Novel minor groove binders
A compound, methyl technology, applied in the field of synthetic compounds, can solve problems such as no display instructions
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Embodiment 1
[0694] 4-({[4-({4-[(E)-2-(3-methoxyphenyl)vinyl]benzoyl}amino)-1-methyl-1H-pyrrol-2-yl]carboxyl }amino)-1-methyl-N-[2-(4-morpholinyl)ethyl]-1H-pyrrole-2-amide, trifluoroacetate
[0695] To 4-amino-1-methyl-N-[1-methyl-5-({[2-(4-morpholinyl)ethyl]amino}carbonyl)-1H-pyrrole dissolved in DMF (1mL) -3-yl]-1H-pyrrole-2-amide (46 mg, 0.124 mmol; see Preparation 1 above) was added with stirring at room temperature HBTU (100 mg, 0.264 mmol), 4-[(E)-2-(3-methoxybenzene yl)vinyl]benzoic acid (32 mg, 0.124 mmol; see Preparation 4 above). The reaction mixture was left at room temperature overnight. The product was purified by HPLC (without work-up) to afford the title compound (26 mg, 29%) as a pale yellow solid with no apparent melting point.
[0696] 1 H NMR (DMSO-d 6 ): 10.32 (1H, s), 9.97 (1H, s), 9.68 (1H, br), 8.23 (1H, t, 5.6Hz), 7.97 (2H, d, 8.4Hz), 7.75 (2H, d, J =5.6Hz), 7.3-7.29(4H, m), 7.22(2H, m), 7.12(1H, d, J=1.5Hz), 7.00(1H, d, J=1.5Hz), 6.90(1H, dd , J=1.5Hz & J...
Embodiment 2
[0700] 1-methyl-4-({[1-methyl-4-{4-[(E)-2-(3-quinoline)vinyl]benzoyl}amino)-1H-pyrrole-2-] Carbonyl}amino)-N-[2-(4-morpholine)ethyl]-1H-pyrrole-2-amide, trifluoroacetate
[0701] To 4-amino-1-methyl-N-[1-methyl-5-({[2-(4-morpholinyl)ethyl]amino}-carbonyl)-1H- dissolved in DMF (1 mL) Pyrrol-3-yl]-1H-pyrrole-2-amide (46 mg, 0.124 mmol; see Preparation 1 above) was added with stirring at room temperature HBTU (100 mg, 0.264 mmol), 4-[(E)-2-(3- Quinoline)vinyl]benzoic acid (34 mg, 0.123 mmol; see Preparation 5 above). The reaction mixture was left at room temperature overnight. The product was purified by HPLC (no workup) to afford the title compound (36 mg, 39%) as a pale yellow solid with no apparent melting point.
[0702] 1 H NMR (DMSO-d 6 ): 10.35(1H, s), 9.98(1H, s), 9.55(1H, br), 9.28(1H, d, J=2.0Hz), 8.59(1H, d, J=2.0Hz), 8.23(1H , t, J=8.0Hz), 8.05-7.97 (5H, m), 7.83-7.75 (4H; m), 7.70-7.60 (4H, m), 7.34 (1H, d, J=1.7Hz), 7.21 ( 1H, d, J = 1.7Hz), 7.13 (1H, d, J ...
Embodiment 3
[0706] 1-methyl-N-[1-methyl-5-{[2-(4-morpholinyl)ethyl]amino}carbonyl-1H-pyrrol-3-yl]-4-{[(4-( E)-2-(1-Methyl-1H-pyrrol-2-yl)vinyl]benzoyl}amino)-1H-pyrrole-2-amide, trifluoroacetate
[0707] (i) 1-methyl-4-{[(1-methyl-4-amino-1H-pyrrol-2-yl)carbonyl]amino}-N-[2-(4-morpholinyl)ethyl]-1H- Pyrrole-2-amide
[0708] 1-methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-N-[2-(4-morpholinyl)ethyl]- 1H-Pyrrole-2-amide (86 mg, 0.212 mmol; see Preparation 1(iv) above) was suspended in methanol (25 mL), to which Pd / C-10% (80 mg) was added with stirring at 0 °C under nitrogen. The reaction mixture was hydrogenated at room temperature and pressure for 4 hours. The catalyst was removed over celite and methanol was removed under reduced pressure to yield the amine, which was dissolved in DMF (1 mL, dry). The resulting amine was used in the next step without purification.
[0709] (ii) 1-methyl-N-[1-methyl-5-({[2-(4-morpholinyl)ethyl]amino)carbonyl}-1H-pyrrol-3-yl]-4-{[4- ...
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