p-Toluenesulfonic acid monohydrate → HCID 178442277, compound

Participants

Reaction Conditions

Reaction Steps

(±)-tert-Butyl 4-(1-((2-amino-5-cyanophenyl)amino)-2-methyl-1-oxopent-4-en-2-yl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 156-E) (0.36 g, 0.737 mmol) was dissolved in toluene (2.76 mL) and dioxane (0.921 mL). p-Toluenesulfonic acid monohydrate (0.042 g, 0.221 mmol) was then added and the mixture heated at 135° C. for 3 hours. At this point another aliquot of p-toluenesulfonic acid monohydrate (0.030 g) was added and the reaction was heated for 1 hour. At this point another aliquot of p-toluenesulfonic acid monohydrate (0.025 g) was added and the reaction was heated for 1.5 hour. The reaction was then cooled to room temperature, concentrated and absorbed onto silica to purify via FCC(0-50% EtOAc:heptanes) to obtain the title compound that was used directly in the next step. MS (ESI+) m/z 371.4 (M+H).

Provenance & Evidence