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[ CAS No. 60032-57-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 60032-57-7
Chemical Structure| 60032-57-7
Chemical Structure| 60032-57-7
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Product Details of [ 60032-57-7 ]

CAS No. :60032-57-7 MDL No. :MFCD08234911
Formula : C7H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :JHRPHASLIZOEBJ-UHFFFAOYSA-N
M.W : 121.14 Pubchem ID :11083881
Synonyms :

Calculated chemistry of [ 60032-57-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.59
TPSA : 29.96 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) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.27
Log Po/w (XLOGP3) : 0.71
Log Po/w (WLOGP) : 1.2
Log Po/w (MLOGP) : 0.13
Log Po/w (SILICOS-IT) : 1.96
Consensus Log Po/w : 1.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.47
Solubility : 4.15 mg/ml ; 0.0342 mol/l
Class : Very soluble
Log S (Ali) : -0.92
Solubility : 14.7 mg/ml ; 0.121 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.31
Solubility : 0.589 mg/ml ; 0.00486 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.03

Safety of [ 60032-57-7 ]

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 [ 60032-57-7 ]

* 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 [ 60032-57-7 ]
  • Downstream synthetic route of [ 60032-57-7 ]

[ 60032-57-7 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 56826-61-0 ]
  • [ 60032-57-7 ]
YieldReaction ConditionsOperation in experiment
85% With manganese(IV) oxide In dichloromethane for 48 h; Heating / reflux A mixture of the 3-hydroxymethyl-2-methylpyridine (9.Og, 73.1mmol) and manganese (IV) dioxide (28.1g, 322mmol) in DCM (100ml) was heated at reflux for two days. The insolubles were removed by filtration through diatomaceous earth and the filter pad was washed with methanol / DCM. The solvent was removed from the filtrate by evaporation to give 2-methylpyridine-3-carboxaldehyde (7.5g, 85percent) as an oil; NMR Spectrum 2.78 (s, 3H), 7.43 (dd, IH), 8.15 (dd, IH), 8.66 (dd, IH).
85% With manganese(IV) oxide In dichloromethane for 48 h; Heating / reflux A mixture of the 3-hydroxymethyl-2-methylpyridine (9.Og, 73.1mmol) and manganese (IV) dioxide (28. Ig, 322mmol) in DCM (100ml) was heated at reflux for two days. The insolubles were removed by filtration through diatomaceous earth and the filter pad was washed with methanol / DCM. The solvent was removed from the filtrate by evaporation to give 2-methylρyridine-3-carboxaldehyde (7.5g, 85percent) as an oil; NMR Spectrum 2.78 (s, 3H), 7.43 (dd, IH), 8.15 (dd, IH), 8.66 (dd, IH).
60% With manganese(IV) oxide In dichloromethaneReflux; Inert atmosphere N-((4-chloro-2-methylphenyl)(phenyl)methyl)-2-(2-((2-methylpyridin-3-yl)methyl)benzofuran-5- yl)acetamidea) 2-methylnicotinaldehydeTo a stirred solution of (2-methylpyridin-3-yl)methanol (200 mg, 1.6 mmol) in CH2CI2 (10 mL) was added M11O2 (200 mg, 2.3 mmol). The reaction mixture was refluxed overnight under N2. The solid was removed by filtration and the filtrate was concentrated. The resultant residue was purified by flash chromatography (50percent EtO Ac/petroleum ether) to afford the title compound (120 mg, 60percent) as a colorless liquid. LCMS-P1 : 122.0 [M+H]+; Rt: 0.344 min.
60% With manganese(IV) oxide In dichloromethaneInert atmosphere; Reflux (a) 2-methyinicotinaidehyde: To a stirred solution of (2-methyipyridin-3-yl)methanoi (200 mg, 1.6 mmol) in CH2CI2 (10 mL) was added Mn02 (200 mg, 2.3 mmol). The mixture wasrefluxed overnight under rutrogcn. The solid was removed by fihration. After removal ofsolvent, the crude product was purified by silica gel column chromotography (petroleumether/EtOAc = i/i) to give the title compound (120 rug, 60percent) as a colorless liquid .LCMS-PI:122.0 [M+H]t R = 0.344 miii.

