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[ CAS No. 1082042-15-6 ] {[proInfo.proName]}

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Chemical Structure| 1082042-15-6
Chemical Structure| 1082042-15-6
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Product Details of [ 1082042-15-6 ]

CAS No. :1082042-15-6 MDL No. :MFCD11007971
Formula : C8H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :KJEVVDTWFHNFBO-UHFFFAOYSA-N
M.W : 148.16 Pubchem ID :135742461
Synonyms :

Calculated chemistry of [ 1082042-15-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 43.08
TPSA : 48.91 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) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.98
Log Po/w (XLOGP3) : 1.56
Log Po/w (WLOGP) : 1.58
Log Po/w (MLOGP) : 0.84
Log Po/w (SILICOS-IT) : 2.0
Consensus Log Po/w : 1.39

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 : 0.667 mg/ml ; 0.0045 mol/l
Class : Soluble
Log S (Ali) : -2.2
Solubility : 0.941 mg/ml ; 0.00635 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.7
Solubility : 0.294 mg/ml ; 0.00198 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.28

Safety of [ 1082042-15-6 ]

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 [ 1082042-15-6 ]

* 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.

  • Downstream synthetic route of [ 1082042-15-6 ]

[ 1082042-15-6 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 1041205-43-9 ]
  • [ 1082042-15-6 ]
  • [ 2803901-35-9 ]
YieldReaction ConditionsOperation in experiment
21% With tripotassium phosphate tribasic; copper (I) iodide; trans-N,N’-dimethylcyclohexane-1,2-diamine In 1,4-dioxane at 90℃; for 4h; Sealed tube; 68.1; 69.2 Step 2: 1-(1-(Difluoromethyl)-1H-pyrazol-4-yl)-5-methyl-1H-indazol-6-ol A mixture of 5-methyl-1H g, 1.69 mmol), 1-(difluoromethyl)- 4-iodopyrazole (494.02 mg, 2.02 mmol), (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (120.01 mg, 0.84 mmol), copper (I) iodide (64.27 mg, 0.340 mmol), and tripotassium phosphate (1073.16 mg, 5.06 mmol) in dry 1,4-dioxane (5.5 mL) was stirred at 90 °C for 4 hrs in a sealed vial. The reaction mixture was partitioned between H2O and EtOAc, the phases were separated, and the aqueous layer was extracted with EtOAc (2x). The combined organic phases were washed with brine (1x), dried over anhydrous Na2SO4 and evaporated to dryness. The material was purified by flash silica gel chromatography using a 0-40% EtOAc/cyclohexane gradient eluent to afford the title compound (95 mg, 21%) as a white solid. 'H NMR (400 MHz, DMSO-d6) δ 9.92 (1 H, br. s.) 8.69 (1 H, s) 8.21 (1 H, s) 8.07 (1 H, d, J=0.66 Hz) 7.72 - 8.05 (1 H, m) 7.52 (1 H, s) 7.00 (1 H, s) 2.22 (3 H, s). MS-ESI (m/z) calc’d for C12H11F2N4O [M+H]+: 265.1, Found 265.1.
