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[ CAS No. 58481-04-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 58481-04-2
Chemical Structure| 58481-04-2
Chemical Structure| 58481-04-2
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Product Details of [ 58481-04-2 ]

CAS No. :58481-04-2 MDL No. :MFCD00221428
Formula : C6H6ClN3O Boiling Point : -
Linear Structure Formula :- InChI Key :MZIIYNBBSHJOLD-UHFFFAOYSA-N
M.W : 171.58 Pubchem ID :236206
Synonyms :

Calculated chemistry of [ 58481-04-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.14
TPSA : 68.01 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) : -7.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.95
Log Po/w (XLOGP3) : 0.11
Log Po/w (WLOGP) : 0.34
Log Po/w (MLOGP) : 0.15
Log Po/w (SILICOS-IT) : 0.38
Consensus Log Po/w : 0.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.24
Solubility : 9.77 mg/ml ; 0.0569 mol/l
Class : Very soluble
Log S (Ali) : -1.09
Solubility : 13.8 mg/ml ; 0.0806 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.28
Solubility : 0.907 mg/ml ; 0.00528 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 58481-04-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 58481-04-2 ]

* 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 [ 58481-04-2 ]

[ 58481-04-2 ] Synthesis Path-Downstream   1~60

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  • 22
  • [ 58481-04-2 ]
  • [4-(5-Amino-1H-[1,2,4]triazol-3-yl)-pyridin-2-yl]-(4-tert-butyl-benzyl)-amine [ No CAS ]
  • 23
  • [ 6313-54-8 ]
  • [ 58481-04-2 ]
YieldReaction ConditionsOperation in experiment
57% HOBt (823 mg, 6.09 mmol), and EDCI (1.2 g, 6.09 mmol) were added to a suspension of 2-chloro-isonicotinic acid (800 mg, 5.08 mmol) in acetonitrile (10.3 ml) at room temperature. After two h a solution of hydrazine monohydrate (0.493 ml, 10.2 mmol) in acetonitrile (5.0 ml) was added drop-wise at [0C.] After 30 min, the solvent was removed using a roto-evaporator and the residue was diluted with ethyl acetate, quenched with water, dried over sodium sulfate, filtered and concentrated to afford 2-chloro-isonicotinic acid hydrazide (493 mg, 57%, yellow solid). 1H NMR (DMSO) d (ppm): 10.21 (bs, [1H),] 8.55 (d, 1H), 7.82 (s, 1H), 7.75 (d, 1H), 4.69 (bs, 2H).
  • 24
  • [ 58481-04-2 ]
  • [ 159634-59-0 ]
  • C24H27ClN4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With sulfuric acid; In ethanol; for 5h;Heating / reflux; Step A:; To a solution of spiro [indan-l-one-3, 4'-piperidine]-l'-carboxylic acid tert-butyl ester (1.5 g) and 2-chloro-isonicotinic acid hydrazide (858 mg) in ethanol (50 ml) was added one drop of sulphuric acid, and the mixture was refluxed for 5 hours. The solvent was evaporated then the residue was dissolved in dichloromethane, the organic layer washed with saturated aqueous sodium bicarbonate, dried (sodium sulphate) and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent ethyl acetate: cyclohexane 6: 4) to give 1.6 g (70%) of the hydrazide LXVIII. 2 as a yellowish solid; M. p. 90-95C. MS (ES+) 455 (M+H+), 399 (M-isobutene+H).
