p-Toluenesulfonic acid → 1-(Chloromethyl)-N-(2-hydroxyethyl)-5-nitro-3-(5,6,7-trimethoxyindol-2-carbonyl)-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide

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Reaction Steps

Amine 121 (75 mg, 0.19 mmol) was dissolved in MeOH/HCl(g) at room temperature and the solution was evaporated to dryness under reduced pressure. 5,6,7-Trimethoxyindole-2-carboxylic acid (59 mg, 0.23 mmol), EDCI (149 mg, 0.78 mmol), anhydrous TsOH (30 mg, 0.17 mmol) and dry DMA (3 mL) were then added, and the mixture was stirred at room temperature for 1 h. The mixture was poured into water and the precipitate was collected and washed with water, dried, and dissolved in the minimum volume of DMW at room temperature. The solution was diluted with EtOAc, filtered, and then diluted with hexane and refrigerated to give 33 (89 mg, 74%): mp 257-258° C.; 1H NMR [(CD3)2SO] δ 11.61 (s, 1H), 9.24 (s, 1H), 8.86 (d, J=1.6 Hz, 1H), 8.43 (d, J=8.9 Hz, 1H), 8.02 (dd, J=8.9, 1.7 Hz, 1H), 7.91 (t, J=5.7 Hz, 1H), 7.20 (d, J=2.1 Hz, 1H), 6.99 (s, 1H), 4.93 (t, J=10.1 Hz, 1H), 4.70-4.58 (m, 3H), 4.18-4.07 (m, 2H), 3.94 (s, 3H), 3.83 (s, 3H), 3.81 (s, 3H, 3.39 (q, J=6.0 Hz, 2H), 2.88 (q, J=6.1 Hz, 2H). Anal. (C27H27ClN4O9S) C, H, N.

Provenance & Evidence