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[ CAS No. 86604-78-6 ] {[proInfo.proName]}

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Chemical Structure| 86604-78-6
Chemical Structure| 86604-78-6
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Product Details of [ 86604-78-6 ]

CAS No. :86604-78-6 MDL No. :MFCD01076195
Formula : C9H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PSEPRWKZZJWRCB-UHFFFAOYSA-N
M.W : 167.21 Pubchem ID :737823
Synonyms :

Calculated chemistry of [ 86604-78-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.44
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.79
TPSA : 42.35 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) : -6.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.91
Log Po/w (XLOGP3) : 0.7
Log Po/w (WLOGP) : 1.05
Log Po/w (MLOGP) : 0.26
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 1.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.56
Solubility : 4.65 mg/ml ; 0.0278 mol/l
Class : Very soluble
Log S (Ali) : -1.17
Solubility : 11.4 mg/ml ; 0.0681 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.75
Solubility : 0.298 mg/ml ; 0.00178 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.87

Safety of [ 86604-78-6 ]

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 [ 86604-78-6 ]

* 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 [ 86604-78-6 ]
  • Downstream synthetic route of [ 86604-78-6 ]

[ 86604-78-6 ] Synthesis Path-Upstream   1~21

  • 1
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YieldReaction ConditionsOperation in experiment
83% With potassium iodide; sodium hydroxide In methanol; water for 4 h; Reflux Take 80 g of 2- (chloromethyl) -4-methoxy-3,5-dimethylpyridine hydrochloride,Add 300 mL of methanol,150 mL water,5.4 g Potassium iodide,40.4 g sodium hydroxide,Stirring heated to reflux, the reaction 4 h.Remove the methanol by rotary evaporation, add 300 mL of drinking water and extract with methylene chloride (150 mL × 3). Combine the organic phases. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated,50.0 g red oily liquid. Yield 83.0percent
Reference: [1] Patent: CN107382963, 2017, A, . Location in patent: Paragraph 0013; 0017; 0021
  • 2
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Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 6, p. 1049 - 1057
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 438 - 450
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1777 - 1788
[4] Patent: US4634710, 1987, A,
[5] Patent: US4766133, 1988, A,
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  • [ 150054-50-5 ]
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YieldReaction ConditionsOperation in experiment
55% With sodium methylate In <i>N</i>-methyl-acetamide; methanol; water EXAMPLE 8
Synthesis 2-hydroxymethyl-4-Methoxy-3,5-Lutidine
In a round bottom flask equipped with a stirrer, a condenser and a nitrogen bubbler, 4-Chloro-2-hydroxymethyl-3,5-Lutidine (1 eq.) was dissolved in Dimethylformamide (3-9 volumes) and Methanol (1.5-4.5 volumes).
Sodium methoxide (4 eq.) was added and the temperature was raised to (95-100.image. C.).
At the end of the reaction the solvent was distilled under vacuum.
Water (2 volumes) was added to the residue and the product was extracted with dichloromethane (2*4 volumes).
The combined organic extracts were dried over sodium sulfate, filtered and evaporated.
The crude product, 2-hydroxymethyl-4-Methoxy-3,5-lutidine, was obtained in 55percent yield.
In another work-up method, after evaporation of the dimethylformamide/methanol, water (2 volumes was added to the residue and the product was extracted with toluene (3*4 volumes).
The organic extracts were combined and while cooling and stirring HCl gas (1.2 eq.) was bubbled into solution.
The product 2-hydroxymethyl-4-Methoxy-3,5-lutidine hydrochloride salt was filtered and washed with toluene.
The crude product was obtained as a white solid in 50percent yield.
Reference: [1] Patent: US6437139, 2002, B1,
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Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1777 - 1788
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 6, p. 1049 - 1057
[3] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 438 - 450
[4] Patent: US5670526, 1997, A,
  • 5
  • [ 187222-18-0 ]
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Reference: [1] Heterocycles, 1997, vol. 45, # 1, p. 77 - 85
[2] Patent: US5616713, 1997, A,
  • 6
  • [ 84006-10-0 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 14, p. 1909 - 1912
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  • [ 130000-78-1 ]
  • [ 75-09-2 ]
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Reference: [1] Patent: US5066810, 1991, A,
  • 8
  • [ 91219-89-5 ]
  • [ 77-78-1 ]
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Reference: [1] Patent: US4544750, 1985, A,
  • 9
  • [ 86604-79-7 ]
  • [ 86604-78-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1777 - 1788
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 6, p. 1049 - 1057
