Log Po/w : 1.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.27
Solubility : 0.998 mg/ml ; 0.00532 mol/l
Class : Soluble
Log S (Ali) : -2.5
Solubility : 0.592 mg/ml ; 0.00316 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.14
Solubility : 1.35 mg/ml ; 0.00718 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.94

Safety of [ 15855-06-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 15855-06-8 ]

* 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.

  • Downstream synthetic route of [ 15855-06-8 ]

[ 15855-06-8 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 15855-06-8 ]
  • [ 64-17-5 ]
  • [ 106719-08-8 ]
YieldReaction ConditionsOperation in experiment
Sulfuric acid (1 ml_) is added to a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (4.16 g, 22.2 mmol) in ethanol (20 ml_). The clear solution is stirred at 700C for 18 h. The mixutre is neutralised by adding sat. aq. NaHCO3 solution and then extracted three times with EA (3x250 ml_). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give 2-chloro-6-methoxy- isonicotinic acid ethyl ester (4.32 g) as a white solid; LC-MS: tR = 1.00 min, [M+1]+ = 215.89.
a) Sulfuric acid (1 mL) is added to a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (4.16 g, 22.2 mmol) in ethanol (20 mL). The clear solution is stirred at 70 C. for 18 h. The mixture is neutralised by adding sat. aq. NaHCO3 solution and then extracted three times with EA (3*250 mL). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> ethyl ester (4.32 g) as a white solid; LC-MS: tR=1.00 min, [M+1]+=215.89.
With sulfuric acid; at 70℃; for 18h; a) Sulfuric acid (1 mL) is added to a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (4.16 g, 22.2 mmol) in ethanol (20 mL). The clear solution is stirred at 70 C. for 18 h. The mixture is neutralised by adding sat. aq. NaHCO3 solution and then extracted three times with EA (3*250 mL). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> ethyl ester (4.32 g) as a white solid; LC-MS: tR=1.00 min, [M+1]+=215.89.
3.205 g With thionyl chloride; In toluene; at 0 - 20℃; for 24h; Step 1 : Ethyl 2-chloro-6-methoxyisonicotinate To a previously sonicated suspension of <strong>[15855-06-8]2-chloro-6-methoxyisonicotinic acid</strong> (4.0g, 21 mmol) in ethanol (50 ml.) was added thionyl chloride (4.64 ml_, 64.0 mmol) at 0C. The reaction mixture was stirred at 0C for 2 h and then at room temperature for 18h. Thionyl chloride (4.64 ml_, 64.0 mmol) was slowly added and the mixture was stirred at room temperature for 4 h. The reaction mixture was quenched by slowly pouring into a saturated aqueous solution of sodium bicarbonate (200 ml_). Ice was added to the mixture to lower the temperature. The mixture was extracted with diethyl ether (150 ml_ x2). The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford a clear syrup as crude product. The crude product was dried for 2 h under high vacuum while heating to 80C. The resulting residue was concentrated from toluene (500 ml.) to afford ethyl 2-chloro-6- methoxyisonicotinate as an off white solid (3.205 g). 1H NMR (400 MHz, CDCI3) delta 1.40 (s, 3H), 3.98 (s, 3H), 4.39 (s, 2H), 7.22 (s, 1 H), 7.44 (s, 1 H).
Sulfuric acid (1 mL) is added to a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (4.16 g, 22.2 mmol) in ethanol (20 mL). The clear solution is stirred at 700C for 18 h. The mixutre is neutralised by adding sat. aq. NaHCO3 solution and then extracted three times with EA (3x250 mL). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> ethyl ester (4.32 g) as a white solid; LC-MS: tR = 1.00 min, [M+1]+ = 215.89.