21% With tripotassium phosphate tribasic; copper (I) iodide; trans-N,N’-dimethylcyclohexane-1,2-diamine In 1,4-dioxane at 90℃; for 4h; Sealed tube; 68.1; 69.2 Step 2: 1-(1-(Difluoromethyl)-1H-pyrazol-4-yl)-5-methyl-1H-indazol-6-ol A mixture of 5-methyl-1H g, 1.69 mmol), 1-(difluoromethyl)- 4-iodopyrazole (494.02 mg, 2.02 mmol), (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (120.01 mg, 0.84 mmol), copper (I) iodide (64.27 mg, 0.340 mmol), and tripotassium phosphate (1073.16 mg, 5.06 mmol) in dry 1,4-dioxane (5.5 mL) was stirred at 90 °C for 4 hrs in a sealed vial. The reaction mixture was partitioned between H2O and EtOAc, the phases were separated, and the aqueous layer was extracted with EtOAc (2x). The combined organic phases were washed with brine (1x), dried over anhydrous Na2SO4 and evaporated to dryness. The material was purified by flash silica gel chromatography using a 0-40% EtOAc/cyclohexane gradient eluent to afford the title compound (95 mg, 21%) as a white solid. 'H NMR (400 MHz, DMSO-d6) δ 9.92 (1 H, br. s.) 8.69 (1 H, s) 8.21 (1 H, s) 8.07 (1 H, d, J=0.66 Hz) 7.72 - 8.05 (1 H, m) 7.52 (1 H, s) 7.00 (1 H, s) 2.22 (3 H, s). MS-ESI (m/z) calc’d for C12H11F2N4O [M+H]+: 265.1, Found 265.1.
  • 2
  • [ 1000343-69-0 ]
  • [ 1082042-15-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: anhydrous potassium acetate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 12 h / 20 - 120 °C / Inert atmosphere 2: sodium peroxoborate tetrahydrate / tetrahydrofuran; lithium hydroxide monohydrate / 0.83 h / 20 - 50 °C
  • 3
  • [ 1082042-15-6 ]
  • [ 1315479-99-2 ]
  • [ 2803902-93-2 ]
YieldReaction ConditionsOperation in experiment
97% With (tributylphosphoranylidene)acetonitrile In toluene at 20 - 110℃; for 12h; Inert atmosphere; 280.3 Step 3: 5-((5-Methyl-lH-indazol-6-yl)oxy)-5,6, 7,8-tetrahydronaphthalene-2-carbonitrile A mixture of 5 -methyl- l//-indazol-6-ol (200 mg, 1.35 mmol), 5-hydroxy-5, 6,7,8- tetrahydronaphthalene-2-carbonitrile (233.81 mg, 1.35 mmol), and (tributylphosphoranylidene)acetonitrile (651.59 mg, 2.70 mmol) in toluene (3 mL) was degassed and purged with N2 (3x) at 20 °C. The mixture was then stirred at 110 °C for 12 hrs under an N2 atmosphere. The mixture was concentrated to give a residue that was purified by silica gel column chromatography using a 0-26% EtOAc/petroleum ether gradient eluent to afford the title compound (400 mg, 97%) as a brown solid. 'H NMR (400 MHz, CDCh) 8 7.91 - 7.96 (m, 1 H), 7.52 (s, 1 H), 7.47 - 7.50 (m, 3 H), 7.02 (s, 1 H), 5.44 (t, J=5.38 Hz, 1 H), 2.92 - 3.01 (m, 1 H), 2.80 - 2.89 (m, 1 H), 2.25 (s, 3 H), 2.15 - 2.21 (m, 2 H), 2.00 - 2.04 (m, 1 H), 1.85 - 1.94 (m, 1 H). MS-ESI (m/z) calc’d for C19H18N3O [M+H]+: 304.1. Found 304.3.
97% With (tributylphosphoranylidene)acetonitrile In toluene at 20 - 110℃; for 12h; Inert atmosphere; 280.3 Step 3: 5-((5-Methyl-lH-indazol-6-yl)oxy)-5,6, 7,8-tetrahydronaphthalene-2-carbonitrile A mixture of 5 -methyl- l//-indazol-6-ol (200 mg, 1.35 mmol), 5-hydroxy-5, 6,7,8- tetrahydronaphthalene-2-carbonitrile (233.81 mg, 1.35 mmol), and (tributylphosphoranylidene)acetonitrile (651.59 mg, 2.70 mmol) in toluene (3 mL) was degassed and purged with N2 (3x) at 20 °C. The mixture was then stirred at 110 °C for 12 hrs under an N2 atmosphere. The mixture was concentrated to give a residue that was purified by silica gel column chromatography using a 0-26% EtOAc/petroleum ether gradient eluent to afford the title compound (400 mg, 97%) as a brown solid. 