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CAS No. : | 54535-00-1 | MDL No. : | MFCD11846959 |
Formula : | C8H10N4O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SHYHYVCNCNAWHV-UHFFFAOYSA-N |
M.W : | 178.19 | Pubchem ID : | 44141733 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.38 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.84 |
TPSA : | 63.31 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.35 cm/s |
Log Po/w (iLOGP) : | 1.66 |
Log Po/w (XLOGP3) : | 0.05 |
Log Po/w (WLOGP) : | 0.08 |
Log Po/w (MLOGP) : | -0.03 |
Log Po/w (SILICOS-IT) : | 0.65 |
Consensus Log Po/w : | 0.48 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.42 |
Solubility : | 6.73 mg/ml ; 0.0378 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.93 |
Solubility : | 20.8 mg/ml ; 0.117 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.94 |
Solubility : | 2.03 mg/ml ; 0.0114 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.26 |
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 |
---|---|---|
81% | With acetic acid In ethanol for 1 h; Reflux | Intermediate a3 (3.0 g, 16.0 mmol) was solubilizedin ethanol (36 mL), 2,4-pentandione (1.8 g, 17.0 mmol) andaceticacid (0.3 mL) were added, the mixture was heated to refluxfor 1 h. After that, the mixture was cooled to rt and filterd, washedwith ethanol and the filtrate was concentrated in vacuo, then cooledto 0 C and stirred for 2 h, the resulting precipitate was filtered,washed with ethanol and dried under reduced pressure to yieldthe title compound as a white solid (2.3 g, 81percent).MS[M+H]+m/z: 179. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.7% | for 20 h; Heating / reflux | The title compound was prepared by a slight modification of a reported procedure (Lippman, E.; Becker, V. , Z. CHEM., 1974, 14, 405): A solution of (5-AMINO-1H-1, 2, 4-triazol-3- yl) methanol glycolate (30.7 g, 0.161 mol, from Step 1, above) and 2,4-pentadione (32.3 g, 0.323 mol, 2 equiv) in a mixture of EtOH (750 mL) and AcOH (250 mL) was REFLUXED 20 h. At the beginning the reaction mixture was clear solution, then gradually turned yellow towards the end of the heating period. The solvent was removed under reduced pressure, and the resulting yellow paste triturated with EtOH (100 mL) and stirred for 15 min. The slurry was chilled to 5 C (ice bath) with stirring for 30 min, filtered, and washed with cold (0-5 C) EtOH. The product was dried in vacuo at 25-30 C to give 24 g (83.7percent). H NMR (300 MHZ, DMSO-D6) 8 2. 57 (3H), 2.71 (3H), 4.63 (2H), 5.5 (1H, OH), 7.13 (1H). LC-MS (APCI) CALCD FOR C8HION40 : 178.19 ; found (M+H+) : 179. 1 M/Z |
83.7% | for 20 h; Heating / reflux | The title compound was prepared by a slight modification of a reported procedure (Lippman, E.; Becker, V., Z. Chem., 1974, 14, 405): A solution of (5-amino-1H-1,2,4-triazol-3-yl)methanol glycolate (30.7 g, 0.161 mol, from Step 1, above) and 2,4-pentadione (32.3 g, 0.323 mol, 2 equiv) in a mixture of EtOH (750 mL) and AcOH (250 mL) was refluxed 20 h. At the beginning the reaction mixture was clear solution, then gradually turned yellow towards the end of the heating period. The solvent was removed under reduced pressure, and the resulting yellow paste triturated with EtOH (100 mL) and stirred for 15 min. The slurry was chilled to 5° C. (ice bath) with stirring for 30 min, filtered, and washed with cold (0-5° C.) EtOH. The product was dried in vacuo at 25-30° C. to give 24 g (83.7percent). 1H NMR (300 MHz, DMSO-d6) δ 2.57 (3H), 2.71 (3H), 4.63 (2H), 5.5 (1H, OH), 7.13 (1H). LC-MS (APCI) calcd for C8H10N4O: 178.19; found (M+H+): 179.1 m/z. |
82% | With acetic acid In ethanol for 1 h; Reflux | [442] 88a glycolic acid salt (10.0 g, 52.6 mmol) was dissolved in EtOH (120 mL), and the resultant solution was treated with pentane-2,4-dione (6 mL, 57.8 mmol) and acetic acid (1.0 mL). The mixture was heated to reflux for 1 hr, then cooled to RT, and diluted with DCM (25 mL), followed by addition of Celite (2.5 g). After stirring for 1 hr, the mixture was filtered through a Buchner funnel packed with Celite and rinsed with EtOH. The solution was distilled to 5 vols, then cooled to 0 °C for 1-2 hr. The slurry was filtered and the cake was rinsed with cool EtOH. The solids were dried to provide the product 88d (13.0 g, 82percent). MS calcd: (M+H)+ = 179. MS found: (M+H)+ = 179. |
81.7% | With acetic acid In ethanol for 1 h; Heating / reflux | To a 2L, 3-neck flask was charged glycolate salt of (5-amino-1tf-1 ,2,4-triazol-3-yl)methanol (99.93 g, 0.526 mol), 2,4 pentanedione (0.578 mols, 60 mL), acetic acid (6.70 mL), and EtOH (550 mL). The mixture was heated to a slight reflux. One hour after adding the reagents, the resulting solution was cooled to ambient temperature, and CH2CI2 (500 mL) and Celite (25.03 g) were added. After stirring for 1 h, the mixture was filtered through a 4" Buchner funnel packed with celite (20 g) and rinsed with EtOH (100 mL). The solution was distilled to 5 vols then cooled to 0 °C for 1-2 hours. The slurry was filtered and the cake was rinsed with cold EtOH (2x100 mL). The solids were dried to provide 76.67 g (81.7percent) of the title compound.1H NMR (300 MHz, d6-DMSO): 2.57 (s, 3), 2.71 (d, 3, J=0.8), 4.63 (uneven d, 2, J=5.7), 5.49(t, 1 , J=6.2), 7.13 (d, 1 , J=0.8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | at 20℃; for 4 h; Heating / reflux | To a slurry of (5-AMINO-1H- [1, 2,4] triazol-3-yl)-methanol (9.5 g, 50 mmol) from Step 1 above in acetic acid (200 mL) was added 2,4-pentanedione (5.13 mL, 50 mmol). The mixture was heated to reflux for 4 hours, and then cooled to room temperature. The product was isolated by removing the solvent by rotary evaporation (8.5 g, 95percent yield). MS (ESI) : 179 (M+H). |
95% | for 4 h; Heating / reflux | To a slurry of (5-amino-1H-[1,2,4]triazol-3-yl)-methanol (9.5 g, 50 mmol) from Step 1 above in acetic acid (200 mL) was added 2,4-pentanedione (5.13 mL, 50 mmol). The mixture was heated to reflux for 4 hours, and then cooled to room temperature. The product was isolated by removing the solvent by rotary evaporation (8.5 g, 95percent yield). MS (ESI): 179 (M+H). |
95% | for 4 h; Heating / reflux | To a slurry of (5-amino-1 H-[1,2,4]triazol-3-yl)-methanol (9.5 g, 50 mmol) from step 6 above in acetic acid (200 mL) was added 2,4-pentanedione (5.13 mL, 50 mmol). The mixture was heated to reflux for 4 hours, and then cooled to room temperature. The product was isolated by removing the solvent by rotary evaporation (8.5 g, 95percent yield). MS (ESI): 179 (M+H) |
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