  • 2
  • [ 15855-06-8 ]
  • [ 105596-63-2 ]
YieldReaction ConditionsOperation in experiment
78% With hydrogen; triethylamine;palladium 10% on activated carbon; In methanol; at 20℃; under 155.149 Torr; To a suspension of the title compound of Preparation 22 (1.94 g, 6.49 mmol) in acetonitrile (150 mL), sodium iodide (4.90 g, 32.69 mmol) and trimethylsilyl chloride (4.10 mL, 32.42 mmol) were added. The resulting suspension was stirred under nitrogen atmosphere at 400C for 3 days. The mixture was cooled to O0C and the solid was filtered off, washed with acetonitrile and dried to yield 1.66 g (90%) of the title compound.LRMS: m/z 285(M+1 )+ Retention time: 2.86min (method B)
  • 3
  • [ 124-41-4 ]
  • [ 5398-44-7 ]
  • [ 15855-06-8 ]
YieldReaction ConditionsOperation in experiment
82% In methanol; for 24h;Heating / reflux; Freshly prepared sodium methoxide (from 1.5 g sodium in 15 mL dry methanol) was added dropwise to a solution of Example 16 (5.0 g, 26 mmol) in dry methanol (25 mL). The reaction mixture was refluxed for 24 h, allowed to cool to RT and poured in aqueous HCl (10%, 100 mL). A pinkish solid separated and was collected on a filter, washed with water and air-dried (4.0 g, 82%). IH NMR (400 MHz, DMSO-d6) 5 3.89 (s, 3H) 7.17 (s, 1H) 7.39 (s, 1H) 13.96 (br s, OH).
81% In methanol; for 24h;Reflux; 200 mL of a25% solution of sodium methoxide in methanol was added on a solution of 10.3 g (53.6 mmol) of 2,6-dichloropyridine-4-carboxylic acid (1) in100 mL of methanol and refluxed for 24 h. The mixture was cooled toroom temperature, filtered off and evaporated. The solid was dissolvedin water, acidified with 2 N HCl and extracted with ethyl acetate. Theorganic phase was dried over anhydrous Na2SO4, filtered andevaporated, to obtain 8.1 g (43.2 mmol, 81%) of 2-chloro-6-methoxypyridine-4-carboxylic acid (2) as a brown amorphous solid.1H NMR (200 MHz, CD3OD): 3.87 (3H, s), 7.15 (1H, s), 7.36 (1H, s). 13CNMR (50 MHz, CD3OD): 54.5 (CH3), 109.4 (CH), 115.5 (CH), 144.3 (C),148.1 (C), 164.1 (C), 164.6 (C).
  • 6
  • [ 15855-06-8 ]
  • [ 193001-91-1 ]
YieldReaction ConditionsOperation in experiment
42% BH3. DMS (1.0 mL, 10.66 mmol) was refluxed in THF (20 mL) for 30 min (formation of BH3. THF). At RT, Example 17 (2.0 g, 10.66 mmol in 10 mL THF) was added dropwise, and then the reaction mixture was heated to reflux for 3 h. The solution was allowed to cool to ambient temperature, solid sodium carbonate (0.5 g) and water (5 mL). The resulting mixture was heated for a short while and poored in water (50 mL). Extraction with ethyl acetate (3 x 50 mL), drying of the combined organic layers (Na2SO4) and evaporation in vacuo gave a 1: 1 mixture of starting material and product. Purification by flash column chromatography over silica gel eluting with ethyl acetate gave 780 mg (42 %) of an off-white solid. IH NMR (400 MHz, CDC13) 8 3.92 (s, 3H) 4.66 (s, 2H) 6.64 (s, 1H) 6.89 (s, 1H).
2 g With borane-THF; In tetrahydrofuran; at 0 - 20℃; for 20.5h;Inert atmosphere; To a solution of 2-chloro-6-methoxyisonicotinic acid (2.5 g) in dry tetrahydrofuran (50 ml) at 0C under nitrogen was added dropwise a solution of borane- tetrahydrofuran complex (1.0M solution in tetrahydrofuran; 40 ml) over fifteen minutes. After the addition was complete, the cooling bath was removed and the mixture allowed to warm to room temperature. After three hours, the mixture was cooled to 0C and borane-tetrahydrofuran complex (1.0M solution in tetrahydrofuran; 40 ml) was addedover fifteen minutes. After the addition was complete, the cooling bath was removed and the mixture allowed to warm to room temperature and stirred for seventeen hours. The reaction mixture was cooled to 0C, quenched with 1.0M aqueous sodium hydroxide solution (30 ml), diluted with saturated aqueous ammonium chloride solution (50 ml) and extracted with diethyl ether (2 x 100 ml), the combined organic layer washed with brine then dried (Na2SC"4) and evaporated. The residue was triturated with hexane and filtered to afford (2-chloro-6-methoxypyridin-4-yl)methanol (2.0 g) as a white solid. LCMS: Rt 1.16 min, m/z 174/176 [M+H]+. 1H-NMR (400 MHz, CDC13) delta (ppm): 1.96 (t, 1 H) 3.94 (s, 3 H) 4.67 (d, J=3.67 Hz, 2 H) 6.65 (d, J=0.86 Hz, 1 H) 6.91 (s, 1 H)
  • 7
  • [ 67-56-1 ]
  • [ 5398-44-7 ]
  • [ 15855-06-8 ]
YieldReaction ConditionsOperation in experiment
2-(1 -Ethyl -propyl)-6-methoxy-isonicotinic acid; a) To a solution of 2,6-dichloroisonicotinic acid (200 g, 1.04 mol) in methanol (3 L), 32% aq. NaOH (770 mL) is added. The stirred mixture becomes warm (34C) and is then heated to 700C for 4 h before it is cooled to rt. The mixture is neutralised by adding 32% aq. HCI (100 mL) and 25% aq. HCI (700 mL). The mixture is stirred at rt overnight. The white precipitate that forms is collected, washed with methanol and dried. The filtrate is evaporated and the residue is suspended in water (200 mL). The resulting mixture is heated to 600C. Solid material is collected, washed with water and dried. The combined crops give 2-chloro-6- methoxy-isonicotinic acid (183 g) as a white solid; LC-MS: tR = 0.80 min, [M+1]+ = 187.93.