  • 10
  • [ 74409-42-0 ]
  • [ 86604-78-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1777 - 1788
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 6, p. 1049 - 1057
  • 11
  • [ 50421-81-3 ]
  • [ 86604-78-6 ]
Reference: [1] Heterocycles, 1997, vol. 45, # 1, p. 77 - 85
[2] Heterocycles, 1997, vol. 45, # 1, p. 77 - 85
  • 12
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Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1777 - 1788
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Reference: [1] Heterocycles, 1997, vol. 45, # 1, p. 77 - 85
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Reference: [1] Heterocycles, 1997, vol. 45, # 1, p. 77 - 85
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Reference: [1] Heterocycles, 1997, vol. 45, # 1, p. 77 - 85
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Reference: [1] Heterocycles, 1997, vol. 45, # 1, p. 77 - 85
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  • [ 187222-16-8 ]
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Reference: [1] Heterocycles, 1997, vol. 45, # 1, p. 77 - 85
  • 18
  • [ 73590-58-6 ]
  • [ 37052-78-1 ]
  • [ 86604-78-6 ]
Reference: [1] Pharmazie, 2013, vol. 68, # 9, p. 749 - 754
  • 19
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  • [ 86604-75-3 ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride In dichloromethane at 20℃; for 1 h; To a solution [OF 4-METHOXY-3, 5-DIMETHYLPYRIDINEMETHANOL] (25.1 g, 0.15 mol) in dichloromethane (400 mL) was added a solution of thionyl chloride (18.8 g, 0. [158] mol) in dichloromethane (100 mL) over 30 min at room temperature under argon. After an additional 30 min of stirring at room temperature, the solvent was removed under reduced pressure. The solid residue was suspended in hexanes (200 mL) and filtered. The solid was washed with hexanes (50 mL) and air-dried to give 33.3 g (100percent) of the title compound as a white solid.
100% With thionyl chloride In dichloromethane at 20℃; for 1 h; To a solution of 4-methoxy-3,5-dimethylpyridinemethanol (25.1 g, 0.15 mol) in dichloromethane (400 mL) was added a solution of thionyl chloride (18.8 g, 0.158 mol) in dichloromethane (100 mL) over 30 min at room temperature under argon.
After an additional 30 min of stirring at room temperature, the solvent was removed under reduced pressure.
The solid residue was suspended in hexanes (200 mL) and filtered.
The solid was washed with hexanes (50 mL) and air-dried to give 33.3 g (100percent) of the title compound as a white solid.
98% With bis(trichloromethyl) carbonate; Triphenylphosphine oxide In toluene at 20 - 60℃; for 6 h; Ph3PO (43.78 g, 157.5 mmol) was dissolved in toluene (100 mL) in a 500 mL three-necked flask and BTC(14.84 g, 50 mmol) was dissolved in toluene (60 mL) and placed in a 150 mL constant pressure dropping funnel,BTC was added dropwise at room temperature,After the drop, the temperature is raised to 60 ° C.After incubation for 4 hours,2-hydroxymethyl-4-methoxy-3,5-dimethylpyridine (25.05 g, 150 mmol)Dissolved in toluene 75mL, at 40 ° C added to precipitate a white solid, incubation reaction 2 hours after stopping the reaction,The product was obtained by filtration to obtain a white solid which was dried to give 32.49 g of 2-chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride, the product yield was 98percent
86% With thionyl chloride In <i>N</i>-methyl-acetamide; dichloromethane; ethyl acetate EXAMPLE 3
2-CHLOROMETHYL-3,5-DIMETHYL-4-METHOXYPYRIDINE HYDROCHLORIDE
27.17 g (0.163 mole) of 2-hydroxymethyl-3,5-dimethyl-4methoxypyridine were dissolved in 48 ml of methylene chloride, 1.7 ml of dimethylformamide were added and thereafter 17.3 ml (0.238 mole) of thionyl chloride were added over 25 minutes, while holding the temperature to 25°-28° C.
Stirring was continued for a further 15 minutes at 20°-25° C. and the CH2 Cl2 was removed by distillation until a thick paste was formed.
96 ml of ethyl acetate were added, the temperature was allowed to reach room temperature and stirring was continued for 15 minutes.
The mixture was filtered and washed with ethyl acetate, to give 31.06 g of a white solid.
Yield 86percent.

Reference: [1] Patent: WO2004/9583, 2004, A2, . Location in patent: Page 156
[2] Patent: US2005/38076, 2005, A1, . Location in patent: Page/Page column 6
[3] Patent: CN107011252, 2017, A, . Location in patent: Paragraph 0063; 0064; 0066; 0068; 0072; 0074
[4] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1777 - 1788
[5] Patent: US5292886, 1994, A,
[6] Journal of Medicinal Chemistry, 1992, vol. 35, # 6, p. 1049 - 1057
[7] Patent: US4634710, 1987, A,
[8] Patent: US4766133, 1988, A,
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Reference: [1] Patent: US5670526, 1997, A,
  • 21
  • [ 37052-78-1 ]
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  • [ 73590-85-9 ]
Reference: [1] Patent: WO2004/35565, 2004, A1, . Location in patent: Page 5; 8-9
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