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[ CAS No. 192945-49-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 192945-49-6
Chemical Structure| 192945-49-6
Chemical Structure| 192945-49-6
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Product Details of [ 192945-49-6 ]

CAS No. :192945-49-6 MDL No. :MFCD07371610
Formula : C9H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :MEXWKIOTIDFYPN-UHFFFAOYSA-N
M.W : 176.17 Pubchem ID :6623327
Synonyms :

Calculated chemistry of [ 192945-49-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.37
TPSA : 54.98 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) : -6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.21
Log Po/w (XLOGP3) : 1.41
Log Po/w (WLOGP) : 1.35
Log Po/w (MLOGP) : 1.04
Log Po/w (SILICOS-IT) : 1.84
Consensus Log Po/w : 1.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.2
Solubility : 1.11 mg/ml ; 0.0063 mol/l
Class : Soluble
Log S (Ali) : -2.17
Solubility : 1.19 mg/ml ; 0.00678 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.98
Solubility : 0.183 mg/ml ; 0.00104 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.5

Safety of [ 192945-49-6 ]

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 [ 192945-49-6 ]

* 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.

  • Upstream synthesis route of [ 192945-49-6 ]
  • Downstream synthetic route of [ 192945-49-6 ]

[ 192945-49-6 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 18583-89-6 ]
  • [ 192945-49-6 ]
YieldReaction ConditionsOperation in experiment
69% With acetic acid; sodium nitrite In water Methyl-3-amino-2-methyl benzoate (0.3 g, 1.96 mmol) was stirred in aqueous NaNO2 (0.62 g, 2 mmol) followed by addition of 7 mL dilute glacial acetic acid in water (7 mL, 3 mmol) (0.2:10). The reaction mixture was allowed to stir for 4-6 hrs. The mixture was then extracted with EtOAc and washed with water (2.x.10 mL). The organic layer was dried over Na2SO4, concentrated and subjected to column chromatography to obtain yellow powder. The yield was 0.22 g, 69percent; m.p. 153-155° C. 1H NMR (400 MHz CDCl3, TMS, ppm) δ 2.55 (s, 3H), 7.37 (t, 1H, J=14.32 Hz), 7.53 (s, 1H), 7.67 (d, 1H, J=8.12 Hz), 7.82 (d, 1H, J=8.16 Hz), 9.79 (s, 1H).
59%
Stage #1: With ammonium tetrafluoroborate; sodium nitrite In water at 0℃;
Stage #2: With 18-crown-6 ether; potassium acetate In chloroform at 20℃; for 2 h; Inert atmosphere
Reference Example 1
methyl 1H-indazole-4-carboxylate
A mixture of methyl 3-amino-o-toluate (100 g, 605 mmol), a solution of ammonium tetrafluoroborate (83.0 g, 787 mmol) in water (600 mL) and concentrated hydrochloric acid (121 mL, 3.93 mmol) was cooled to 0°C, and a solution of sodium nitrite (41.8 g, 605 mmol) in water (88 mL) was added dropwise to the mixture over 25 min.
This mixture was stirred for 35 min, and the resulting solid was collected by filtration.
This solid was washed with water, methanol and diethyl ether, dried under nitrogen atmosphere, and added to a solution of potassium acetate (65.4 g, 666 mmol) and 18-crown-6 (4.50 g, 17.0 mmol) in chloroform (1.37 L).
The resulting mixture was stirred at room temperature for 2 hr, and water (700 mL) was added.
The partitioned organic layer was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure.
The residue was triturated with hexane, and collected by filtration to give the title compound (63.0 g, yield 59percent).
1H-NMR (CDCl3) δ: 4.03 (3H, s), 7.47 (1H, dd, 8.4, 7.2 Hz), 7.73 (1H, d, J = 8.4 Hz), 7.96 (1H, d, J = 7.2 Hz), 8.61 (1H, s),
MS (ESI+): 177 (M+H).
Reference: [1] Patent: US2012/130078, 2012, A1, . Location in patent: Page/Page column 4-5
[2] Patent: EP2141150, 2010, A1, . Location in patent: Page/Page column 48
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 1, p. 41 - 58
[4] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 1921 - 1930
[5] Patent: WO2009/108838, 2009, A1, . Location in patent: Page/Page column 104
  • 2
  • [ 677306-38-6 ]
  • [ 18107-18-1 ]
  • [ 192945-49-6 ]
YieldReaction ConditionsOperation in experiment