a) To a solution of 2,6-dichloroisonicotinic acid (200 g, 1.04 mol) in methanol (3 L), 32% aq. NaOH (770 mL) is added. The stirred mixture becomes warm (34 C.) and is then heated to 70 C. for 4 h before it is cooled to rt. The mixture is neutralised by adding 32% aq. HCl (100 mL) and 25% aq. HCl (700 mL). The mixture is stirred at rt overnight. The white precipitate that forms is collected, washed with methanol and dried. The filtrate is evaporated and the residue is suspended in water (200 mL). The resulting mixture is heated to 60 C. Solid material is collected, washed with water and dried. The combined crops give 2-chloro-6-methoxy-isonicotinic acid (183 g) as a white solid; LC-MS: tR=0.80 min, [M+1]+=187.93.
183 g With sodium hydroxide; In water; at 70℃; for 4h; a) To a solution of 2,6-dichloroisonicotinic acid (200 g, 1.04 mol) in methanol (3 L), 32% aq. NaOH (770 mL) is added. The stirred mixture becomes warm (34 C.) and is then heated to 70 C. for 4 h before it is cooled to rt. The mixture is neutralised by adding 32% aq. HCl (100 mL) and 25% aq. HCl (700 mL). The mixture is stirred at rt overnight. The white precipitate that forms is collected, washed with methanol and dried. The filtrate is evaporated and the residue is suspended in water (200 mL). The resulting mixture is heated to 60 C. Solid material is collected, washed with water and dried. The combined crops give 2-chloro-6-methoxy-isonicotinic acid (183 g) as a white solid; LC-MS: tR=0.80 min, [M+1]+=187.93.
  • 8
  • [ 15855-06-8 ]
  • [ 74-88-4 ]
  • [ 42521-10-8 ]
YieldReaction ConditionsOperation in experiment
87% With potassium carbonate; In N,N-dimethyl-formamide; Example 16.1; 2-Chloro-6-methoxy-isonicotinic acid methyl ester; To <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (16 g, 85.3 mmol) in DMF (220 mL) were added K2CO3 (47 g, 341 mmol) and Mel (6.37 mL, 102.3 mmol). After stirring overnight, the reaction mixture was filtered and then concentrated. The residue was dissolved in ethyl acetate, washed with water (3 times) and brine, dried over anhydrous Na2SO4, filtered and concentrated. Purification by flash column chromatography eluted with 10-30% ethyl acetate in hexanes gave the title product (15 g, 87%).1H NMR (300 MHz, CDCl3): delta 7.45 (s, 1H), 7.23 (s, 1H), 3.98 (s, 3H), 3.95 (s, 3H).
87% With potassium carbonate; In N,N-dimethyl-formamide; Example 12.1; 2-Chloro-6-methoxy-isonicotinic acid methyl ester; To <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (16 g, 85 mmol) in DMF (220 mL) were added K2CO3 (47 g, 341 mmol) and MeI (6.37 mL, 102 mmol). After stirring for overnight, the reaction mixture was filtered and then concentrated. The residue was dissolved in ethyl acetate, washed with water (3 times) and brine, dried over anhydrous Na2SO4, filtered and concentrated. Purification by flash column chromatography eluted with 10-30% ethyl acetate in hexanes gave the title product (15 g, 87%).1H NMR (300 MHz, CDCl3): delta (ppm) 7.45 (s, 1H), 7.23 (s, 1H), 3.98 (s, 3H), 3.95 (s, 3H).