'H NMR (400 MHz, CDCh) 8 7.91 - 7.96 (m, 1 H), 7.52 (s, 1 H), 7.47 - 7.50 (m, 3 H), 7.02 (s, 1 H), 5.44 (t, J=5.38 Hz, 1 H), 2.92 - 3.01 (m, 1 H), 2.80 - 2.89 (m, 1 H), 2.25 (s, 3 H), 2.15 - 2.21 (m, 2 H), 2.00 - 2.04 (m, 1 H), 1.85 - 1.94 (m, 1 H). MS-ESI (m/z) calc’d for C19H18N3O [M+H]+: 304.1. Found 304.3.
  • 4
  • [ 2417226-02-7 ]
  • [ 1082042-15-6 ]
  • [ 2803901-32-6 ]
YieldReaction ConditionsOperation in experiment
53% With tripotassium phosphate tribasic; copper (I) iodide; trans-N,N’-dimethylcyclohexane-1,2-diamine In 1,4-dioxane at 90℃; for 2h; Sealed tube; 64.3 In a sealed vial, a mixture of 5-methyl-17/-indazol-6-ol (120.0 mg, 0.81 mmol), 1- (bicyclo[l.l.l]pentan-l-yl)-4-iodo-17/-pyrazole (231.7 mg, 0.89 mmol), (1R,2R)-N1,N2- dimethylcyclohexane-l,2-diamine (57.6 mg, 0.40 mmol), copper (I) iodide (30.85 mg, 0.160 mmol) and tripotassium phosphate (515.12 mg, 2.43 mmol) in dry 1,4-dioxane (2.2 mL) was stirred at 90 °C for 2 hrs. The reaction mixture was partitioned between H2O and EtOAc, the phases were separated, the aqueous layer was extracted with EtOAc (2x) and the combined organic phases were washed with brine (lx), dried over anhydrous Na2SO4 and evaporated to dryness. The material was purified by flash silica gel chromatography using a 0-40% EtOAc/cyclohexane gradient eluent to afford the title compound (120 mg, 53%) as a yellow solid. 'H NMR (400 MHz, DMSO-d6) δ 9.83 (1 H, br. s.) 8.22 (1 H, d, J=0.66 Hz) 8.00 (1 H, d, J=0.88 Hz) 7.83 (1 H, d, J=0.66 Hz) 7.49 (1 H, s) 6.96 (1 H, s) 2.67 (1 H, s) 2.30 (6 H, s) 2.22 (3 H, s). MS-ESI (m/z) calc’d for C16H17N4O [M+H]+: 281.1. Found 281.1.
53% With tripotassium phosphate tribasic; copper (I) iodide; trans-N,N’-dimethylcyclohexane-1,2-diamine In 1,4-dioxane at 90℃; for 2h; Sealed tube; 64.3 In a sealed vial, a mixture of 5-methyl-17/-indazol-6-ol (120.0 mg, 0.81 mmol), 1- (bicyclo[l.l.l]pentan-l-yl)-4-iodo-17/-pyrazole (231.7 mg, 0.89 mmol), (1R,2R)-N1,N2- dimethylcyclohexane-l,2-diamine (57.6 mg, 0.40 mmol), copper (I) iodide (30.85 mg, 0.160 mmol) and tripotassium phosphate (515.12 mg, 2.43 mmol) in dry 1,4-dioxane (2.2 mL) was stirred at 90 °C for 2 hrs. The reaction mixture was partitioned between H2O and EtOAc, the phases were separated, the aqueous layer was extracted with EtOAc (2x) and the combined organic phases were washed with brine (lx), dried over anhydrous Na2SO4 and evaporated to dryness. The material was purified by flash silica gel chromatography using a 0-40% EtOAc/cyclohexane gradient eluent to afford the title compound (120 mg, 53%) as a yellow solid. 'H NMR (400 MHz, DMSO-d6) δ 9.83 (1 H, br. s.) 8.22 (1 H, d, J=0.66 Hz) 8.00 (1 H, d, J=0.88 Hz) 7.83 (1 H, d, J=0.66 Hz) 7.49 (1 H, s) 6.96 (1 H, s) 2.67 (1 H, s) 2.30 (6 H, s) 2.22 (3 H, s). MS-ESI (m/z) calc’d for C16H17N4O [M+H]+: 281.1. Found 281.1.
  • 5
  • [ 1082042-15-6 ]
