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[ CAS No. 106726-82-3 ] {[proInfo.proName]}

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Chemical Structure| 106726-82-3
Chemical Structure| 106726-82-3
Structure of 106726-82-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 106726-82-3 ]

CAS No. :106726-82-3 MDL No. :MFCD07367902
Formula : C8H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RLUVYUFWNPLVPL-UHFFFAOYSA-N
M.W : 162.15 Pubchem ID :13623673
Synonyms :

Calculated chemistry of [ 106726-82-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.23
TPSA : 62.98 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 0.42
Log Po/w (WLOGP) : 0.74
Log Po/w (MLOGP) : -0.28
Log Po/w (SILICOS-IT) : 1.17
Consensus Log Po/w : 0.71

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.35
Solubility : 7.28 mg/ml ; 0.0449 mol/l
Class : Very soluble
Log S (Ali) : -1.31
Solubility : 7.95 mg/ml ; 0.049 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.18
Solubility : 1.08 mg/ml ; 0.00665 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 106726-82-3 ]

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 [ 106726-82-3 ]

* 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 [ 106726-82-3 ]
  • Downstream synthetic route of [ 106726-82-3 ]

[ 106726-82-3 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 29681-44-5 ]
  • [ 106726-82-3 ]
YieldReaction ConditionsOperation in experiment
60% at 160℃; for 12 h; Inert atmosphere CuCN (5.22 g, 58.3 mmol) was added to a solution of methyl 5-bromonicotinate (6 g, 27.8 mmol) in dry DMF (150 mL).
The solution was purged with argon and heated to 160 °C for 12 h under argon atmosphere.
The reaction mixture was cooled to room temperature and then quenched with saturated NH4Cl solution.
Further EtOAc was added and the reaction mixture was stirred for 10 min.
The reaction mixture was filtered through a Celite plug, the organic layer was separated, washed with water and brine, and dried over anhydrous Na2SO4.
Solvent was evaporated under reduced pressure to get methyl-5-cyano-nicotinate as greenish-white solid (2.7g, yield 60percent): 1H NMR (300 MHz, DMSO-d6) δ 9.29-9.27 (m, 2H), 8.77 (s, 1H), 3.91 (s, 3H)
Reference: [1] Patent: EP2533783, 2015, B1, . Location in patent: Paragraph 0149-0150
  • 2
  • [ 557-21-1 ]
  • [ 106726-82-3 ]
Reference: [1] Synthetic Communications, 2007, vol. 37, # 3, p. 431 - 438
  • 3
  • [ 152803-05-9 ]
  • [ 106726-82-3 ]
Reference: [1] Patent: US5508293, 1996, A,
  • 4
  • [ 29681-44-5 ]
  • [ 544-92-3 ]
  • [ 106726-82-3 ]
YieldReaction ConditionsOperation in experiment
30.9% for 15 h; Heating / reflux Preparation 66 ;5-Cyano-nicotinic acid methyl ester; Reflux a solution of methyl 5-bromonicotinate (2.16 g, 10.0 mmol, 1 equiv) and copper (I) cyanide (1.79 g, 20.0 mmol, 2.0 equiv) in anhydr DMF (10 mL) for 15 h. After allowing to cool, filter the reaction mixture through Celite rinse with EtOAc (100 mL). A black precipitate forms in the filtrate. Wash the filtrate with salted H20 (3 x 100 mL). Dry the organic layer (anhydr Na2S04) and rotary evaporate (40 °C) giving 546 mg (33.7percent) of product as a light-yellow solid. Transfer this material to a column of silica gel (80 mm x 20 mm dia. ) and elute (20-35percent EtOAc/hex) to yield 501 mg (30.9percent) of 5- cyano-nicotinic acid methyl ester as an off-white solid. MS (m/e): 163.07 (M+1).
Reference: [1] Patent: WO2005/66126, 2005, A1, . Location in patent: Page/Page column 66
  • 5
  • [ 20826-04-4 ]
  • [ 106726-82-3 ]
Reference: [1] Patent: EP2533783, 2015, B1,
  • 6
  • [ 106726-82-3 ]
  • [ 135124-71-9 ]
YieldReaction ConditionsOperation in experiment
11%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 1.05 h;
Stage #2: With sodium hydroxide; water In tetrahydrofuran
Preparation 67; 5-Hydroxymethyl-nicotinonitrile; Add lithium aluminum hydride (l. OM in THF ; 1. 5mL, 1. 5mmol, 0. 5equiv) over a period of 3min to a solution of 5-cyano-nicotinic acid methyl ester (479mg, 2. 95mmol, lequiv) in anhydr THF (15mL) and cool to-78°C. After lh while still at-78°C, quench the reaction with H20 (60, uL), 5M aq NaOH (60pL), and more H20 (180μL). Filter the reaction mixture through paper. Rotary evaporate the filtrate (40°C) to give 369mg of material as a yellow solid. Transfer this material to a column of silica gel (130mm x 25mmdia. ) and elute (2percent MeOH/CH2Cl2) to yield 180mg of a mixture of ester, hemiacetal, and aldehyde as a yellow solid and 45mg (11percent) of 5-hydroxymethyl- nicotinonitrile as a yellow solid. MS (m/e) : 163.07 (M+1).
Reference: [1] Patent: WO2005/66126, 2005, A1, . Location in patent: Page/Page column 66-67
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