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Benzoyl chloride (32.6 mg, 0.186 mmol) plus the EZH1 list ynamide (32.5 mg, 0.12 mmol) was performed at 30 for 18 h. The concentrated crude residue wasEXPERIMENTAL SECTIONpurified by column chromatography (five:two dichloromethane/hexanes) to give 45 mg (0.11 mmol, 92 ) of a white solid. 1H NMR (400 MHz): eight.06 (d, J = 7.6 Hz, 1H), 7.60 (d, J = eight.3 Hz, 2H), 7.45 (d, J = three.six Hz, 2H), 7.45-7.31 (m, 4H), 7.31-7.21 (m, 4H), 2.43 (s, 3H). 13C NMR (one hundred MHz): 175.3, 145.9, 137.1, 135.4, 133.1, 133.0, 132.9, 132.4, 131.4, 129.9, 129.4, 129.2, 128.2, 126.8, 126.5, 91.0, 76.three, 21.7. Anal. Calcd For C22H16ClNO3S: C, 64.47; H, three.93; N, 3.42. Discovered: C, 64.65; H, 4.07; N, three.41. Mp 105 (decomp) N-(3-(4-Chlorophenyl)-3-oxoprop-1-ynyl)-N-phenyl-4-tolylsulfonamide, 4. The reaction with 4-chlorobenzoyl chloride (31.four mg, 0.18 mmol) as well as the ynamide (32.five mg, 0.12 mmol) was performed at 30 for 20 h. The concentrated crude residue was purified by column chromatography (2:1 dichloromethane/hexanes) to give 47 mg (0.115 mmol, 96 ) of a white strong. 1H NMR (400 MHz): eight.09 (d, J = eight.6 Hz, 2H), 7.57 (d, J = 8.4 Hz, 2H), 7.45 (d, J = 8.5 Hz, 2H), 7.39-7.28 (m, 3H), 7.28-7.18 (m, 4H), two.39 (s, 3H). 13C NMR (100 MHz): 175.4, 146.0, 140.two, 137.0, 135.4, 132.9, 130.5, 129.9, 129.5, 129.3, 128.9, 128.1, 126.4, 90.7, 74.7, 21.6. Anal. Calcd For C22H16ClNO3S: C, 64.47; H, three.93; N, 3.42. Identified: C, 64.38; H, four.05; N, 3.46. Mp Dynamin Formulation 105-107 . N-(3-(4-Cyanophenyl)-3-oxoprop-1-ynyl)-N-phenyl-4-tolylsulfonamide, 5. The reaction with 4-cyanobenzoyl chloride (30.0 mg, 0.18 mmol) as well as the ynamide (32.7 mg, 0.12 mmol) was performed at 30 for 18 h. The concentrated crude residue was purified by column chromatography (3:1 dichloromethane/hexanes) to give 46.5 mg (0.116 mmol, 97 ) of a white strong. 1H NMR (400 MHz): 8.29 (d, J = 8.three Hz, 2H), 7.82 (d, J = eight.1 Hz, 2H), 7.60 (d, J = 8.three Hz, 2H), 7.47-7.34 (m, 3H), 7.29 (d, J = eight.1 Hz, 2H), 7.27-7.23 (m, 2H), 2.43 (s, 3H). 13C NMR (one hundred MHz): 174.8, 146.two, 139.8, 136.8, 136.7, 132.8, 132.4, 130.0, 129.6, 129.4, 128.1, 126.4, 117.9, 116.eight, 92.3, 75.1, 21.7. Anal. Calcd For C23H16N2O3S: C, 68.98; H, four.03; N, 7.00. Located: C, 68.67; H, four.14; N, six.92. Mp 155 (decomp) N-(3-(2-Naphthyl)-3-oxoprop-1-ynyl)-N-phenyl-4-tolylsulfonamide, 6. The reaction with 2-naphthoyl chloride (35.0 mg, 0.18 mmol and also the ynamide (32.9 mg, 0.121 mmol) was performed at 30 for 12 h. The concentrated crude residue was purified by column chromatography (1:1 dichloromethane/hexanes) to offer 51.five mg (0.12 mmol, 99 ) of a white strong. 1H NMR (400 MHz): 8.88 (s, 1H), 8.19 (dd, J = eight.six, 1.7 Hz, 1H), eight.06 (d, J = eight.1 Hz, 1H), 7.94 (d, J = 8.7 Hz, 1H), 7.91 (d, J = 8.0 Hz, 1H), 7.65 (d, J = eight.two Hz, 2H), 7.65-7.54 (m, 2H), 7.44-7.34 (m, 3H), 7.35-7.27 (m, 2H), 7.28-7.22 (m, 2H), 2.41 (s, 3H). 13C NMR (100 MHz): 176.8, 145.9, 137.1, 135.9, 134.five, 132.9, 132.6, 132.5, 130.0, 129.9, 129.5, 129.two, 128.8, 128.4, 128.1, 127.8, 126.8, 126.six, 123.6, 90.two, 75.0, 21.7. Anal. Calcd For C26H19NO3S: C, 73.39; H, 4.50; N, three.29. Identified: C, 73.32; H, four.77; N, 3.32. N-(3-(1-Naphthyl)-3-oxoprop-1-ynyl)-N-phenyl-4-tolylsulfonamide, 7. The reaction with 1-naphthoyl chloride (55.0 mg, 0.dx.doi.org/10.1021/jo500365h | J. Org. Chem. 2014, 79, 4167-The Journal of Organic Chemistrymmol) along with the ynamide (54.five mg, 0.20 mmol) was performed at 20 for 38 h. The concentrated crude residue was purified by column chromatography (1:1 dichloromethane/hexanes) to provide 67 mg (0.16 mmol, 79 ) of a colorless oil. 1H N.