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[ CAS No. 54535-00-1 ] {[proInfo.proName]}

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Chemical Structure| 54535-00-1
Chemical Structure| 54535-00-1
Structure of 54535-00-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 54535-00-1 ]

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 :

Calculated chemistry of [ 54535-00-1 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

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

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.26

Safety of [ 54535-00-1 ]

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:

Application In Synthesis of [ 54535-00-1 ]

* 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 [ 54535-00-1 ]
  • Downstream synthetic route of [ 54535-00-1 ]

[ 54535-00-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 123-54-6 ]
  • [ 54535-00-1 ]
YieldReaction ConditionsOperation 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.
Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 9, p. 2621 - 2631
  • 2
  • [ 63870-39-3 ]
  • [ 123-54-6 ]
  • [ 54535-00-1 ]
YieldReaction ConditionsOperation 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).

Reference: [1] Patent: WO2004/74270, 2004, A2, . Location in patent: Page 300-301
[2] Patent: US2005/176701, 2005, A1, . Location in patent: Page/Page column 144
[3] Organic Process Research and Development, 2006, vol. 10, # 4, p. 814 - 821
[4] Patent: WO2012/83105, 2012, A1, . Location in patent: Page/Page column 102-103
[5] Patent: WO2007/23381, 2007, A1, . Location in patent: Page/Page column 55
  • 3
  • [ 27277-03-8 ]
  • [ 123-54-6 ]
  • [ 54535-00-1 ]
YieldReaction ConditionsOperation 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)
Reference: [1] Patent: WO2004/74270, 2004, A2, . Location in patent: Page 327-328
[2] Patent: US2005/176701, 2005, A1, . Location in patent: Page/Page column 158
[3] Patent: WO2006/18725, 2006, A1, . Location in patent: Page/Page column 104
  • 4
  • [ 55293-96-4 ]
  • [ 54535-00-1 ]
Reference: [1] Organic Process Research and Development, 2014, vol. 18, # 1, p. 45 - 56
  • 5
  • [ 1508308-97-1 ]
  • [ 54535-00-1 ]
Reference: [1] Organic Process Research and Development, 2014, vol. 18, # 1, p. 45 - 56
  • 6
  • [ 87253-62-1 ]
  • [ 54535-00-1 ]
Reference: [1] Patent: WO2015/78836, 2015, A1,
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