  • 25
  • [ 855849-88-6 ]
  • [ 58481-04-2 ]
  • 2-chloroisonicotinic acid [1'-[trans-3-(4-chlorophenyl)allyl]spiro[indan-1-ylidene-3,4'-piperidine]]hydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In ethanol; for 12h;Heating / reflux; EXAMPLE 3; This Example illustrates the preparation of compound ni. 3,2-chloroisonicotinic acid [1'- [trans-3- (4-chlorophenyl) allyl] spiro [indan-1-ylidene-3, 4'-piperidine]] hydrazide; To a solution of l'- [trayzs-3- (4-chlorophenyl) allyl] spiro [indan-1-one-3, 4'-piperidine] (example 1, step B) (20 mg) in ethanol (3 ml) was added <strong>[58481-04-2]2-chloro-isonicotinic acid hydrazide</strong> (15 mg) and one drop of sulphuric acid. The reaction mixture was refluxed for 12 hours and concentrated in vacuo. The residue was dissolved in dichloromethane, washed with saturated aqueous sodium bicarbonate, dried (sodium sulphate) and concentrated in vacuo. The solid residue was purified by preparative HPLC to give 22 mg of 2- chloroisonicotinic acid [1'- [trans-3- (4-chlorophenyl) allyl] spiro [indan-1-ylidene-3, 4'- piperidine] ] hydrazide; M. p. 240C. IH NMR (400 MHz, CDCl3) 1.5 (m, 2H), 2.15 (m, 4H), 2.70 (s, 2H), 3.03 (m, 2H), 3.21 (m, 2H), 6.26 (dt, J = 15.8 Hz, 5.8 Hz, 1H), 6.45 (d, J = 15.8Hz, 1H), 7.1-7. 9 (m, 10H) ; 8.50 (d, J = 4.7 Hz, 1H), 9.42 (br s, 1H) ; MS (ES+) 505/507 (M+H+).
  • 26
  • [ 58481-04-2 ]
  • C12H16N2O4 [ No CAS ]
  • C17H18ClN5O4 [ No CAS ]
  • 27
  • [ 100-48-1 ]
  • [ 58481-04-2 ]
  • C12H10ClN5O [ No CAS ]
  • 28
  • [ 14906-59-3 ]
  • [ 58481-04-2 ]
  • [ 837371-87-6 ]
YieldReaction ConditionsOperation in experiment
Reference Example 3 Preparation of 5-(1-oxy-4-pyridyl)-3-(2-chloro-4-pyridyl)-1,2,4-triazole To a suspension of 4-cyanopyridine-N-oxide (5.00 g) in methanol (40.0 mL) was added sodium methoxide (0.22 g) in an argon atmosphere, and the mixture was stirred at room temperature for 2 hours. Then <strong>[58481-04-2]2-chloro-isonicotinic acid hydrazide</strong> (7.14 g) was added thereto, and the resulting mixture was refluxed for 1.5 hours and DMF (35.0 mL) was added thereto. After distilling away methanol, the resulting mixture was heated to 120C for 24 hours. After heating, the reaction mixture was cooled to room temperature. Precipitated white crystals were filtered, washed successively with DMF and methanol, and dried under reduced pressure to give 9.50 g of the captioned compound as white crystals. 1H NMR(DMSO-d6) delta(ppm): 7.99-8.04 (m, 4H), 8.38 (d, 2H, J=1.35Hz), 8.59 (d, 1H, J=4.86Hz)
  • 29
  • [ 58481-04-2 ]
  • [ 2740-81-0 ]
  • [ 350249-18-2 ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 18h; A mixture of l-chloro-2-isothiocyanatobenzene 1 (0.4 g, 2.33 mmol) and 2-chloropyridine-4- carbohydrazide 11 (0.4 g, 2.33 mmol) in DMF was stirred at ambient temperature for 18 hours, concentrated to dryness, and 20 mL of 10% K2CO3(aq.) was added. The resulting mixture was stirred under reflux for 6 hours. The clear solution was cooled to ambient temperature, washed with ether, and acidified with IN HCl. The solid was collected, washed with H2O and ether, and dried to afford compound 13 (4.3 g). Yield: 86%.1H-NMR (300 MHz, CHLOROFORM-d) delta (ppm): 8.30 (d, 1 H), 7.63-7.18 (m, 5 H), 7.16 (d, IH).
  • 30
  • [ 75-15-0 ]
  • [ 58481-04-2 ]
  • [ 1357083-08-9 ]
YieldReaction ConditionsOperation in experiment
General procedure: Then equimolar portions of the appropriately substituted benzoylhydrazine (5 mmol) and potassium hydroxide (5 mmol) were dissolved in 20 mL of 95% ethanol. The mixture was allowed to stir for several minutes at room temperature and then carbon disulfide (7.5 mmol) was slowly added dropwise to the reaction system via a self-equalizing addition funnel while the mixture was heated to reflux. After 24 h, the solvent was completely removed under reduced pressure. The residue obtained was dissolved in water (50 mL) and diluted hydrochloric acid was added to adjust the pH values of the solution to 5-6. Then the precipitate was collected by filtering under reduced pressure, washed with water for several times and dried without further purification.
