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[ CAS No. 22819-05-2 ]

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Chemical Structure| 22819-05-2
Chemical Structure| 22819-05-2
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Product Details of [ 22819-05-2 ]

CAS No. :22819-05-2 MDL No. :MFCD03085910
Formula : C4H8N4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZVWFWIXWMIMWEU-UHFFFAOYSA-N
M.W :112.13 g/mol Pubchem ID :1714204
Synonyms :

Calculated chemistry of [ 22819-05-2 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 30.56
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) : -6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.81
Log Po/w (XLOGP3) : 0.47
Log Po/w (WLOGP) : -0.04
Log Po/w (MLOGP) : -0.31
Log Po/w (SILICOS-IT) : 0.61
Consensus Log Po/w : 0.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.23
Solubility : 6.64 mg/ml ; 0.0592 mol/l
Class : Very soluble
Log S (Ali) : -1.46
Solubility : 3.9 mg/ml ; 0.0348 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.24
Solubility : 6.51 mg/ml ; 0.0581 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.13

Safety of [ 22819-05-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 22819-05-2 ]

* 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 [ 22819-05-2 ]

[ 22819-05-2 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 10308-82-4 ]
  • [ 802294-64-0 ]
  • [ 22819-05-2 ]
YieldReaction ConditionsOperation in experiment
With water
  • 2
  • [ 22819-05-2 ]
  • [ 141-97-9 ]
  • [ 90953-10-9 ]
YieldReaction ConditionsOperation in experiment
2.4 g In acetic acid for 6h; Heating;
YieldReaction ConditionsOperation in experiment
51.95 g (65%) 3 Preparation of 3-Amino-5-ethyl-1,2,4-triazole EXAMPLE 3 Preparation of 3-Amino-5-ethyl-1,2,4-triazole To a cooled solution (0°-5° C.) of 89.4g (0.71 mole) of ethyl N-cyanoimidate (from Example 2), in approximately 400 ml of methanol, was added dropwise, with stirring under nitrogen atmosphere, 23.6 g (0.736 mole) of anhydrous hydrazine. When addition was complete (about 15 minutes), the mixture was stirred for approximately 20 minutes in an ice bath, during which time the solution began to turn pink. The solution was then stirred approximately 30 minutes at about 20° C. Concentration in vacuo provided a white solid which was immediately recrystallized from about 1.1 liters of acetonitrile, followed by filtering, washing with ethyl acetate to remove any residual pink color and drying in a vacuum oven to give 51.95 g (65%) of pink needles of 3-amino-5-ethyl-1,2,4-triazole, m.p. 150°-152° C. [lit. (J. Chem. Soc., 1929, 815) m.p. 152° C.]. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.
  • 4
  • [ 22819-05-2 ]
  • [ 55314-16-4 ]
  • 2-Ethyl-7-(pyridin-3-yl)[1,2,4]triazolo[1,5-a]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetic acid; EXAMPLE 7 2-Ethyl-7-(3-pyridyl)[1,2,4]triazolo[1,5-a]pyrimidine A mixture of 1.12 g of 3-amino-5-ethyl-1,2,4-triazole and 1.76 g of 3-dimethylamino-1-(3-pyridyl)-2-propene-1-one in 25 ml of glacial acetic acid was refluxed for six hours and the procedure of Example 1 was continued to give 1.51 g of the desired product as colorless needles, mp 147-149 C. The following additional Examples for the preparation of 2-ethyl-7-(heteroaryl and substituted heteroaryl)[1,2,4]triazolo[1,5-a]pyrimidines listed in Table II were prepared by the procedure described in Example 7.
  • 5
  • [ 22819-05-2 ]
  • 3-(1-pyrrolidinyl)-1-(thien-2-yl)-2-buten-1-one [ No CAS ]