Reference: [1] Patent: WO2006/106307, 2006, A1, . Location in patent: Page/Page column 91
[2] Patent: WO2006/100461, 2006, A1, . Location in patent: Page/Page column 83
[3] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 9, p. 1841 - 1849
[4] Patent: WO2013/19682, 2013, A1, . Location in patent: Page/Page column 101
[5] Patent: WO2013/19626, 2013, A1, . Location in patent: Page/Page column 27
[6] Journal of Medicinal Chemistry, 1989, vol. 32, # 3, p. 583 - 593
[7] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1315 - 1324
[8] Patent: US2008/85887, 2008, A1, . Location in patent: Page/Page column 21
[9] Patent: US2005/131017, 2005, A1, . Location in patent: Page/Page column 105
[10] Patent: WO2013/19621, 2013, A1, . Location in patent: Page/Page column 73; 74
[11] Advanced Synthesis and Catalysis, 2017, vol. 359, # 13, p. 2191 - 2195
[12] Organic and Biomolecular Chemistry, 2017, vol. 15, # 31, p. 6474 - 6477
  • 2
  • [ 68-12-2 ]
  • [ 38749-79-0 ]
  • [ 60032-57-7 ]
YieldReaction ConditionsOperation in experiment
31%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at -78℃; for 1 h;
To a solution of 3-bromo-2-methylpyridine (148; 10 g, 58.1 mmol) in THF (150 mL) was added n-BuLi (2.5 M, 25.6 mL) at -78 °C. The reaction mixture was stirred at this temperature for Ih. DMF (1.30 mL) was then added and the resulting reaction mixture was stirred for 1 h at -78 0C. The reaction was quenched by the addition of aq. NH4Cl. Upon warming to room temperature, the mixture was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography to afford 2-methylnicotinaldehyde 149 (2.18 g, 31percent).
31%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at -78℃; for 1 h;
Example 21. Synthesis of 2-(2-methylpyridin-3-yl)-N-(thiazol-2-yl)-[l,2,4]triazolo[l,5- a]pyridine-8-carboxamide (Compound 239):Step 1) Preparation of 2-methylnicotinaldehyde (89): To a solution of 3-bromo-2-methylpyridine (88; 10 g, 58.1 mmol) in THF (150 mL) was added n-BuLi (2.5 M, 25.6 mL) at -78 0C. The reaction mixture was stirred at this temperature for Ih. DMF (1.30 mL) was then added and the resulting reaction mixture was stirred for 1 h at -78 0C. The reaction was quenched by the addition of aq. NH4Cl. Upon warming to room temperature, the mixture was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography to afford 2-methylnicotinaldehyde 89 (2.18 g, 31percent).
Reference: [1] Patent: WO2010/3048, 2010, A1, . Location in patent: Page/Page column 129
[2] Patent: WO2009/146358, 2009, A1, . Location in patent: Page/Page column 95
  • 3
  • [ 469864-28-6 ]
  • [ 60032-57-7 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2009, vol. 45, # 9, p. 1053 - 1057
  • 4
  • [ 1721-26-2 ]
  • [ 60032-57-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 9, p. 1841 - 1849
[2] Journal of Medicinal Chemistry, 1989, vol. 32, # 3, p. 583 - 593
[3] Chemische Berichte, 1949, vol. 82, p. 216
[4] Advanced Synthesis and Catalysis, 2017, vol. 359, # 13, p. 2191 - 2195
[5] Organic and Biomolecular Chemistry, 2017, vol. 15, # 31, p. 6474 - 6477
  • 5
  • [ 312933-33-8 ]
  • [ 60032-57-7 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1980, # 3, p. 92 - 93
  • 6
  • [ 312933-33-8 ]
  • [ 60032-57-7 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1980, # 3, p. 92 - 93
[2] Journal of the Chemical Society, Chemical Communications, 1980, # 3, p. 92 - 93
  • 7
  • [ 90643-19-9 ]
  • [ 60032-57-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 9, p. 1841 - 1849
  • 8
  • [ 65719-09-7 ]
  • [ 60032-57-7 ]
Reference: [1] Patent: WO2013/19621, 2013, A1,
  • 9
  • [ 380635-35-8 ]
  • [ 60032-57-7 ]
Reference: [1] Chemische Berichte, 1949, vol. 82, p. 216
  • 10
  • [ 197079-01-9 ]
  • [ 60032-57-7 ]
Reference: [1] Chemische Berichte, 1949, vol. 82, p. 216
  • 11
  • [ 60032-57-7 ]
  • [ 64987-16-2 ]
  • [ 56826-61-0 ]
  • [ 1421928-97-3 ]
Reference: [1] Patent: WO2013/19621, 2013, A1, . Location in patent: Page/Page column 74
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