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[ CAS No. 22819-07-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 22819-07-4
Chemical Structure| 22819-07-4
Chemical Structure| 22819-07-4
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Product Details of [ 22819-07-4 ]

CAS No. :22819-07-4 MDL No. :MFCD02223232
Formula : C9H10N4 Boiling Point : -
Linear Structure Formula :- InChI Key :QGLMSZQOJZAPSZ-UHFFFAOYSA-N
M.W : 174.20 Pubchem ID :1116697
Synonyms :

Calculated chemistry of [ 22819-07-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 50.24
TPSA : 67.59 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) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.75
Log Po/w (XLOGP3) : 1.6
Log Po/w (WLOGP) : 0.99
Log Po/w (MLOGP) : 0.81
Log Po/w (SILICOS-IT) : 1.65
Consensus Log Po/w : 1.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.42
Solubility : 0.659 mg/ml ; 0.00378 mol/l
Class : Soluble
Log S (Ali) : -2.63
Solubility : 0.408 mg/ml ; 0.00234 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.42
Solubility : 0.0659 mg/ml ; 0.000378 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.0

Safety of [ 22819-07-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 22819-07-4 ]

* 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.

  • Downstream synthetic route of [ 22819-07-4 ]

[ 22819-07-4 ] Synthesis Path-Downstream   1~39

YieldReaction ConditionsOperation in experiment
s. Atkinson et al., Soc. 1954, 4508;
Aminoguanidin-sulfat, Phenylessigsaeure;
  • 2
  • [ 780722-26-1 ]
  • [ 22819-07-4 ]
  • C11H11N7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With hydrogenchloride In water Heating;
  • 3
  • [ 14527-26-5 ]
  • [ 937-39-3 ]
  • [ 22819-07-4 ]
  • 4
  • [ 27807-84-7 ]
  • [ 22819-07-4 ]
  • [ 1029521-10-5 ]
YieldReaction ConditionsOperation in experiment
With acetic acid at 80℃; for 20h; C A solution of 2 g of 4-chloroacetoacetate and 3.45 g of 5-benzyl-1 H-1 ,2,4-triazole-3-amine 60 ml of in AcOH is heated at 80° for 20 hours. On cooling to RT the reaction mixture obtained is diluted with EtOAc and H2O, the organic portion is separated, dried, filtered and concentrated. The residue obtained is triturated with Et2O, filtered and dried. The title compound is obtained. [M+H]+ 274.
  • 5
  • [ 1028843-08-4 ]
  • [ 22819-07-4 ]
  • [ 1029520-80-6 ]
YieldReaction ConditionsOperation in experiment
With acetic acid at 100℃; for 5h; 1 0.675 g of 4-(2,3-Difluorophenylsulfanyl)-3-oxo-butyric acid methyl ester and 0.451 g of 5- benzyl-2H-[1 ,2,4]triazol-3-ylamine are dissolved in 10 nl of AcOH and stirred at 100° for 5 hours. On cooling, the mixture obtained is diluted with 20 ml of EtOAc, washed 2x with 20 ml of H2O/brine and dried. The residue obtained is filtered and solvent is evaporated. The product obtained is stirred with Et2O at RT for 16 hours. A precipitate obtained is filtered off and dried. 2-Benzyl-5-(2,3-difluorophenylsulfanylmethyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ol is obtained. [M+H]+: 385/386
  • 7
  • [ 22819-07-4 ]
  • [ 1431968-87-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 20 °C 2: sodium hydroxide / ethanol; water / 0.33 h / 100 °C