  • [ 125114-88-7 ]
  • [ 2803902-94-3 ]
YieldReaction ConditionsOperation in experiment
14% With (tributylphosphoranylidene)acetonitrile In toluene at 20 - 110℃; for 2h; Inert atmosphere; 281.3 Step 3: 1-((5-Methyl-1H-indazol-6-yl)oxy)-2,3-dihydro-1H-indene-5-carbonitrile To a solution of 1-hyd -carbonitrile (75 mg,471.15 umol) in toluene (3 mL) were added (tributylphosphoranylidene)acetonitrile (227.43 mg, 942.30 umol) and 5-methyl-1H-indazol-6-ol (62.83 mg, 424.04 umol) at 20 °C. The mixture was then stirred at 110 °C for 2 hrs under an N2 atmosphere. The reaction mixture was concentrated under reduced pressure to remove solvent. The residue was purified by preparative TLC (SiO2, petroleum ether / EtOAc= 1/2, Rf = 0.4) to afford the title compound (20 mg, 14%) as a white solid.1H NMR (400 MHz, CDCl3) δ 7.97 (s, 1H), 7.62 (s, 1H), 7.54- 7.58 (m, 2H), 7.51 (s, 1H), 7.03 (s, 1H), 5.82 (t, J=6.17 Hz, 1H), 3.17-3.24 (m, 1H), 2.99-3.06 (m, 1H), 2.73-2.81 (m, 1H), 2.26-2.31 (m, 1H), 2.24 (s, 3H). MS-ESI (m/z) calc’d for C18H16N3O [M+H]+: 290.1. Found 290.3.
14% With (tributylphosphoranylidene)acetonitrile In toluene at 20 - 110℃; for 2h; Inert atmosphere; 281.3 Step 3: 1-((5-Methyl-1H-indazol-6-yl)oxy)-2,3-dihydro-1H-indene-5-carbonitrile To a solution of 1-hyd -carbonitrile (75 mg,471.15 umol) in toluene (3 mL) were added (tributylphosphoranylidene)acetonitrile (227.43 mg, 942.30 umol) and 5-methyl-1H-indazol-6-ol (62.83 mg, 424.04 umol) at 20 °C. The mixture was then stirred at 110 °C for 2 hrs under an N2 atmosphere. The reaction mixture was concentrated under reduced pressure to remove solvent. The residue was purified by preparative TLC (SiO2, petroleum ether / EtOAc= 1/2, Rf = 0.4) to afford the title compound (20 mg, 14%) as a white solid.1H NMR (400 MHz, CDCl3) δ 7.97 (s, 1H), 7.62 (s, 1H), 7.54- 7.58 (m, 2H), 7.51 (s, 1H), 7.03 (s, 1H), 5.82 (t, J=6.17 Hz, 1H), 3.17-3.24 (m, 1H), 2.99-3.06 (m, 1H), 2.73-2.81 (m, 1H), 2.26-2.31 (m, 1H), 2.24 (s, 3H). MS-ESI (m/z) calc’d for C18H16N3O [M+H]+: 290.1. Found 290.3.
  • 6
  • [ 1463055-25-5 ]
  • [ 1082042-15-6 ]
YieldReaction ConditionsOperation in experiment
43% With sodium peroxoborate tetrahydrate In tetrahydrofuran; lithium hydroxide monohydrate at 20 - 50℃; for 0.833333h; 280.2; 281.2 Step 2: 5 -Methyl- lH-indazol-6-ol To a solution of 5-methyl-6-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)- 1H- indazole (2.6 g, 6.31 mmol) in THF (20 mL) and H2O (20 mL) was added sodium perborate tetrahydrate (2.91 g, 18.92 mmol) at 20 °C. The mixture was then stirred at 50 °C for 50 min. The reaction mixture was concentrated under reduced pressure to remove solvent. The residue was diluted with H2O and extracted with EtOAc (3x). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by silica gel chromatography using a 0-50% EtOAc/petroleum ether gradient eluent to afford the title compound (409.2 mg, 43%) as a pale yellow solid. MS-ESI (m/z) calc’d for C8H9N2O [M+H]+:149.1. Found 149.3.
