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[ CAS No. 669050-69-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 669050-69-5
Chemical Structure| 669050-69-5
Chemical Structure| 669050-69-5
Structure of 669050-69-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 669050-69-5 ]

CAS No. :669050-69-5 MDL No. :MFCD06738282
Formula : C8H6N2O Boiling Point : -
Linear Structure Formula :- InChI Key :JTWYTTXTJFDYAG-UHFFFAOYSA-N
M.W : 146.15 Pubchem ID :18538368
Synonyms :

Calculated chemistry of [ 669050-69-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.48
TPSA : 45.75 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) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.58
Log Po/w (XLOGP3) : 1.69
Log Po/w (WLOGP) : 1.38
Log Po/w (MLOGP) : 0.49
Log Po/w (SILICOS-IT) : 2.17
Consensus Log Po/w : 1.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.35
Solubility : 0.652 mg/ml ; 0.00446 mol/l
Class : Soluble
Log S (Ali) : -2.27
Solubility : 0.793 mg/ml ; 0.00542 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.84
Solubility : 0.213 mg/ml ; 0.00146 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.16

Safety of [ 669050-69-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 669050-69-5 ]

* 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 [ 669050-69-5 ]
  • Downstream synthetic route of [ 669050-69-5 ]

[ 669050-69-5 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 916902-55-1 ]
  • [ 669050-69-5 ]
YieldReaction ConditionsOperation in experiment
98% With manganese(IV) oxide In dichloromethane at 20℃; To a solution of the (lH-indazole-6-yl)methanol {Eur. J. Inorg. Chem. 2006, 5, 980 - 987) (278.0 mg, 1.876 mmol) in 10.0 ml of CH2Cl2 was added MnO2 (816.0 mg, 9.38 mmol) and the mixture was stirred at room temperature overnight. Filtered, washed with CH2C12 (2x25 ml). The filtrate was washed with water and brine, dried (MgSO4), filtered and the solvent <n="39"/>was evaporated under reduced pressure to give 270 mg of the crude title compound as a white solid (0.27 g, 98percent). MS (Electrospray): m/z 147.1 (M+H).
1.3 g With Dess-Martin periodane In tetrahydrofuran; dichloromethane at 20 - 25℃; for 16 h; To the stirred solution of 1H-indazol-6-ylmethanol (1.5g) in DCM (15 ml) and THF (15 ml) was added Dess Martin Periodinane (4.29 g) and stirred at room temperature for 16 h. DCM was added and filtered through celite. Filtrate was epaporated under vacuum to afford the title com- pound (1.3 g). HPLC/MS (method 1): Rt:1.290 min; m / z = 146 (M+1).
Reference: [1] Patent: WO2009/54983, 2009, A1, . Location in patent: Page/Page column 37-38
[2] Patent: US2008/200535, 2008, A1, . Location in patent: Page/Page column 133
[3] Patent: WO2005/44817, 2005, A1, . Location in patent: Page/Page column 101-102
[4] Patent: WO2018/177781, 2018, A1, . Location in patent: Page/Page column 82; 99-100
  • 2
  • [ 79762-54-2 ]
  • [ 68-12-2 ]
  • [ 669050-69-5 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; for 1 h;
Stage #2: With sec.-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.25 h;
Stage #3: at 20℃;
To a suspension of 60 percent NaH (10.0 g, 0.24 mol) in THF (240 mL) was added a suspension of 6-bromo-lH-indazole (39.4 g, 0.2 mol) in THF (280 mL) dropwise over 45 min. After addition, the resulting mixture was stirred for 1 h at rt to give a dark red clear solution which was cooled to -78 0C.5-BuLi (1.4 M in <n="86"/>hexane, 300 mL, 0.42 mol) was added dropwsie over 1 h. During this addition, additional THF (130 mL) was added to keep the mixture stirring. After the addition, the resulting mixture was stirred for 75 min at -78 0C; DMF (90 mL) was added dropwise (note: reaction solidified upon addition of DMF, occasional warming was needed to keep the mixture stirring). The resulting mixture was stirred at it overnight and cooled to 0 0C. Solid NH4Cl and saturated NH4Cl were added to quench the reaction and bring the pH to about 7. The product was extracted with EtOAc (800 mL + 200 mL +300 mL, 1.3 L in total) and the combined extracts were washed with H2O (300 mL x 3) and dried (Na2SO4). Evaporation of the solvent gave a dark red solid which was triturated by EtOAc (4 times, the last filtrate was purified by flash chromatography) to give the title compound (16.96 g in total, 58percent) as yellow brown solid. 1H NMR (400 MHz, DMSO-d6) δ 13.62 (s, IH, NH), 10.12 (s, IH, CHO), 8.23 (s, IH), 8.17 (s, IH), 7.93 (d, J = 8.4 Hz, IH), 7.59 (d, J = 8.4 Hz, IH); MS ESI 147.0 [M + H]+, calcd for [C8H6N2O+ H]+ 147.0.
Reference: [1] Patent: WO2009/79767, 2009, A1, . Location in patent: Page/Page column 84-85
  • 3
  • [ 170487-40-8 ]
  • [ 669050-69-5 ]
Reference: [1] Patent: WO2018/177781, 2018, A1,
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