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 5 h / 20 °C 2: sodium hydroxide / ethanol; water / 0.33 h / 100 °C
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 20 °C 2: sodium hydroxide / ethanol; water / 0.33 h / 100 °C
  • 8
  • C4H10N4O [ No CAS ]
  • [ 22819-07-4 ]
YieldReaction ConditionsOperation in experiment
In water at 180℃; Microwave irradiation;
  • 9
  • [ 591246-80-9 ]
  • [ 22819-07-4 ]
YieldReaction ConditionsOperation in experiment
In water at 180℃; Microwave irradiation;
  • 10
  • [ 22819-07-4 ]
  • [ 1431968-83-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5 h / 20 °C 2: sodium hydroxide / ethanol; water / 0.33 h / 100 °C
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 20 °C 2: sodium hydroxide / ethanol; water / 0.33 h / 100 °C
  • 11
  • [ 33513-42-7 ]
  • [ 22819-07-4 ]
  • ethyl isocyano formate [ No CAS ]
  • [ 1431968-95-4 ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 5h;
  • 12
  • ethoxycarbonyl isothiocyanate [ No CAS ]
  • [ 22819-07-4 ]
  • [ 1431968-97-6 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 20℃; for 5h;
  • 13
  • [ 937-39-3 ]
  • [ 22819-07-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / 72 h / 20 °C 2: water / 180 °C / Microwave irradiation
  • 14
  • [ 103-80-0 ]
  • [ 22819-07-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / 0.33 h / 180 °C 2: water / 180 °C / Microwave irradiation
  • 15
  • [ 22819-07-4 ]
  • ethyl isocyano formate [ No CAS ]
  • [ 1431968-95-4 ]
YieldReaction ConditionsOperation in experiment
With N,N-dimethyl-formamide at 20℃;
  • 16
  • [ 22819-07-4 ]
  • 2-benzyl-5-(methylthio)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 20 °C 2: sodium hydroxide / ethanol; water / 0.33 h / 100 °C 3: sodium hydroxide / water / 0.5 h / 20 °C
  • 32
  • [ 81581-27-3 ]
  • [ 22819-07-4 ]
  • [ 1607425-60-4 ]
YieldReaction ConditionsOperation in experiment
25% With toluene-4-sulfonic acid; In butan-1-ol;Reflux; To a solution of 3-benzyl-lH-l,2,4-triazol-5-amine (100 mg, 0.57 mmol) in n- BuOH (3 ml) was added ethyl 3-(2H-l,3-benzodioxol-5-yl)-3-oxopropanoate (200 mg, 0.85 mmol) and 4-methylbenzene-l -sulfonic acid (4 mg, 0.02 mmol). After stirring overnight at reflux, the solids were collected by filtration and washed with ethyl acetate (3 x 10 mL), methanol (3 x 10 ml) and dried to give 5- (benzo[if|[l,3]dioxol-5-yl)-2-benzyl-[l,2,4]triazolo[l,5-fl]pyrimidin-7(4H)-one as a white solid (50.2 mg, 25 ). LC/MS (ES, m/z): [M+H]+ 347.05 *H NMR (300 MHz, DMSO) delta 7.43 -7.56 (m, 2H), 7.18 - 7.35 (m, 5H), 7.05 (d, / = 8.1 Hz, 1H), 6.28 (s, 1H), 6.12 (s, 2H), 4.10 (s, 2H)
  • 33
  • [ 74053-94-4 ]
  • [ 22819-07-4 ]
  • [ 1607425-77-3 ]
YieldReaction ConditionsOperation in experiment
8% With acetic acid at 110℃; 18 2-Benzyl-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one A mixture of 5-benzyl-2H-l ,2,4-triazol-3-amine (174 mg, 1.00 mmol, 1.00 equiv), acetic acid (3 mL), and ethyl 3-(2,3-dihydrobenzo[^] [l ,4]dioxin-6-yl)-3- oxopropanoate (275 mg, 1.10 mmol, 1.10 equiv) was stirred overnight at 110°C. The reaction was concentrated to dryness and purified with prep-TLC (MeOH:DCM=l :30) to afford 30.7 mg (8%) of 2-benzyl-5-(2,3- dihydrobenzo[^] [l ,4]dioxin-6-yl)-[l ,2,4]triazolo[l ,5-fl]pyrimidin-7(4H)-one as a yellow solid. LC-MS: (ES, m/z): 361 [M+H]+ *H NMR (300 MHz, DMSO, ppm) 7.44-7.21 (m, 7H), 6.98 (d, /=8.4Hz, 1H), 6.20 (s, 1H), 4.29 (s, 4H), 4.07 (s, 2H)
