PMC:7571312 / 47289-48508 5 Projects
Annnotations
| Id | Subject | Object | Predicate | Lexical cue |
|---|---|---|---|---|
| T314 | 0-177 | Sentence | denotes | A solution of the crude hydrochloride salt and 4-methoxy-1H-indole-2-carboxylic acid (123 mg, 0.64 mmol) in DMF (2.5 mL) was placed under an atmosphere of N2 and cooled to 0 °C. |
| T315 | 178-328 | Sentence | denotes | This pale yellow solution was successively treated with HATU (245 mg, 0.64 mmol) and N-methylmorpholine (0.14 mL, 1.29 mmol) turning a brighter color. |
| T316 | 329-454 | Sentence | denotes | After 30 min, the reaction was quenched with 1:1 ice/sat NaHCO3 (25 mL) and extracted three times with ethyl acetate (20 mL). |
| T317 | 455-582 | Sentence | denotes | The combined organics were washed once with brine (30 mL), dried over MgSO4, filtered, and concentrated to give a yellow syrup. |
| T318 | 583-727 | Sentence | denotes | This material was purified by LC (30 g 230–400 SiO2, 4% methanol/chloroform) to afford 167 mg (58%) of the title compound as an off-white solid. |
| T319 | 728-1219 | Sentence | denotes | 1H NMR (DMSO-d6) δ 11.59 (s, 1H), 8.62 (d, J = 8 Hz, 1H), 8.44 (d, J = 4 Hz, 1H), 7.65 (s, 1H), 7.38 (s, 1H), 7.10 (t, J = 8 Hz, 1H), 7.02 (d, J = 8 Hz, 1H), 6.51 (d, J = 8 Hz, 1H), 4.60 (d, J = 16 Hz, 1H), 4.58 (d, J = 16 Hz, 1H), 4.46 (m, 2H), 3.89 (s, 3H), 3.11 (m, 2H), 2.29 (m, 1H), 2.11 (m, 1H), 1.99 (m, 1H), 1.76–1.54 (m, 5H), 0.95 (d, J = 8 Hz, 3H), 0.9 (d, J = 8 Hz, 3H); MS (ESI+) for C24H31ClN4O5m/z 491.1 (M + H)+; HRMS (ESI+) calcd for C24H31ClN4O5+H1 491.2056, found 491.2058. |