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[ CAS No. 75358-90-6 ] {[proInfo.proName]}

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Chemical Structure| 75358-90-6
Chemical Structure| 75358-90-6
Structure of 75358-90-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 75358-90-6 ]

CAS No. :75358-90-6 MDL No. :MFCD07368152
Formula : C9H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :KOAWFXMHARNHJY-UHFFFAOYSA-N
M.W : 176.17 Pubchem ID :12747366
Synonyms :

Calculated chemistry of [ 75358-90-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.04
TPSA : 62.98 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) : -6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 1.12
Log Po/w (WLOGP) : 1.13
Log Po/w (MLOGP) : 0.04
Log Po/w (SILICOS-IT) : 1.51
Consensus Log Po/w : 1.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.78
Solubility : 2.91 mg/ml ; 0.0165 mol/l
Class : Very soluble
Log S (Ali) : -2.04
Solubility : 1.62 mg/ml ; 0.0092 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.59
Solubility : 0.454 mg/ml ; 0.00258 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.99

Safety of [ 75358-90-6 ]

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 [ 75358-90-6 ]

* 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 [ 75358-90-6 ]
  • Downstream synthetic route of [ 75358-90-6 ]

[ 75358-90-6 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 14906-63-9 ]
  • [ 7677-24-9 ]
  • [ 76196-79-7 ]
  • [ 75358-90-6 ]
YieldReaction ConditionsOperation in experiment
5.7 g
Stage #1: With N,N-Dimethylcarbamoyl chloride In dichloromethane at 20℃; for 48 h; Inert atmosphere
Stage #2: With potassium carbonate In water
[0141] To a solution of 3-ethoxycarbonylpyridine N-oxide in 330 mL of DCM were added trimethylsilyl cyanide (TMSCN) (1 1.0 g, 65.9 mmol, 1.0 eq) and dimethylcarbamoyl chloride (7.1 g, 65.9 mmol, 1.0 eq) and the reaction mixture was stirred at rt for 2 days. Then 10percent K2C03 was slowly added to make the reaction mixture basic.Organic layer was separated, dried and evaporated to provide the crude, which was purified by column chromatography to provide compounds A (5.7 g) and B (3.5 g).
5.7 g With potassium carbonate; N,N-Dimethylcarbamoyl chloride In dichloromethane at 20℃; for 48 h; [0248] To a solution of 3-ethoxycarbonylpyridine N-oxide in 330 mL of DCM were added trimethylsilyl cyanide (TMSCN) (11.0 g, 65.9 mmol, 1.0 eq) and dimethylcarbamoyl chloride(7.1 g, 65.9 mmol, 1.0 eq) and the reaction mixture was stirred at rt for 2 days. Then 10percent K2C03 was slowly added to make the reaction mixture basic. Organic layer was separated, dried and evaporated to provide the crude, which was purified by column chromatography to provide compounds A (5.7 g) and B (3.5 g).
5.7 g With N,N-Dimethylcarbamoyl chloride In dichloromethane at 20℃; for 48 h; To a solution of 3-ethoxycarbonylpyridine N-oxide in 330 mE of DCM were added trimethylsilyl cyanide (TMSCN) (11.0 g, 65.9 mmol, 1.0 eq) and dimethylcarbamoyl chloride (7.1 g, 65.9 mmol, 1.0 eq) and the reaction mixture was stirred at it for 2 days. Then 10percent K2C03 was slowly added to make the reaction mixture basic. Organic layer was separated, dried and evaporated to provide the crude, which was purified by column chromatography to provide compounds A (5.7 g) and B (3.5 g).
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 2, p. 565 - 571
[2] Patent: WO2013/102142, 2013, A1, . Location in patent: Paragraph 0141
[3] Patent: WO2013/102145, 2013, A1, . Location in patent: Paragraph 0247
[4] Patent: US2015/344483, 2015, A1, . Location in patent: Paragraph 0474; 0475
  • 2
  • [ 614-18-6 ]
  • [ 76196-79-7 ]
  • [ 75358-90-6 ]
Reference: [1] Patent: WO2013/102145, 2013, A1,
[2] Patent: US2015/344483, 2015, A1,
  • 3
