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CAS No. : | 50593-24-3 | MDL No. : | MFCD03305455 |
Formula : | C8H9N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PYOFNPHTKBSXOM-UHFFFAOYSA-N |
M.W : | 147.18 | Pubchem ID : | 2768032 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 45.4 |
TPSA : | 43.84 Ų |
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) : | -6.57 cm/s |
Log Po/w (iLOGP) : | 1.24 |
Log Po/w (XLOGP3) : | 0.89 |
Log Po/w (WLOGP) : | 1.16 |
Log Po/w (MLOGP) : | 0.84 |
Log Po/w (SILICOS-IT) : | 0.71 |
Consensus Log Po/w : | 0.97 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.92 |
Solubility : | 1.77 mg/ml ; 0.0121 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.4 |
Solubility : | 5.92 mg/ml ; 0.0402 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.09 |
Solubility : | 1.19 mg/ml ; 0.00807 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.35 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With iron; ammonium chloride In ethanol; water at 80℃; for 1 h; | Step 2: Preparation of l-methyl-lH-indazol-5-amine Iron powder (5.04 g, 0.0903 mol) is added portionwise to a solution of l-methyl-5- nitro-lH-indazole (4.00 g, 0.0226 mol) and ammonium chloride (12.1 g, 0.225 mol) in ethanol (225 mL) and water (100 mL) at 8O0C. The mixture is stirred and heated for Ih, diluted with dichloromethane (500 mL) and filtered. The organic layer is separated, dried (Mg2SO4) and evaporated to afford the title compound (3.29 g, 99percent); HPLC (SYMMETRY C18 3.5 μM, 4.6 x 30 mm column; gradient elution 2percent-98percent MeCN with 0.1percent TFA over 10 min; 2 mL/min rate): retention time = 1.06 min; MS for C1OHnN3 m/z 147.2(M+H)+. |
71% | With hydrogenchloride; iron In ethanol; waterReflux | Iron (3.62 g, 64.7 mmol) and concentrated hydrochloric acid (0.1 mL) were added to ethanol/water (20 mL/20 mL), and refluxed for 1 hour. The mixed reaction solution was added with l-methyl-5-nitro-lH-indazole (2.29 g, 12.9 mmol) obtained in above, and further refluxed for 3 hours or more. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with chloroform/2-propanol = 4/l(v/v). The filtrate obtained was distilled under reduced pressure, and dissolved in chloroform/2-propanol = 4/1 (v/v). The organic layer was washed with an aqueous solution of sodium bicarbonate and brine. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (1.35 g, 71percent). -NMR Spectrum (300 MHz, OMSO-d6): δ 7.65 (d, 1H), 7.31 (d, 1H), 6.80 (d, 1H), 6.71 (d, 1H), 4.78 (s, 2H), 3.89 (s, 3H) MS(ESI+, m/z): 148 [M+H]+ |
71% | With hydrogenchloride; iron In ethanol; waterReflux | Iron (3.62 g, 64.7 mmol) and concentrated hydrochloric acid (0.1 mL) were added to ethanol/water (20 mL/20 mL), and refluxed for 1 hour. The mixed reaction solution was added with 1-methyl-5-nitro-1H-indazole (2.29 g, 12.9 mmol) obtained in <Step 1> above, and further refluxed for 3 hours or more. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with chloroform/2-propanol=4/1(v/v). The filtrate obtained was distilled under reduced pressure, and dissolved in chloroform/2-propanol=4/1 (v/v). The organic layer was washed with an aqueous solution of sodium bicarbonate and brine. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (1.35 g, 71percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 7.65 (d, 1H), 7.31 (d, 1H), 6.80 (d, 1H), 6.71 (d, 1H), 4.78 (s, 2H), 3.89 (s, 3H) MS (ESI+, m/z): 148 [M+H]+ |
18% | With ammonium chloride; acetic acid; zinc In ethanol; water; ethyl acetate at 20℃; for 1 h; | Zinc powder (194 mmol), ammonium chloride (388 mmol), and acetic acid (33.3 mmol) were added, successively, to a solution of l-methyl-5-nitro-1H-indazole (19.1 mmol) in ethanol (50 mL), water (20 mL), and ethyl acetate (5 mL) and the resulting suspension was maintained at rt for 1 h. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was purified by Flash chromatography (5/1 petroleum ether/ethyl acetate) to provide 1 -methyl- 1H-indazol-5-amine in 18percent yield as a brown solid. |
18% | With ammonium chloride; acetic acid; zinc In ethanol; water; ethyl acetate at 20℃; for 1 h; | 2. Synthesis of 1 -methyl- lH-indazol-5-amine.Zinc powder (194 mmol), ammonium chloride (388 mmol), and acetic acid (33.3 mmol) were added, successively, to a solution of l-methyl-5-nitro-lH-indazole (19.1 mmol) in ethanol (50 mL), water (20 mL), and ethyl acetate (5 mL) and the resulting suspension was maintained at rt for 1 h. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was purified by Flash chromatography (5/1 petroleum ether/ethyl acetate) to provide 1- methyl-lH-indazol-5-amine in 18percent yield as a brown solid. |
18% | With ammonium chloride; acetic acid; zinc In ethanol; water; ethyl acetate at 20℃; for 1 h; | 2. Synthesis of l-methyl-lH-indazol-5-amine.Zinc powder (194 mmol), ammonium chloride (388 mmol), and acetic acid (33.3 mmol) were added, successively, to a solution of l-methyl-5-nitro-lH-indazole (19.1 mmol) in ethanol (50 mL), water (20 mL), and ethyl acetate (5 mL) and the resulting suspension was maintained at rt for 1 h. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was purified by Flash chromatography (5/1 petroleum ether/ethyl acetate) to provide 1- methyl-lH-indazol-5-amine in 18percent yield as a brown solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | Stage #1: With sulfuric acid; sodium nitrite In water at 0℃; for 0.166667 h; Stage #2: With sodium iodide In water at 0 - 90℃; for 0.333333 h; |
Method s: 5-iodo-l-methyl-lH-indazole; [00138] To l-Methyl-lH-indazol-5-amine (500 mg, 3.40 mmol) in a mixture of concentrated sulfuric acid (1.3 ml) and water <n="49"/>(5.5 ml) cooled down to 00C, was added dropwise a solution of sodium nitrite (258 mg, 3.74 mmol) in water (0.5 ml) . The reaction mixture was stirred at 00C for 10 minutes then added dropwise to a solution of sodium iodide (1.5 g) in water (4.5 ml) cooled to 00C. After complete addition, the reaction mixture was heated to 900C for an additional 20 minutes. The resultant mixture was basified with a diluted solution of sodium hydroxide and extracted with ethylacetate . The organic phase was washed further with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography eluting with 20percent EtOAc in petroleum ether to afford the title compound (475 mg, 54percent yield). 1H NMR (DMSO D6, 400 MHz) 4.03 (3H, s) , 7.52 (IH, d) , 7.63 (IH, dd) , 7.99 (IH, s), 8.17 (IH, s) . |
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