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[ CAS No. 1013648-04-8 ] {[proInfo.proName]}

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Chemical Structure| 1013648-04-8
Chemical Structure| 1013648-04-8
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Product Details of [ 1013648-04-8 ]

CAS No. :1013648-04-8 MDL No. :MFCD15144593
Formula : C8H7Cl2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QOTFUYQFPHLJTM-UHFFFAOYSA-N
M.W : 220.05 Pubchem ID :46911843
Synonyms :

Calculated chemistry of [ 1013648-04-8 ]

Physicochemical Properties

Num. heavy atoms : 13
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 : 50.5
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) : -5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.35
Log Po/w (XLOGP3) : 2.99
Log Po/w (WLOGP) : 2.48
Log Po/w (MLOGP) : 1.82
Log Po/w (SILICOS-IT) : 2.95
Consensus Log Po/w : 2.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.3
Solubility : 0.111 mg/ml ; 0.000504 mol/l
Class : Soluble
Log S (Ali) : -3.48
Solubility : 0.0734 mg/ml ; 0.000333 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.73
Solubility : 0.0412 mg/ml ; 0.000187 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 1013648-04-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1013648-04-8 ]

* 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.

  • Upstream synthesis route of [ 1013648-04-8 ]
  • Downstream synthetic route of [ 1013648-04-8 ]

[ 1013648-04-8 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 62774-90-7 ]
  • [ 74-88-4 ]
  • [ 1013648-04-8 ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6 h; A)
2,6-Dichloro-4-methyl-nicotinic acid methyl ester
To a solution of 8.05 g (39.1 mmol) of 2,6-dichloro-4-methyl-nicotinic acid [Lamm, G. Ger. Offen. (1977), DE 2538950] in 100 ml of DMF was added 8.10 g (58.6 mmol) of potassium carbonate.
While stirring, 12.16 ml=27.7 g (195.4 mmol) of iodomethane was added drop by drop and the reaction mixture was stirred for 6 hours at RT.
It was then poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated to give 8.47 g (99percent) of the title compound as light yellow solid. MS: 219.0 (M+, 2Cl).
99% With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere A) 2,6-Dichloro-4-methyl-nicotinic acid methyl ester; To a solution of 8.05 g (39.1 mmol) of 2,6-dichloro-4-methyl-nicotinic acid [Lamm, G. Ger. Offen. (1977), DE 2538950] in 100 ml of DMF was added 8.10 g (58.6 mmol) of potassium carbonate. While stirring, 12.16 ml=27.7 g (195.4 mmol) of iodomethane was added drop by drop and the reaction mixture was stirred for 6 hours at RT. It was then poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated to give 8.47 g (99percent) of the title compound as light yellow solid. MS: 219.0 (M+, 2Cl).
98% With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 3 h; a)
Synthesis of 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid methylester
To a solution of 5.0 g (24.3 mmol) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid in DMF (73 ml) were added 5.0 g (36.4 mmol) K2CO3 and 7.6 ml (121.3 mmol) iodomethane at 0° C.
The reaction mixture was stirred at RT for 3 h and was subsequently poured into water.
This mixture was extracted with EtOAc and the organic layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo.
Purification of the residue by CC (hexane/EtOAc 19:1) provided 5.2 g (23.7 mmol, 98percent) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid methylester.
98% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3 h; a) Synthesis of 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid methylester To a solution of 5.0 g (24.3 mmol) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid in DMF (73 ml) were added 5.0 g (36.4 mmol) K2C03 and 7.6 ml (121.3 mmol) iodomethane at 0 °C. The reaction mixture was stirred at RT for 3 h and was subsequently poured into water. This mixture was extracted with EtOAc and the organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 19:1 ) provided 5.2 g (23.7 mmol, 98percent) 2,6-dichloro-4-methyl-pyridine-3- carboxylic acid methylester.

Reference: [1] Patent: US2009/48238, 2009, A1, . Location in patent: Page/Page column 22
[2] Patent: US2009/318467, 2009, A1, . Location in patent: Page/Page column 23
[3] Patent: US2012/101079, 2012, A1, . Location in patent: Page/Page column 74
[4] Patent: WO2012/52167, 2012, A1, . Location in patent: Page/Page column 171-172
[5] Patent: US2017/183342, 2017, A1, . Location in patent: Paragraph 0231
  • 2
  • [ 56950-89-1 ]
  • [ 1013648-04-8 ]
Reference: [1] Patent: US2010/298221, 2010, A1,
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