Application of 111-95-5,Some common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, molecular formula is C6H15NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A mixture of 3,6-diaminopyrazine-2,5-dicarboxylic acid (200 mg, 1.01 mmol), bis-2- (methoxyethyl)amine (372 mul_, 335.5 mg, 2.52 mmol), HOBt-H2O (459 mg, 3.00 mmol), and EDC-HCI (575 mg, 3.00 mmol) were stirred together in DMF (20 m._) for 1 h at room temperature. The mixture was concentrated to dryness and the residue was partitioned withEtOAc and water. The layers were separated and the EtOAc solution was washed with saturated NaHCO3 and brine. The solution was dried over anhydrous Na2SO4, filtered and concentrated. Purification by radial flash chromatography (SiO2, 10/1 CHCI3-MeOH) afforded 228.7 mg (53% yield) of Example 1 as an orange foam: 1H NMR (300MHz, CDCI3), delta 4.92 (s, 4 H), 3.76 (apparent t, J = 5.4 Hz, 4 H), 3.70 (apparent t, J = 5.6 Hz, 4 H), 3.64 (apparent t, J = 5.4 Hz, 4 H)1 3.565 (apparent t, J = 5.4 Hz), 3.67 (s, 6 H), 3.28 (s, 6 H). 13C NMR (75 MHz, CDCI3) delta 167.6 (s), 145.6 (s), 131.0 (s), 72.0 (t), 70.8 (t), 59.2 (q), 49.7 (t), 47.1 (t). LCMS (5- 95% gradient acetonitrile in 0.1 % TFA over 10 min), single peak retention time = 3.14 min on 30 mm column, (M+H)+ = 429. UV/vis (100 muM in PBS) lambdaabs = 394 nm. Fluorescence (100 nm) lambdaex = 394 nm.lambdaem = 550 nm.
The synthetic route of 111-95-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MALLINCKRODT INC.; WO2007/149479; (2007); A1;,
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