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Chemical Structure| 452-58-4 Chemical Structure| 452-58-4

Structure of 452-58-4

Chemical Structure| 452-58-4

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Product Details of [ 452-58-4 ]

CAS No. :452-58-4
Formula : C5H7N3
M.W : 109.13
SMILES Code : C1=C(C(=NC=C1)N)N
MDL No. :MFCD00006319
InChI Key :ZZYXNRREDYWPLN-UHFFFAOYSA-N
Pubchem ID :9956

Safety of [ 452-58-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501

Application In Synthesis of [ 452-58-4 ]

* 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 [ 452-58-4 ]

[ 452-58-4 ] Synthesis Path-Downstream   1~19

  • 2
  • [ 452-58-4 ]
  • [ 517-21-5 ]
  • [ 322-46-3 ]
  • 3
  • [ 5409-39-2 ]
  • [ 452-58-4 ]
  • 4
  • [ 4845-50-5 ]
  • [ 452-58-4 ]
  • [ 322-46-3 ]
  • 6
  • [ 452-58-4 ]
  • 3-morpholino-1-ethyl-1,2,4-triazinium borofluoride [ No CAS ]
  • [ 322-46-3 ]
  • 8
  • [ 452-58-4 ]
  • [ 3973-08-8 ]
  • [ 1848-82-4 ]
  • 9
  • [ 452-58-4 ]
  • [ 68175-07-5 ]
  • 10
  • [ 452-58-4 ]
  • [ 56291-51-1 ]
  • 11
  • [ 452-58-4 ]
  • [ 64-19-7 ]
  • [ 68175-07-5 ]
YieldReaction ConditionsOperation in experiment
55.0% A solution of pyridinediamine (IX), (X), (45.8 mmoles), acetic acid (458.0 mmoles) in PPA (50 ml) was heated to 135-14O0C for 2-4 h under nitrogen atmosphere. After completion of reaction, cooled, transferred the reaction to 250 ml of cold water, charcoal was added and the mixture filtered over a celite bed. The filtrate was basified with aq. ammonia solution till the pH~10-12. Extracted the basified reaction with ethyl acetate (250 ml X3), dried the ethyl acetate layer with sodium sulfate and distilled off the solvent completely to residue. To the residue hexane (50 ml) was added and filtered to get the desired compound (XI and XII). Table 6 : Imdiazopyridines (XI), (XII):
  • 12
  • [ 452-58-4 ]
  • [ 27143-07-3 ]
  • [ 1144161-09-0 ]
  • 14
  • [ 452-58-4 ]
  • [ 623-51-8 ]
  • [ 68175-07-5 ]
  • 15
  • [ 452-58-4 ]
  • [ 582-80-9 ]
  • N-(4-(3H-imidazo[4,5-b]pyridin-2-yl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 19h; c) N-(4-(3H-lmidazo[4,5-b]pyridin-2-yl)phenyl)benzamide (3) 4-Benzamidobenzoic acid A13 (0.10 g, 0.42 mmol), HOBt (0.067 g, 0.50 mmol), EDCI (0.095 g, 0.50 mmol), pyridine-2,3-diamine A5 (0.047 g, 0.46 mmol), DMF (2 mL) and DIPEA (0.17 mL, 1.0 mmol) were stirred together at room temperature for 19 hours. The solution was added to water (15 mL), stood for twenty minutes and filtered. The collected solid was dissolved in glacial acetic acid (3.0 mL) and heated in the microwave twice (140 °C for 1 hour, then 140 °C for 30 minutes). The cooled mixture was concentrated in vacuo, the residue partitioned between EtOAc (50 mL) and 1 M pH 7 potassium phosphate buffer (50 mL). The aqueous phase was extracted with EtOAc (2 chi 25 mL), and the combined EtOAc extracts dried (MgS04) and concentrated in vacuo. The product was purified twice by silica gel chromatography (12 g silica cartridge, 50-100percent EtOAc in petroleum benzine 40-60 °C, then 12 g silica cartridge, 60-70percent EtOAc in petroleum benzine 40-60 °C) to give the title compound (0.025 g, 19percent) as a white solid. H NMR (400 MHz, cf DMSO) delta 13.35 (br s, 1 H) 10.51 (s, 1 H), 8.31 (d, J = 3.9 Hz, 1 H), 8.22 (d, J = 8.8 Hz, 2H), 8.04 - 7.93 (m, 4H), 7.65 - 7.60 (m, 1 H), 7.60 - 7.53 (m, 2H), 7.22 (dd, J = 7.9, 4.8 Hz, 1 H). One NH proton not observed. LCMS-A rt 4.40 min, m/z (positive ion) 315.2 [M+H]+, m/z (negative ion) 313.1 [M- H]-.
  • 16
  • [ 452-58-4 ]
  • [ 2142-04-3 ]
  • 2-(3H-imidazo[4,5-b]pyridine-2-yl)-N-(4-methoxyphenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; at 100℃;Green chemistry; General procedure: A mixture of 5a-5l (10 mmol), 3 (10 mmol) in water (20mL) was refluxed for 60-90 min. At the end of this period, a colourless solid separated out from the reaction mixture which was collected by filtration. The isolated solid was washed with water (10 mL) and dried. The crude product was recrystallized from a suitable solvent to obtain 4a-4l.
  • 17
  • [ 452-58-4 ]
  • [ 141-97-9 ]
  • [ 68175-07-5 ]
YieldReaction ConditionsOperation in experiment
86% With gadolinium(III) chloride hexahydrate; at 80℃; for 5h; General procedure: To a mixture of o-aromatic diamines (200 mg, 1.85 mmol) and 1,3-dicarbonyl compound (722 mg, 5.55 mmol), GdCl3*6H2O (25 mg, 0.09 mmol) was added and the mixture was stirred at 80°C for 3.0 hr. After completion of the reaction (TLC), the reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the corresponding 2-methyl benzimidazole. The crude material was further purified by through column chromatography by using 10percent ethyl acetate in hexane.
  • 18
  • [ 452-58-4 ]
  • [ 72551-53-2 ]
  • C18H20N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With polyphosphoric acid; at 180℃; for 16h; A mixture of 2,3-pyridinediamine (321 mg, 2.95 mmol), ethyl l-benzyl-3- piperidinecarboxylate (CAS: 72551-53-2; 850 mg, 2.98 mmol) and polyphosphoric acid (5 mL) was stirred at 180 C for 16 h. Then the mixture was cooled to rt. Water was added and the mixture was stirred at 50 C until it became homogeneous. This mixture was then cooled to room temperature and aqueous NaOH (3N) was added until pH = 8 was reached. Then EtOAc was added and the organic layer was separated, dried over Na2S04, filtered and the filtrate was evaporated in vacuo. The resultant oil was purified by flash column chromatography (silica; 7M solution of ammonia in MeOH in EtOAc 0/100 to 10/90). The desired fractions were concentrated in vacuo to yield intermediate 29 as yellow oil (430 mg, 50% yield).
  • 19
  • [ 452-58-4 ]
  • [ 87220-68-6 ]
  • C24H16N4 [ No CAS ]
  • C24H16N4 [ No CAS ]
 

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Technical Information

Categories

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