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Chemical Structure| 15579-15-4
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Product Details of [ 15579-15-4 ]

CAS No. :15579-15-4 MDL No. :MFCD01938124
Formula : C7H6N2O Boiling Point : -
Linear Structure Formula :- InChI Key :ZHDXWEPRYNHNDC-UHFFFAOYSA-N
M.W : 134.14 Pubchem ID :101438
Synonyms :

Calculated chemistry of [ 15579-15-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 38.12
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) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.63
Log Po/w (XLOGP3) : 1.33
Log Po/w (WLOGP) : 1.27
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : 1.59
Consensus Log Po/w : 1.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.18
Solubility : 0.895 mg/ml ; 0.00668 mol/l
Class : Soluble
Log S (Ali) : -1.96
Solubility : 1.48 mg/ml ; 0.011 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.3
Solubility : 0.668 mg/ml ; 0.00498 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 15579-15-4 ]

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 [ 15579-15-4 ]

* 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 [ 15579-15-4 ]
  • Downstream synthetic route of [ 15579-15-4 ]

[ 15579-15-4 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 94444-96-9 ]
  • [ 15579-15-4 ]
YieldReaction ConditionsOperation in experiment
71% With boron tribromide In dichloromethane at 20℃; for 10 h; A methylene chloride solution of boron tribromide (18.5 ml, 18.5 mmol) was added to a solution of 5-methoxy-1H-indazole (1.24 g, 8.40 mmol) in methylene chloride (84 ml) at 0°C and stirred at room temperature for 10 hours. Then, water was poured into the reaction solution in an ice-water bath, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol = 96/4) to obtain 1H-indazol-5-ol (877 mg, 71percent).1H-NMR (DMSO-d6) δ; 6.88 (1H, dd, J=8.8, 2.2Hz), 6.96 (1H, d, J=2.2Hz), 7.34 (1H, d, J=8.8Hz), 7.84 (1H, s).
Reference: [1] Patent: EP1403255, 2004, A1, . Location in patent: Page 44
  • 2
  • [ 19335-11-6 ]
  • [ 15579-15-4 ]
Reference: [1] Journal of the Chemical Society, 1955, p. 2412,2419
[2] Bulletin de la Societe Chimique de France, 1950, p. 466,476
[3] Patent: US2006/58361, 2006, A1, . Location in patent: Page/Page column 34-35
  • 3
  • [ 543-87-3 ]
  • [ 2835-99-6 ]
  • [ 144-55-8 ]
  • [ 15579-15-4 ]
Reference: [1] Patent: EP1256574, 2002, A1,
  • 4
  • [ 36174-07-9 ]
  • [ 15579-15-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 1, p. 350 - 364
  • 5
  • [ 2835-99-6 ]
  • [ 15579-15-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 1, p. 350 - 364
  • 6
  • [ 102-50-1 ]
  • [ 15579-15-4 ]
Reference: [1] Patent: EP1403255, 2004, A1,
  • 7
  • [ 5401-94-5 ]
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Reference: [1] Journal of the Chemical Society, 1955, p. 2412,2419
  • 8
  • [ 15579-15-4 ]
  • [ 478834-25-2 ]
YieldReaction ConditionsOperation in experiment
86% With N-chloro-succinimide In tetrahydrofuran at 20 - 50℃; for 8 h; To a solution of the 1H-indazol-5-ol (1.60 g, 0.0119 mol) obtained in Reference Example 4 in tetrahydrofuran (50 ml) was added N-chlorosuccinimide (1.59 g, 0.0119 mol) at room temperature. After 1 hour, the mixture thus obtained was heated to 40°C, and after another 2 hour, the mixture was heated to 50°C. After 5 hours, the reaction solution was poured into water (100 ml) and extracted with ethyl acetate (100 ml x 3). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 4-chloro-1H-indazol-5-ol (1.7365 g, 86percent).1H-NMR (DMSO-d6) δ; 7.09 (1H, d, J=8.8Hz), 7.33 (1H, d, J=8.8Hz), 7.90 (1H, s), 9.71 (1H, s), 13.10 (1H, s).
Reference: [1] Patent: EP1403255, 2004, A1, . Location in patent: Page 120
  • 9
  • [ 15579-15-4 ]
  • [ 100-39-0 ]
  • [ 78299-75-9 ]
YieldReaction ConditionsOperation in experiment
46% With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; -(Benzyloxy)-l H-indazole-152-4820V.1 A degassed DMF (30 mL) suspension of lH-indazol-5-ol (1.0 g, 7.5 mmol) and K2CO3 (2.0 g, 15 mmol) was treated with benzylbromide (0.98 mL, 8.20 mmol) at 0 oC. The reaction was stirred with cooling for 2 h and then allowed slowly to warm to rt overnight. Later the reaction mixture was diluted with H20 ( 100 mL). A precipitate was collected filtration, rinsed with H20 then suspended in Et20 and isolated by a filtration to provide the title compound as white solid (0.77 g, 46 percent). NMR (400 MHz, METHANOLS) δ ppm 7.93 (s, 1 H), 7.43 - 7.50 (m, 3 H), 7.36 - 7.42 (m, 2 H), 7.33 (d, 7=7.03 Hz, 1 H), 7.26 (s, 1 H), 7.15 (d, 7=8.78 Hz, 1 H), 5.12 (s, 2 H); MS ESI 225.0 [M + H]+, calc for [C,4Hi2N20+H]+ 225.1.
46% With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; A degassed DMF (30mL) suspension of 1H-indazol-5-ol (1.0g, 7.5mmol) and K2CO3 (2.0g, 15mmol) was treated with benzylbromide (0.98mL, 8.20mmol) at 0°C. The reaction was stirred with cooling for 2h and then allowed slowly to warm to rt overnight. Later the reaction mixture was diluted with H2O (100mL). A precipitate was collected filtration, rinsed with H2O then suspended in Et2O and isolated by a filtration to provide the title compound as white solid (0.77g, 46percent). 1H NMR (400MHz, CD3OD) δ ppm 7.93 (s, 1H), 7.43–7.50 (m, 3H), 7.36–7.42 (m, 2H), 7.33 (d, J=7.03Hz, 1H), 7.26 (s, 1H), 7.15 (d, J=8.78Hz, 1H), 5.12 (s, 2H); MS ESI 225.0 [M+H]+, calc for [C14H12N2O+H]+ 225.1.
38% With potassium carbonate In DMF (N,N-dimethyl-formamide) at 40℃; for 2 h; Benzyl bromide (0.089 ml, 0.745 mmol) and potassium carbonate (103 mg, 0.745 mmol) were added to a solution of the 1H-indazol-5-ol (100 mg, 0.745 mmol) obtained in Reference Example 4 in N,N-dimethylformamide (2 ml), and the resulting mixture was heated to 40°C. After 2 hours, the mixture was poured into water (20 ml) and extracted with ethyl acetate (20 ml x 2). The organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 5-(benzyloxy)-1H-indazole (63 mg, 38percent). Melting point: 179-181°C
Reference: [1] Patent: WO2011/123937, 2011, A1, . Location in patent: Page/Page column 152-153
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4968 - 4997
[3] Patent: EP1403255, 2004, A1, . Location in patent: Page 97
  • 10
  • [ 15579-15-4 ]
  • [ 1254473-64-7 ]
Reference: [1] Patent: US2012/83511, 2012, A1,
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