  • 34
  • [ 22819-07-4 ]
  • [ 2881-83-6 ]
  • [ 1607425-78-4 ]
YieldReaction ConditionsOperation in experiment
8% With acetic acid at 110℃; 19 2-Benzyl-5-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one A mixture of 5-benzyl-2H-l ,2,4-triazol-3-amine (174 mg, 1.00 mmol, 1.00 equiv), acetic acid (3 mL), and ethyl 3-(4-methoxyphenyl)-3-oxopropanoate (228 mg, 1.10 mmol, 1.10 equiv) was stirred overnight at 1 10°C and then concentrated to dryness. The resulting solid was washed with 5 mL MeOH and collected by filtration. The solid was dissolved in 10 mL of NH4OH (aq.) and filtered. The filtrate was adjusted to pH 6 with HO Ac. The resulting solid was collected by filtration and washed with water. The solid was dried to get 26 mg (8%) of 2-benzyl-5-(4-methoxyphenyl)- [l ,2,4]triazolo[l ,5-fl]pyrimidin-7(4H)-one as a white solid. LC-MS: (ES, m/z): 333 [M+H]+ *H NMR (300 MHz, DMSO, ppm) 13.36 (s, 1H), 7.86 (d, /=8.7Hz, 2H), 7.38-7.21 (m, 5H), 7.09 (d, /=9Hz, 2H), 6.26 (s, 1H), 4.10 (s, 2H), 3.83 (s, 3H)
  • 35
  • [ 37779-49-0 ]
  • [ 22819-07-4 ]
  • 2,5-dibenzyl-4H-[1,2,4]triazolo[1,5-a]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With toluene-4-sulfonic acid; In butan-1-ol; at 125℃; for 24h; General procedure: A mixture of compound 3 (5.7 mmol), compound 4 (11.5 mmol)and p-TsOH (1.5 mmol) in n-BuOH (15 mL) was stirred at 125 C for 24 he48 h. After the volatile was evaporated under vacuum, theresidue was purified by flash column using DCM/Methanol 20:1as the eluent to afford the compound 5e8 with yield in the range of 45-85%.
  • 36
  • [ 614-27-7 ]
  • [ 22819-07-4 ]
  • 2-benzyl-5-phenyl-4H-[1,2,4]triazolo[1,5-a]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With toluene-4-sulfonic acid In butan-1-ol at 125℃; for 24h; 4.1.3. Synthesis of [1,2,4]triazolo[1,5-a]pyrimidin -7-one derivatives(5e8) [5] General procedure: A mixture of compound 3 (5.7 mmol), compound 4 (11.5 mmol)and p-TsOH (1.5 mmol) in n-BuOH (15 mL) was stirred at 125 C for 24 he48 h. After the volatile was evaporated under vacuum, theresidue was purified by flash column using DCM/Methanol 20:1as the eluent to afford the compound 5e8 with yield in the range of 45-85%.
  • 37
  • [ 18698-96-9 ]
  • [ 22819-07-4 ]
  • C17H15IN4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethylsulfoxide-d6 at 20℃; for 3h;
  • 38
  • [ 85977-52-2 ]
  • [ 22819-07-4 ]
  • C20H20N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethylsulfoxide-d6 at 20℃; for 3h;
  • 39
  • [ 1937-19-5 ]
  • [ 103-80-0 ]
  • [ 22819-07-4 ]
YieldReaction ConditionsOperation in experiment
31% Stage #1: 1-aminoguanidine hydrochloride; phenylacetyl chloride With potassium hydroxide In tetrahydrofuran; water at 0℃; for 1h; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water Reflux;
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