43% With sodium peroxoborate tetrahydrate In tetrahydrofuran; lithium hydroxide monohydrate at 20 - 50℃; for 0.833333h; 280.2; 281.2 Step 2: 5 -Methyl- lH-indazol-6-ol To a solution of 5-methyl-6-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)- 1H- indazole (2.6 g, 6.31 mmol) in THF (20 mL) and H2O (20 mL) was added sodium perborate tetrahydrate (2.91 g, 18.92 mmol) at 20 °C. The mixture was then stirred at 50 °C for 50 min. The reaction mixture was concentrated under reduced pressure to remove solvent. The residue was diluted with H2O and extracted with EtOAc (3x). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by silica gel chromatography using a 0-50% EtOAc/petroleum ether gradient eluent to afford the title compound (409.2 mg, 43%) as a pale yellow solid. MS-ESI (m/z) calc’d for C8H9N2O [M+H]+:149.1. Found 149.3.
  • 7
  • [ 1082042-15-6 ]
  • [ 2803894-42-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trans-N,N’-dimethylcyclohexane-1,2-diamine; copper (I) iodide; tripotassium phosphate tribasic / 1,4-dioxane / 2 h / 90 °C / Sealed tube 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1 h / 20 °C
  • 8
  • [ 1082042-15-6 ]
  • [ 2803894-46-2 ]
  • [ 2803894-44-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trans-N,N’-dimethylcyclohexane-1,2-diamine; copper (I) iodide; tripotassium phosphate tribasic / 1,4-dioxane / 2 h / 90 °C / Sealed tube 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1 h / 20 °C 3: isopropylamine / ethanol; hexane / Resolution of racemate
  • 9
  • [ 1082042-15-6 ]
  • [ 2803900-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (tributylphosphoranylidene)acetonitrile / toluene / 12 h / 20 - 110 °C / Inert atmosphere 2: copper (I) iodide; tripotassium phosphate tribasic; cis-N,N'-dimethyl-1,2-diaminocyclohexane / 1,4-dioxane / 12 h / 20 - 105 °C / Inert atmosphere
  • 10
  • [ 1082042-15-6 ]
  • [ 2803900-29-8 ]
  • [ 2803900-30-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (tributylphosphoranylidene)acetonitrile / toluene / 12 h / 20 - 110 °C / Inert atmosphere 2: copper (I) iodide; tripotassium phosphate tribasic; cis-N,N'-dimethyl-1,2-diaminocyclohexane / 1,4-dioxane / 12 h / 20 - 105 °C / Inert atmosphere 3: ammonium hydroxide / ethanol / Resolution of racemate
  • 11
  • [ 1082042-15-6 ]
  • [ 2803900-31-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (tributylphosphoranylidene)acetonitrile / toluene / 12 h / 20 - 110 °C / Inert atmosphere 2: copper (I) iodide; tripotassium phosphate tribasic; cis-N,N'-dimethyl-1,2-diaminocyclohexane / 1,4-dioxane / 12 h / 20 - 105 °C / Inert atmosphere
  • 12
  • [ 1082042-15-6 ]
  • [ 2803900-33-4 ]
  • [ 2803900-32-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (tributylphosphoranylidene)acetonitrile / toluene / 12 h / 20 - 110 °C / Inert atmosphere 2: copper (I) iodide; tripotassium phosphate tribasic; cis-N,N'-dimethyl-1,2-diaminocyclohexane / 1,4-dioxane / 12 h / 20 - 105 °C / Inert atmosphere 3: ammonium hydroxide / isopropanol / Resolution of racemate
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