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Amines
Imidazo[1,2-a]pyridine-6-carboxamide
Amines
Amides Other Aromatic Heterocycles

[ CAS No. 103313-38-8 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 103313-38-8
Chemical Structure| 103313-38-8
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SDS Specification
Alternatived Products of [ 103313-38-8 ]

Product Details of [ 103313-38-8 ]

CAS No. :103313-38-8 MDL No. :MFCD13176747
Formula : C8H7N3O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 161.16 Pubchem ID :-
Synonyms :

Safety of [ 103313-38-8 ]

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

Application In Synthesis of [ 103313-38-8 ]

* 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 [ 103313-38-8 ]

[ 103313-38-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 103313-38-8 ]
  • [ 106850-34-4 ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate R.43.4 (43-4) (43-4) 6-Cyanoimidazo[1,2-a]pyridine A mixture of 2.6 g of 6-carbamoylimidazo[1,2-a]pyridine and 30 ml of phosphorus oxychloride is heated under reflux for 16 hours. The excess phosphorus oxychloride is removed under reduced pressure and the residue is poured onto ice. The mixture is neutralized with sodium carbonate and extracted with ethyl acetate. The organic layer is washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is then evaporated off under reduced pressure to give 2.0 g of the above-identified compound as colorless crystals. M.p.: 166°-167° C. Elemental analysis for C8 H5 N3: Calcd. (%): C, 67.13; H, 3.52; N, 29.35. Found (%): C, 67.37; H, 3.62; N, 28.99.
With trichlorophosphate R.4.1 (4-1) (4-1) 6-Cyanoimidazo[1,2-a]pyridine A mixture of 2.6 g of 6-carbamoylimidazo[1,2-a]pyridine and 30 ml of phosphorus oxychloride is heated under reflux for 16 hours. The excess phosphorus oxychloride is removed under reduced pressure and the residue is poured onto ice. The mixture is neutralized with sodium carbonate and extracted with ethyl acetate. The organic layer is washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is then evaporated off under reduced pressure to give 2.0 g of the above-identified compound as colorless crystals. M.p.: 166°-167° C. Elemental analysis for C8 H5 N3: Calcd.(%): C, 67.13; H, 3.52; N, 29.35. Found (%): C, 67.37; H, 3.62; N, 28.99.
Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US4788185, 1988, A
[2]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US4864022, 1989, A
  • 2
  • [ 136117-69-6 ]
  • [ 103313-38-8 ]
YieldReaction ConditionsOperation in experiment
40% Stage #1: methyl 6-imidazo<1,2-a>pyridinecarboxylate With lithium hydroxide monohydrate; water In methanol at 20 - 60℃; Stage #2: With ammonium chloride; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In methanol at 20℃; for 2h; 19.19a (19a) Imidazo[1,2-a]pyridine-6-carboxamide (19a) Imidazo[1,2-a]pyridine-6-carboxamide Into methanol / water (3 / 1, 40 mL), methyl imidazo[1,2-a]pyridine-6-carboxylate (1.00 g, 5.68 mmol) was dissolved, to which lithium hydroxide monohydrate (286 mg, 6.82 mmol) was added, followed by stirring at room temperature for 45 minutes, and then at 60°C overnight. The resulting reaction liquid was left to cool, to which ammonium chloride (911 mg, 17.0 mmol) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (3.14 g, 11.4 mmol) were added, followed by stirring at room temperature for two hours. To the reaction liquid, water and dichloromethane were added for extraction, and the resulting aqueous layer was further extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. After filtration, the residue thus obtained was purified by basic silica gel column chromatography (hexane : ethyl acetate = 50 : 50, V/V, dichloromethane : methanol = 90 : 10, V/V) to give the desired title compound (0.37 g, yield 40%). 1H-NMR (DMSO-D6) δ: 7.51 (1H, br s), 7.59 (1H, d, J = 9.2 Hz), 7.64-7.67 (2H, m), 8.05-8.07 (2H, m), 9.12-9.13 (1H, m).
Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - EP2565185, 2013, A1 Location in patent: Paragraph 0181

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