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[ CAS No. 62774-90-7 ] {[proInfo.proName]}

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Chemical Structure| 62774-90-7
Chemical Structure| 62774-90-7
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Product Details of [ 62774-90-7 ]

CAS No. :62774-90-7 MDL No. :MFCD02932724
Formula : C7H5Cl2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QOSNTWMXACGOMD-UHFFFAOYSA-N
M.W : 206.03 Pubchem ID :676121
Synonyms :

Calculated chemistry of [ 62774-90-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.18
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) : -5.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 2.67
Log Po/w (WLOGP) : 2.4
Log Po/w (MLOGP) : 0.41
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 1.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.1
Solubility : 0.162 mg/ml ; 0.000788 mol/l
Class : Soluble
Log S (Ali) : -3.38
Solubility : 0.0867 mg/ml ; 0.000421 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.02
Solubility : 0.195 mg/ml ; 0.000946 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 62774-90-7 ]

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 [ 62774-90-7 ]

* 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 [ 62774-90-7 ]
  • Downstream synthetic route of [ 62774-90-7 ]

[ 62774-90-7 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 62774-90-7 ]
  • [ 75-03-6 ]
  • [ 108130-10-5 ]
YieldReaction ConditionsOperation in experiment
112 g
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 23℃; for 30 h;
Stage #2: at 23℃; for 18 h;
A mixture of 2,6-dichlor-4-methylpyridin-3-carboxylic acid (100 g, 485 mmol) and potassium carbonate (100 g, 728 mmol) in dimethylformamide (1.25 I) is stirred for 30 h at RT before ethyl iodide (59.5 ml, 728 mmol) is added and stirring is continued for 18 h. After completion of the reaction, water is added and the mixture is extracted with ethyl acetate (3x). The combined organic layers are washed with water (2x) and brine (1x), dried over magnesium sulphate and evaporated to dryness to yield 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid ethyl ester (112 g), which was used without further purification.
Reference: [1] Patent: WO2013/156154, 2013, A1, . Location in patent: Page/Page column 49
  • 2
  • [ 875-35-4 ]
  • [ 62774-90-7 ]
YieldReaction ConditionsOperation in experiment
96% at 70 - 105℃; for 2 h; Method 2
Concentrated nitric acid (14 mL) was added to cooled (0° C.) concentrated sulfuric acid (43 mL) maintaining the internal temperature below 10° C.
After addition, the acid mixture was heated to 70° C. and commercially available (Avocado) 2,6-dichloro-4-methylnicotinonitrile (20.0 g, 107 mmol) was added.
The temperature was raised until the internal temperature of the reaction reached 105° C.
At this point the heating was stopped and after 2 h, TLC analysis revealed that the reaction was complete.
The reaction mixture was cooled to room temperature, and slowly added to ice (100 g) with strong agitation.
The solid was filtered and washed with cold water (10 mL).
The solid was dissolved in EtOAc (100 mL) and the solution was dried over Na2SO4 and concentrated to give 2,6-dichloro-4-methyl-nicotinic acid (21.0 g, 96percent) as a white solid: Rf=0.20 (1:1 EtOAc:Hex).
Reference: [1] Patent: US6677352, 2004, B1, . Location in patent: Page/Page column 46
[2] Chemistry of Heterocyclic Compounds, 2004, vol. 40, # 3, p. 308 - 314
[3] Journal of Organic Chemistry, 2000, vol. 65, # 10, p. 3111 - 3115
[4] Patent: WO2016/33009, 2016, A1, . Location in patent: Page/Page column 17
  • 3
  • [ 38841-54-2 ]
  • [ 62774-90-7 ]
YieldReaction ConditionsOperation in experiment
97% at 20 - 60℃; for 7.25 h; [00230] A solution of sodium nitrite (2.73 g, 39.6 mmol) in water (15 mL) was added slowly to a solution of commercially available (Maybridge) 2,6-dichloro-4-methyl-nicotinamide (4.5 g, 22 mmol) in concentrated sulfuric acid resulting in evolution of heat and brown gas. The mixture was stirred at room temperature for 15 min, and then heated to 60° C. for 7 h. The solution was cooled to 0° C. and then water (15 mL) was added. The resulting white precipitate was collected by filtration and washed with hexane. The aqueous filtrate was extracted with EtOAc (3.x.) and the combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was combined with the white precipitate to afford 2,6-dichloro-4-methyl-nicotinic acid (4.39 g, 97percent) as a white solid: LCMS RT: 1.20 min, MH+: 206.3.
Reference: [1] Patent: US6677352, 2004, B1, . Location in patent: Page/Page column 46
[2] Chemistry of Heterocyclic Compounds, 2004, vol. 40, # 3, p. 308 - 314
[3] Patent: US2003/232818, 2003, A1, . Location in patent: Page 48
  • 4
  • [ 91591-70-7 ]
  • [ 62774-90-7 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 10, p. 3111 - 3115
  • 5
  • [ 5444-02-0 ]
  • [ 62774-90-7 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2004, vol. 40, # 3, p. 308 - 314
  • 6
  • [ 91591-70-7 ]
  • [ 62774-90-7 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 35, p. 6909 - 6913
  • 7
  • [ 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
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