  • 31
  • [ 58481-04-2 ]
  • [ 1357083-16-9 ]
  • 32
  • [ 54453-93-9 ]
  • [ 58481-04-2 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate; In ethanol; for 5h;Reflux; General procedure: For the synthesis of substituted benzoylhydrazines, a mixture of corresponding esters (20 mmol), 85% hydrazine hydrate (20 mmol) in ethanol (35 ml) was heated to reflux for 5 h. After that, the solution was poured into ice-water. The precipitate was filtered and crystallized from ethanol.
  • 33
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  • [ 1380395-59-4 ]
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  • [ 1380395-65-2 ]
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  • [ 58481-04-2 ]
  • [ 1429183-52-7 ]
  • 36
  • [ 58481-04-2 ]
  • 3-(4-chlorophenyl)-4,6-dimethoxy-7-trichloroacetyl-1H-indole [ No CAS ]
  • N'-(2-chloroisonicotinoyl)-3-(4-chlorophenyl)-4,6-dimethoxy-1H-indole-7-carbohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine; In acetonitrile; for 24h;Reflux; General procedure: A mixture of 7-trichloroacetylindole 5a or 5b (0.069-0.092 mmol), pyridine-4-carbohydrazide 10a, 10b, 10c or 10d(0.093-0.12 mmol) and triethylamine (5 drops) in anhydrous acetonitrile(10 mL) was heated under reflux for 24 h. After cooling toroom temperature the solvent was evaporated under reduced pressureand the residue recrystallized from anhydrous ethanol to giveN,N0-diacylated hydrazine 11a-h as an off-white, yellow, orangebrownor pale brown solid in 61-88% yield
  • 37
  • [ 58481-04-2 ]
  • [ 1312002-42-8 ]
  • 3-(4-bromophenyl)-N'-(2-chloroisonicotinoyl)-4,6-dimethoxy-1H-indole-7-carbohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With triethylamine; In acetonitrile; for 24h;Reflux; General procedure: A mixture of 7-trichloroacetylindole 5a or 5b (0.069-0.092 mmol), pyridine-4-carbohydrazide 10a, 10b, 10c or 10d(0.093-0.12 mmol) and triethylamine (5 drops) in anhydrous acetonitrile(10 mL) was heated under reflux for 24 h. After cooling toroom temperature the solvent was evaporated under reduced pressureand the residue recrystallized from anhydrous ethanol to giveN,N0-diacylated hydrazine 11a-h as an off-white, yellow, orangebrownor pale brown solid in 61-88% yield
  • 38
  • [ 98-03-3 ]
  • [ 58481-04-2 ]
  • 2-chloro-N'-(thiophen-2-ylmethylene)isonicotinohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% In ethanol; for 24h;Reflux; General procedure: A mixture of pyrrole-, furan- or thiophene-2-carbaldehyde12a-c (0.21-0.27 mmol) and pyridine-4-carbohydrazide 10a, 10bor 10c (0.19-0.23 mmol) in anhydrous ethanol (10 mL) was heatedunder reflux for 24 h. After cooling to room temperature the solventwas evaporated under reduced pressure and the residuerecrystallized from anhydrous ethanol (14c-g) or ethyl acetate(14a-b) to give imine-carbohydrazide 14a-g as a white, off-white,pale brown or green-brown solid in 52-70% yield.
  • 39
  • [ 1003-29-8 ]
  • [ 58481-04-2 ]
  • N'-((1H-pyrrol-2-yl)methylene)-2-chloroisonicotinohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% In ethanol; for 24h;Reflux; General procedure: A mixture of pyrrole-, furan- or thiophene-2-carbaldehyde12a-c (0.21-0.27 mmol) and pyridine-4-carbohydrazide 10a, 10bor 10c (0.19-0.23 mmol) in anhydrous ethanol (10 mL) was heatedunder reflux for 24 h. After cooling to room temperature the solventwas evaporated under reduced pressure and the residuerecrystallized from anhydrous ethanol (14c-g) or ethyl acetate(14a-b) to give imine-carbohydrazide 14a-g as a white, off-white,pale brown or green-brown solid in 52-70% yield.