50% at 20℃; Synthesis of lH-Indazole-4-carboxylic acid methyl ester (18a): To a solution of lH-Indazole-4-carboxylic acid (lOOmg, 0.62 mmol) in 6 mL of methanol-dichloromethane (1 : 1) was added trimethylsilyl diazomethane (2.0 M in ethyl ether) dropwise at room temperature. More trimethylsilyl diazomethane was added until the starting material disappeared. Solvent was removed carefully and the residue was purified by column chromatography (50percent ethyl acetate/hexanes). The product (54 mg, 50percent) was obtained as a colorless solid. MS (ES) M+H expected = 177.1, found = 177.2.
Reference: [1] Patent: WO2007/51062, 2007, A2, . Location in patent: Page/Page column 127-128
[2] Patent: WO2011/49917, 2011, A1, . Location in patent: Page/Page column 42-43
[3] Patent: WO2009/134666, 2009, A1, . Location in patent: Page/Page column 50
  • 3
  • [ 1388057-36-0 ]
  • [ 192945-49-6 ]
Reference: [1] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 1921 - 1930
  • 4
  • [ 1975-50-4 ]
  • [ 192945-49-6 ]
Reference: [1] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 1921 - 1930
  • 5
  • [ 59382-59-1 ]
  • [ 192945-49-6 ]
Reference: [1] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 1921 - 1930
  • 6
  • [ 192945-49-6 ]
  • [ 677306-38-6 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: With sodium hydroxide In ethanol; waterHeating / reflux
Stage #2: With hydrogenchloride In water
A solution of sodium hydroxide (1.70 g, 42.6 mmol) in water (25 ml) was added to a solution of methyl 1H-indazole-4-carboxylate (Description 9,2. 50 g, 14.2 mmol) in ethanol (50 ml) and the resulting mixture heated at reflux overnight. The ethanol was removed from the cooled reaction mixture by evaporation and the aqueous phase then acidified by the addition of conc. HCI. The resultant precipitate was collected by filtration and dried under vacuum to give the title compound as an orange solid (2.0 g, 87percent). H NMR (400 MHZ, DMSO-D6) 8 7. 48 (lH, m), 7.81 (1H, dd, J7.4 and 0. 7), 7.85 (1H, dd, J 8. 4 and 0.8), 8.42 (1H, d, J0.8), 9.20 (1H, br s).
56%
Stage #1: With water; sodium hydroxide In methanol for 6 h; Reflux
Stage #2: With hydrogenchloride In waterCooling with ice
To a stirred solution of indazole-4-carboxylic acid methyl ester (0.3 g 1.7 mmol) in 10 mL methanol, NaOH (0.27 g, 6.8 mmol) in 2 mL of water was added and the reaction mixture was refluxed for 6 h. The reaction was cooled and the solvent was evaporated under reduced pressure and 2 mL of water was added. The solution was cooled on ice and compound was precipitated by adding concentrated HCl drop-wise. The resulting yellow precipitate was collected and washed with acidic water and dried (0.15 g, 56percent). m.p. 223-226° C. 1H NMR (400 MHz, DMSO-d6, TMS) δ 10.20 (bs, 2H), 7.75 (d, 1H), 7.60 (d, 1H), 7.35 (d, 1H), 7.28 (t, 1H).
Reference: [1] Patent: WO2005/28445, 2005, A2, . Location in patent: Page/Page column 29
[2] Patent: US2012/130078, 2012, A1, . Location in patent: Page/Page column 6
  • 7
  • [ 192945-49-6 ]
  • [ 709608-85-5 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With diisobutylaluminium hydride In tetrahydrofuran at 0℃;
Stage #2: With water; Rochelle's salt In tetrahydrofuran at 20℃;
Synthesis of (lH-Indazol-4-yl)-methanol (18b): The ester obtained above (40 mg, 0.23 mmol) was dissolved in 1 mL of THF and cooled to 00C. A solution of DEAL in THF (1.0 M, 2.3 mL, 2.3 mmol) was added dropwise. More DIBAL was added until the starting material disappeared. The reaction was then quenched with saturated potassium sodium tartrate solution and warmed up to room temperature. The reaction mixture was extracted with ethyl acetate. The organic layers were combined and dried over MgSO4. Solvent was then removed and the residue was purified by column chromatography (75percent ethyl acetate/hexanes). The product (20 mg, 60percent) was obtained as a white solid. MS (ES) M+H expected = 149.1, found = 149.1.
Reference: [1] Patent: WO2007/51062, 2007, A2, . Location in patent: Page/Page column 126-127
  • 8
  • [ 192945-49-6 ]
  • [ 74-88-4 ]
  • [ 1071428-42-6 ]
Reference: [1] Patent: EP2141147, 2010, A1, . Location in patent: Page/Page column 20
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