87% With potassium carbonate; In N,N-dimethyl-formamide; Example 9.1; 2-Chloro-6-methoxy-isonicotinic acid methyl ester; To <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (16 g, 85.3 mmol) in DMF (220 mL) were added K2CO3 (47 g, 341.2 mmol) and MeI (6.37 mL, 102.3 mmol). After stirring for overnight, the reaction mixture was filtered and then concentrated. The residue was dissolved in ethyl acetate, washed with water (3 times) and brine, dried over anhydrous Na2SO4, filtered and concentrated. Purification by flash column chromatography eluted with 10-30% ethyl acetate in hexanes gave the title product (15 g, 87%).1H NMR (300 MHz, CDCl3): delta (ppm) 7.45 (s, 1H), 7.23 (s, 1H), 3.98 (s, 3H), 3.95 (s, 3H)
  • 9
  • [ 67-56-1 ]
  • [ 15855-06-8 ]
  • [ 42521-10-8 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; at 65℃; for 20h; a) To a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (2.00 g, 10.7 mmol) in MeOH (100 mL), H2SO4 (2 mL) is added. The mixture is stirred at 65C for 20 h. The solution is cooled to rt. A precipitate forms. The solid material is collected, washed with MeOH and dried to give <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> methyl ester (1.66 g) as a white solid; LC- MS: tR = 1.29 min; [M+1]+ = 202.00.
With sulfuric acid; at 65℃; for 20h; To a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (2.00 g, 10.7 mmol) in methanol (100 mL), H2SO4 (2 mL) is added. The mixture is stirred at 65C for 20 h. The solution is cooled to rt. A precipitate forms. The solid material is collected, <n="49"/>washed with methanol and dried to give <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> methyl ester (1.66 g) as a white solid; LC-MS: tR = 1.29 min; [IVM]+ = 202.00.
With sulfuric acid; at 65℃; for 20h; To a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (2.00 g, 10.7 mmol) in MeOH (100 mL), H2SO4 (2 mL) is added. The mixture is stirred at 65 C. for 20 h. The solution is cooled to rt. A precipitate forms. The solid material is collected, washed with MeOH and dried to give <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> methyl ester (1.66 g) as a white solid; LC-MS: tR=1.29 min; [M+1]+=202.00.
sulfuric acid; for 24h;Reflux; b) To a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (244 g, 1.30 mol) in methanol (2.5 L), H2SO4 (20 mL) is added. The mixture is stirred at reflux for 24 h before it is cooled to 0C. The solid material is collected, washed with methanol (200 mL) and water (500 mL) and dried under HV to give <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> methyl ester (165 g) as a white solid; LC-MS: tR = 0.94 min, [M+1]+ = 201.89.
With sulfuric acid; at 65℃; for 20h; a) To a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (2.00 g, 10.7 mmol) in methanol (100 mL), H2SO4 (2 mL) is added. The mixture is stirred at 65 C. for 20 h. The solution is cooled to rt. A precipitate forms. The solid material is collected, washed with methanol and dried to give <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> methyl ester (1.66 g) as a white solid; LC-MS: tR=1.29 min; [M+1]+=202.00.
With sulfuric acid; at 0℃; for 24h;Reflux; b) To a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (244 g, 1.30 mol) in methanol (2.5 L), H2SO4 (20 mL) is added. The mixture is stirred at reflux for 24 h before it is cooled to 0 C. The solid material is collected, washed with methanol (200 mL) and water (500 mL) and dried under HV to give <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> methyl ester (165 g) as a white solid; LC-MS: tR=0.94 min, [M+1]+=201.89.
165 g With sulfuric acid; for 24h;Reflux; b) To a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (244 g, 1.30 mol) in methanol (2.5 L), H2SO4 (20 mL) is added. The mixture is stirred at reflux for 24 h before it is cooled to 0 C. The solid material is collected, washed with methanol (200 mL) and water (500 mL) and dried under HV to give <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> methyl ester (165 g) as a white solid; LC-MS: tR=0.94 min, [M+1]+=201.89.

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  • [ 15855-06-8 ]
  • [ 888729-53-1 ]
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  • [ 15855-06-8 ]
  • [ 888729-64-4 ]
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  • [ 15855-06-8 ]
  • [ 888729-54-2 ]
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; ;