  • 2-ethyl-5-methyl-7-(thien-2-yl)[1,2,4]triazolo[1,5-a]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetic acid 13 2-Ethyl-5-methyl-7-(2-thienyl)[1,2,4,]triazolo[1,5-a]pyrimidine EXAMPLE 13 2-Ethyl-5-methyl-7-(2-thienyl)[1,2,4,]triazolo[1,5-a]pyrimidine A reaction mixture of 2.21 g of 3-amino-5-ethyl-1,2,4-triazole and 2.21 g of 3-(1-pyrrolidinyl)-1-(2-thienyl)-2-buten-1-one in 25 ml of glacial acetic acid was refluxed for 6 hours. The resulting mixture was worked up as described in Example 11 to give 1.93 g of the desired product as tan crystals, mp 103°-104° C.
  • 6
  • [ 22819-05-2 ]
  • [ 72851-19-5 ]
  • 2-Ethyl-7-(m-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetic acid 57 2-Ethyl-7-(m-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine EXAMPLE 57 2-Ethyl-7-(m-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine A mixture of 2.24 g. of 3-amino-5-ethyl-1,2,4-triazole and 4.86 g. of 3-dimethylamino-3'-trifluoromethylacrylophenone in 50 ml. of glacial acetic acid is refluxed for 16 hours. The resulting mixture is worked up as described in Example 54 to give the product of the Example, m.p. 132°-134° C.
  • 7
  • [ 22819-05-2 ]
  • [ 83-13-6 ]
  • [ 1116117-28-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-amino-5-ethyl-1H-1,2,4-triazole; diethyl 2-phenylmalonate With tributyl-amine at 185℃; Stage #2: With sodium hydroxide; water for 0.5h; Stage #3: With hydrogenchloride In water 40.1 A solution of 5.0Og 3-amino-5-ethyl-1 ,2,4-triazole and 15.0Og diethyl phenylmalonate in 18ml N,N-dibutylbutan-1-amine is stirred at 185°C over night. The solution is diluted with 5N NaOH solution, the resulting mixture is stirred for 30min. The aqueous layer is washed with diethylether, acidified at 00C with concentrated HCI until precipition of the product is complete. The precipitate is collected by filtration to yield the product, which is used without further purification. MS (IVM ): 257Characteristic 1 H NMR (300MHz, dDMSO) signals: 7.4ppm (m, 2H); 7.3ppm (m, 2H); 7.1 ppm (m, 1 H); 2.8ppm (q, 2H); 1.3ppm (t, 3H)
With tributyl-amine at 185℃; 40.1 A solution of 5.00 g 3-amino-5-ethyl-1,2,4-triazole and 15.00 g diethyl phenylmalonate in 18 ml N,N-dibutylbutan-1-amine is stirred at 185° C. over night. The solution is diluted with 5N NaOH solution, the resulting mixture is stirred for 30 min. The aqueous layer is washed with diethylether, acidified at 0° C. with concentrated HCl until precipition of the product is complete. The precipitate is collected by filtration to yield the product, which is used without further purification.MS (M+1): 257Characteristic 1H NMR (300 MHz, dDMSO) signals: 7.4 ppm (m, 2H); 7.3 ppm (m, 2H); 7.1 ppm (m, 1H); 2.8 ppm (q, 2H); 1.3 ppm (t, 3H)
Stage #1: 3-amino-5-ethyl-1H-1,2,4-triazole; diethyl 2-phenylmalonate With tributyl-amine In N,N-dimethyl-formamide at 185℃; Stage #2: With sodium hydroxide In water for 0.5h; Stage #3: With hydrogenchloride In water at 0℃; 30.0.1 Intermediate Example 30.0: 4-(2-Ethyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin- 5-yl)benzaldehyde; Stepi : 2-Ethyl-6-phenyl[1 ,2,4]triazolo[1 ,5-a]pyrimidine-5,7-diol; A solution of 5.0Og 3-amino-5-ethyl-1 ,2,4-triazole and 15.0Og diethyl phenylmalonate in 18ml_ N,N-dibutylbutan-1-amine was stirred at 185°C over night. The solution was diluted with 5N NaOH solution, the resulting mixture was stirred for 30min. The aqueous layer was washed with diethylether, acidified at 00C with concentrated HCI until precipition of the product was complete. The precipitate was collected by filtration to yield the product, which was used without further purification. MS (M+1): 257 Characteristic 1 H NMR (300MHz, d6-DMSO) signals: 7.4ppm (m, 2H); 7.3ppm (m, 2H); 7.1ppm (m, 1 H); 2.8ppm (q, 2H); 1.3ppm (t, 3H)
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