  • 40
  • [ 98-01-1 ]
  • [ 58481-04-2 ]
  • 2-chloro-N'-(furan-2-ylmethylene)isonicotinohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% In ethanol; for 24h;Reflux; General procedure: A mixture of pyrrole-, furan- or thiophene-2-carbaldehyde12a-c (0.21-0.27 mmol) and pyridine-4-carbohydrazide 10a, 10bor 10c (0.19-0.23 mmol) in anhydrous ethanol (10 mL) was heatedunder reflux for 24 h. After cooling to room temperature the solventwas evaporated under reduced pressure and the residuerecrystallized from anhydrous ethanol (14c-g) or ethyl acetate(14a-b) to give imine-carbohydrazide 14a-g as a white, off-white,pale brown or green-brown solid in 52-70% yield
  • 41
  • [ 58481-04-2 ]
  • C24H21F2N7O [ No CAS ]
  • 42
  • [ 58481-04-2 ]
  • C30H25F2N7O [ No CAS ]
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  • [ 58481-04-2 ]
  • C31H27F2N7O [ No CAS ]
  • 44
  • [ 58481-04-2 ]
  • C32H29F2N7O [ No CAS ]
  • 45
  • [ 58481-04-2 ]
  • 4-methyl-5-(2-(methylamino)pyridin-4-yl)-4H-1,2,4-triazole-3-carbaldehyde [ No CAS ]
  • 46
  • [ 58481-04-2 ]
  • 5-(2-(benzylamino)pyridin-4-yl)-4-methyl-4H-1,2,4-triazole-3-carbaldehyde [ No CAS ]
  • 47
  • [ 58481-04-2 ]
  • 4-methyl-5-(2-((2-phenylethyl)amino)pyridin-4-yl)-4H-1,2,4-triazole-3-carbaldehyde [ No CAS ]
  • 48
  • [ 58481-04-2 ]
  • 4-methyl-5-(2-((3-phenylpropyl)amino)pyridin-4-yl)-4H-1,2,4-triazole-3-carbaldehyde [ No CAS ]
  • 49
  • [ 58481-04-2 ]
  • (4-methyl-5-(2-(methylamino)pyridin-4-yl)-4H-1,2,4-triazol-3-yl)methanol [ No CAS ]
  • 50
  • [ 58481-04-2 ]
  • (5-(2-(benzylamino)pyridin-4-yl)-4-methyl-4H-1,2,4-triazol-3-yl)methanol [ No CAS ]
  • 51
  • [ 58481-04-2 ]
  • (4-methyl-5-(2-((2-phenylethyl)amino)pyridin-4-yl)-4H-1,2,4-triazol-3-yl)methanol [ No CAS ]
  • 52
  • [ 58481-04-2 ]
  • (4-methyl-5-(2-((3-phenylpropyl)amino)pyridin-4-yl)-4H-1,2,4-triazol-3-yl)methanol [ No CAS ]
  • 53
  • [ 58481-04-2 ]
  • (5-(2-chloropyridin-4-yl)-4-methyl-4H-1,2,4-triazol-3-yl)methanol [ No CAS ]
  • 54
  • [ 58481-04-2 ]
  • N-(2,6-difluorobenzyl)-3-(((4-methyl-5-(2-(methylamino)pyridin-4-yl)-4H-1,2,4-triazol-3-yl)methyl)amino)benzamide [ No CAS ]
  • 55
  • [ 58481-04-2 ]
  • 3-(((5-(2-(benzylamino)pyridin-4-yl)-4-methyl-4H-1,2,4-triazol-3-yl)methyl)amino)-N-(2,6-difluorobenzyl)benzamide [ No CAS ]
  • 56
  • [ 58481-04-2 ]
  • N-(2,6-difluorobenzyl)-3-(((4-methyl-5-(2-((2-phenylethyl)amino)pyridin-4-yl)-4H-1,2,4-triazol-3-yl)methyl)amino)benzamide [ No CAS ]
  • 57
  • [ 58481-04-2 ]
  • N-(2,6-difluorobenzyl)-3-(((4-methyl-5-(2-((3-phenylpropyl)amino)pyridin-4-yl)-4H-1,2,4-triazol-3-yl)methyl)amino)benzamide [ No CAS ]
  • 58
  • [ 58481-04-2 ]
  • C7H13NO2S [ No CAS ]
  • ethyl 5-(2-chloropyridin-4-yl)-4-methyl-4H-1,2,4-triazole-3-carboxylate [ No CAS ]
  • 59
  • [ 58481-04-2 ]
  • [ 3376-24-7 ]
  • C17H17ClN2O2 [ No CAS ]
  • 60
  • [ 58481-04-2 ]
  • C6H3ClNO [ No CAS ]
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