Methyl iodide → HCID 18617801, compound

Participants

Reaction Steps

t-Butyl 5-[2-[4-(3-t-butoxycarbonylaminoprop-1-ynyl)-benzoylamino]ethyl}-3-thiocarbamoyl-indole-1-carboxylate (73 mg, 0.13 mmol, reference example 78) is dissolved in acetone (75 mL) and methyl iodide (5 mL) added. This mixture is heated to reflux. After 15 minutes, the solvent is removed in vacuo giving a yellow residue. MS (ion spray) m/e 591 (M+H+). The residue (80 mg, 0.13 mmol) is dissolved in MeOH (15 mL) and ammonium acetate (0.5 g) added and this mixture heated at reflux for 20 minutes. The solvent is removed in vacuo and the residue partitioned between CH2Cl2 and water. The aqueous layer is extracted with CH2Cl2 and the combined organic layers washed with water, dried over magnesium sulfate and concentrated in vacuo. The crude product is purified by reverse phase HPLC eluting with 30-70%/15 minutes, giving 22 mg. MS (ion spray) m/z 560 (M+H+).

Provenance & Evidence