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[ CAS No. 206201-64-1 ] {[proInfo.proName]}

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Chemical Structure| 206201-64-1
Chemical Structure| 206201-64-1
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Product Details of [ 206201-64-1 ]

CAS No. :206201-64-1 MDL No. :MFCD13189079
Formula : C7H4N2O Boiling Point : -
Linear Structure Formula :- InChI Key :DMDMMMFMXWZSLM-UHFFFAOYSA-N
M.W : 132.12 Pubchem ID :21364144
Synonyms :

Calculated chemistry of [ 206201-64-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.34
TPSA : 53.75 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) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.62
Log Po/w (XLOGP3) : 0.37
Log Po/w (WLOGP) : 0.77
Log Po/w (MLOGP) : -0.84
Log Po/w (SILICOS-IT) : 1.46
Consensus Log Po/w : 0.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.27
Solubility : 7.09 mg/ml ; 0.0537 mol/l
Class : Very soluble
Log S (Ali) : -1.06
Solubility : 11.4 mg/ml ; 0.0863 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.02
Solubility : 1.25 mg/ml ; 0.00946 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 206201-64-1 ]

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

Application In Synthesis of [ 206201-64-1 ]

* 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 [ 206201-64-1 ]
  • Downstream synthetic route of [ 206201-64-1 ]

[ 206201-64-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 3222-48-8 ]
  • [ 206201-64-1 ]
YieldReaction ConditionsOperation in experiment
50%
Stage #1: at 150℃; for 0.333333 h;
Stage #2: at 20℃;
Preparation 18 6-FormylnicotinonitrileA mixture of 6-methylnicotinonitrile (10.0 g, 84.6 mmol) and iodine (20.0 g, 78.8 mmol) in dimethylsulfoxide (150 mL) was heated at 15O0C under nitrogen for 20 minutes (reaction exhaust was scrubbed with bleach to remove dimethyl sulfide). After cooling to room temperature saturated aqueous sodium bicarbonate (200 mL) was added carefully and the resulting mixture was extracted with toluene (3 x 100 mL). The combined organic extracts were washed with brine, dried (MgSO4) and evaporated to give the desired product as an orange oil (5.65 g, 50percent) which was used without further purification. 1H NMR (CDCI3, 400 MHz) δ 8.06 (1H, d), 8.17 (1H, dd), 9.05 (1H, d), 10.12 (1H, s).
Reference: [1] Chemical Science, 2015, vol. 7, # 1, p. 346 - 357
[2] Patent: WO2007/96763, 2007, A2, . Location in patent: Page/Page column 60
[3] Patent: US2002/19527, 2002, A1,
[4] Patent: WO2013/6408, 2013, A1, . Location in patent: Page/Page column 43
[5] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 559 - 576
  • 2
  • [ 31795-61-6 ]
  • [ 206201-64-1 ]
YieldReaction ConditionsOperation in experiment
48%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.333333 h; Cooling with acetone-dry ice
Stage #2: at -78℃; for 2 h; Cooling with acetone-dry ice
Oxalyl chloride (936 mg, 7.38 mmol) is dissolved in dichlormethane (8 ml) under an argon atmosphere and cooled to-78 C in an acetone dry-ice bath. Dimethylsulfoxide (1. 153 g, 14. 76 mmol) is added dropwise and the mixture is stirred for 20 minutes at - 78 C. The compound of Example 32A (900 mg, 6.71 mmol) is added dropwise as a dichloromethane (7 ml) solution. The reaction is stirred for an additional two hours at - 78 C. Triethylamine (3.05 g, 30.19 mmol) is added and the reaction is kept at-78 C for 10 minutes, then allowed to warm to room temperature. The reaction is quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The ethyl acetate phase is washed with bicarbonate and brine, dried over magnesium <Desc/Clms Page number 48>sulphate monohydrate, filtered and concentrated to afford a yellow oil. The crude oil is purified by column chromatography on silica gel with dichloromethane as eluent. Yield: 424 mg (48percent of th.) HPLC (method 8): Rt1. 19 min MS(EI) :m/z= 132 (M) +IH-NMR (200 MHz,DMSO-d6) :6 = 5.69 (t, 1H); 7.65 (d, 1H); 8.31 (dd, 1H); 8.93 (d, 1H) ppm.
Reference: [1] Patent: WO2004/20412, 2004, A1, . Location in patent: Page 47; 48
  • 3
  • [ 1531599-37-7 ]
  • [ 206201-64-1 ]
YieldReaction ConditionsOperation in experiment
63% With sodium periodate In tetrahydrofuran; water for 2 h; To a stirred solution of the enamine (6.16g, 35.6mmol) in THF (130mL) was added a solution of sodium periodate (23.0g, 107mmol) in water (130mL). The mixture was stirred for 2h and filtered (Celite). The filtrate was diluted with water and extracted into CH2Cl2. Extracts were washed with brine, dried (MgSO4) and evaporated. The product was purified by flash chromatography on silica eluting with hexanes/ethyl acetate (7:3) to give the aldehyde (2.94g, 63percent): mp 91–92°C; 1H NMR δ 10.03 (d, J=0.7Hz, 1H), 9.28 (dd, J1=2.0Hz, J2=0.9Hz, 1H), 8.58 (ddd, J1=8.1Hz, J2=2.0Hz, J3=0.7Hz, 1H), 8.07 (dd, J1=8.1Hz, J2=0.9Hz, 1H). Anal. Calcd for C7H4N2O: C, 63.64; H, 3.05; N, 21.20. Found: C, 63.57; H, 3.00; N, 21.11.
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 559 - 576
  • 4
  • [ 16173-99-2 ]
  • [ 206201-64-1 ]
Reference: [1] Patent: WO2009/5646, 2009, A2, . Location in patent: Page/Page column 147
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