1-Propanol → HCID 58382079, compound

Participants

Reaction Conditions

Reaction Steps

The (4-methoxyphenyl)(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanone (2.25 g, 5.52 mmol, prepared using AT from Preparation #AF.1) was dissolved in 1,4-dioxane (25 mL) and PrOH (5 mL) then treated with 4-methylbenzenesulfonohydrazide (1.08 g, 5.80 mmol). The mixture was heated to about 100° C. for about 2 h then it was treated with 1 drop concentrated HCl. The mixture was stirred about 1 h at about 100° C. and then the mixture was concentrated under reduced pressure. The material was dissolved in morpholine (15.0 mL, 172 mmol) then the mixture was heated to about 100° C. for about 15 min. The mixture was cooled to rt and concentrated on the under reduced pressure. The material was treated with water (100 mL) and EtOAc (˜40 mL). The mixture was stirred for about 10 min then filtered. The solids were washed with EtOAc (˜7 mL) then dried to a constant weight under vacuum at about 70° C. to give 3-(4-methoxyphenyl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,3]triazolo[1,5-a]pyrazine (0.760 g, 33%): LC/MS (Table 2, Method a) Rt=2.74 min; MS m/z 420 (M+H)+.

Provenance & Evidence