  • [ 557-21-1 ]
  • [ 1452-94-4 ]
  • [ 75358-90-6 ]
YieldReaction ConditionsOperation in experiment
100% With 1,1'-bis-(diphenylphosphino)ferrocene; zinc In ISOPROPYLAMIDE at 120℃; for 1 h; To ethyl 2-chloronicotinate (15.0 g, 81 mmol) in anhydrous N, N-dimethylacetamide (75 ml) was added zinc cyanide (5.71 g, 48.6 mmol), Pd2 (dba) 3 (742 mg, 0.81 mmol), zinc (636 mg, 9.72 mmol), and 1, 1APOS;BIS (diphenylphosphino) ferrocene (898 mg, 1.62 mmol), and the resulting mixture heated at 120 °C for 1 hour. The mixture was cooled to room temperature and partitioned between water (300 ml) and diethyl ether (150 ml), the mixture was filtered through Celiez and the phases separated. The aqueous phase was further extracted with diethyl ether (2 x 100 ml), the combined diethyl ether layers washed with saturated NACI, dried over NA2SO4, FILTERED and evaporated to give the title compound (14.26 g, 100percent).
Reference: [1] Patent: WO2004/46133, 2004, A1, . Location in patent: Page 31
  • 4
  • [ 14906-63-9 ]
  • [ 7677-24-9 ]
  • [ 76196-79-7 ]
  • [ 75358-90-6 ]
YieldReaction ConditionsOperation in experiment
5.7 g
Stage #1: With N,N-Dimethylcarbamoyl chloride In dichloromethane at 20℃; for 48 h; Inert atmosphere
Stage #2: With potassium carbonate In water
[0141] To a solution of 3-ethoxycarbonylpyridine N-oxide in 330 mL of DCM were added trimethylsilyl cyanide (TMSCN) (1 1.0 g, 65.9 mmol, 1.0 eq) and dimethylcarbamoyl chloride (7.1 g, 65.9 mmol, 1.0 eq) and the reaction mixture was stirred at rt for 2 days. Then 10percent K2C03 was slowly added to make the reaction mixture basic.Organic layer was separated, dried and evaporated to provide the crude, which was purified by column chromatography to provide compounds A (5.7 g) and B (3.5 g).
5.7 g With potassium carbonate; N,N-Dimethylcarbamoyl chloride In dichloromethane at 20℃; for 48 h; [0248] To a solution of 3-ethoxycarbonylpyridine N-oxide in 330 mL of DCM were added trimethylsilyl cyanide (TMSCN) (11.0 g, 65.9 mmol, 1.0 eq) and dimethylcarbamoyl chloride(7.1 g, 65.9 mmol, 1.0 eq) and the reaction mixture was stirred at rt for 2 days. Then 10percent K2C03 was slowly added to make the reaction mixture basic. Organic layer was separated, dried and evaporated to provide the crude, which was purified by column chromatography to provide compounds A (5.7 g) and B (3.5 g).
5.7 g With N,N-Dimethylcarbamoyl chloride In dichloromethane at 20℃; for 48 h; To a solution of 3-ethoxycarbonylpyridine N-oxide in 330 mE of DCM were added trimethylsilyl cyanide (TMSCN) (11.0 g, 65.9 mmol, 1.0 eq) and dimethylcarbamoyl chloride (7.1 g, 65.9 mmol, 1.0 eq) and the reaction mixture was stirred at it for 2 days. Then 10percent K2C03 was slowly added to make the reaction mixture basic. Organic layer was separated, dried and evaporated to provide the crude, which was purified by column chromatography to provide compounds A (5.7 g) and B (3.5 g).
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 2, p. 565 - 571
[2] Patent: WO2013/102142, 2013, A1, . Location in patent: Paragraph 0141
[3] Patent: WO2013/102145, 2013, A1, . Location in patent: Paragraph 0247
[4] Patent: US2015/344483, 2015, A1, . Location in patent: Paragraph 0474; 0475
  • 5
  • [ 5860-70-8 ]
  • [ 541-41-3 ]
  • [ 75358-90-6 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1980, vol. 89, # 3, p. 205 - 232
  • 6
  • [ 614-18-6 ]
  • [ 76196-79-7 ]
  • [ 75358-90-6 ]
Reference: [1] Patent: WO2013/102145, 2013, A1,
[2] Patent: US2015/344483, 2015, A1,
  • 7
  • [ 614-18-6 ]
  • [ 75358-90-6 ]
Reference: [1] Patent: WO2013/102142, 2013, A1,
  • 8
  • [ 75358-90-6 ]
  • [ 697739-12-1 ]
Reference: [1] Patent: US2015/344483, 2015, A1,
[2] Patent: WO2013/102142, 2013, A1,
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