Structure of 452-58-4
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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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 |
GHS Pictogram: |
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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 |
* 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.
Yield | Reaction Conditions | Operation 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): |
Yield | Reaction Conditions | Operation 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]-. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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). |
A147587 [24188-40-7]
N2-Isopropylpyridine-2,3-diamine
Similarity: 0.78
A147587 [24188-40-7]
N2-Isopropylpyridine-2,3-diamine
Similarity: 0.78