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Chemical Structure| 4887-81-4 Chemical Structure| 4887-81-4

Structure of 4887-81-4

Chemical Structure| 4887-81-4

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Product Details of [ 4887-81-4 ]

CAS No. :4887-81-4
Formula : C9H10N2O
M.W : 162.19
SMILES Code : CC1=NC2=CC(OC)=CC=C2N1
MDL No. :MFCD00767455

Safety of [ 4887-81-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P264-P302+P352-P304+P340-P305+P351+P338-P332+P313-P337+P313

Application In Synthesis of [ 4887-81-4 ]

* 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 [ 4887-81-4 ]

[ 4887-81-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 593-75-9 ]
  • [ 42182-27-4 ]
  • [ 4887-81-4 ]
  • [ 74-88-4 ]
  • 2-(6-methoxy-1-methyl-1H-1,3-benzodiazol-2-yl)-3-(methylamino)imidazo[1,2-a]pyridine-7-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% 5-Methoxy-2-methyl-lH-l,3-benzodiazole (500 mg, 3.08 mmol) was dissolved in anhydrous N,N-dimethylformamide (10 mL) and cooled to 0 °C. The solution was treated with sodium hydride (60percent in mineral oil, 185 mg, 4.62 mmol) and stirred at 0 °C for 20 minutes. Methyl iodide (191 mu,, 3.08 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was quenched by the addition of water (10 mL) and extracted with ethyl acetate (2 x 15 mL). Combined organic extracts were washed with water (2 x 10 mL) and brine (2 x 10 mL), dried, filtered and concentrated. Purification by FCC (silica, 12-100percent ethyl acetate in heptane then 10percent methanol in dichloromethane) gave a 1 : 1 mixture of the title compounds 212 mg (40percent yield) as a brown powder. 5H NMR (500 MHz, chloroform) 7.55 (d, J = 8.72 Hz, 1H), 7.19 (d, J = 2.33 Hz, 1H), 7.15 (d, J = 8.73 Hz, 1H), 6.89 (dd, J = 2.37, 8.73 Hz, 1H), 6.86 (dd, J = 2.39, 8.72 Hz, 1H), 6.75 (d, J = 2.33 Hz, 1H), 3.87 (s, 3H), 3.85 (s, 3H), 3.69 (s, 3H), 3.67 (s, 3H), 2.58 (s, 3H), 2.57 (s, 3H). Tr(METCR1278) = 0.77 min, (ES+) (M+H)+ 177 A 1 : 1 mixture of 5-methoxy-l,2-dimethyl-lH-l,3-benzodiazole and 6- methoxy-l,2-dimethyl-lH-l,3-benzodiazole (212 mg, 1.20 mmol) and selenium dioxide (167 mg, 1.50 mmol) were suspended in dioxane (10 mL) in a sealed tube and heated to 1 10 °C for 3 hours. The reaction mixture was filtered through celite, eluting with dioxane until the filtrate ran colourless. The filtrate was concentrated to give a 1 : 1 mixture of the title compounds (186 mg, 81percent yield) as a brown powder. 5H NMR (500 MHz, DMSO) 9.98 (s, 1H), 9.92 (s, 1H), 7.74 (d, J = 8.97 Hz, 1H), 7.67 (d, J = 9.02 Hz, 1H), 7.32 (d, J = 2.34 Hz, 1H), 7.24 (d, J = 2.35 Hz, 1H), 7.15 (dd, J = 2.40, 9.02 Hz, 1H), 7.01 (dd, J = 2.41, 8.97 Hz, 1H), 4.08 (s, 6H), 3.88 (s, 3H), 3.83 (s, 3H). Tr(METCR1278) = 1.00 min, (ES+) (M+H3O)+ 209. A 1 : 1 mixture of 5-methoxy-l-methyl-lH-l,3-benzodiazole-2-carbaldehyde and 6-methoxy-l-methyl-lH-l,3-benzodiazole-2-carbaldehyde (186 mg, 0.98 mmol), <strong>[42182-27-4]2-aminoisonicotinonitrile</strong> (116 mg, 0.98 mmol) and scandium triflate (24 mg, 0.05 mmol) were dissolved in trifluoroethanol (3 mL). Methyl isocyanide (44 muEpsilon, 0.98 mmol) was added and the mixture heated to 160 °C under microwave irradiation for 10 minutes. The reaction mixture was quenched with 1 M hydrochloric acid (2 mL) and concentrated. The residual aqueous suspension was neutralised with saturated aqueous sodium bicarbonate (until effervescence ceased) and extracted with ethyl acetate (2 x 10 mL). Combined organic extracts were washed with brine (10 mL), dried, filtered and concentrated. FCC (silica, 12-100percent ethyl acetate in cyclohexane) gave a mixture of two regioisomers. Purification by preparative HPLC (acetonitrile- water-0.1percent formic acid) gave the title compound 16 mg (25percent yield) as an orange powder. 5H MR (500 MHz, DMSO) 8.47 (d, J = 7.23 Hz, 1H), 8.28 (s, 1H), 7.58 (d, J = 8.74 Hz, 1H), 7.18 (d, J = 2.29 Hz, 1H), 7.15 (dd, J = 1.57, 7.21 Hz, 1H), 6.88 (dd, J = 2.37, 8.74 Hz, 1H), 6.74 (d, J = 5.77 Hz, 1H), 4.26 (s, 3H), 3.86 (s, 3H), 2.98 (d, J = 5.79 Hz, 3H). Tr(MET-uHPLC-AB-lOl) = 2.05 min, (ES+) (M+H)+ 333.
 

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