Methanesulfonamide → HCID 178480011, compound

Participants

Reaction Steps

1-Methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-5-carboxylic acid (0.047 g, 0.14 mmol, Example #AN.1), methanesulfonamide (0.039 g, 0.41 mmol) and EDC (0.065 g, 0.34 mmol) were combined in a mixture of DCE (1.31 mL) and t-BuOH (1.31 mL). DMAP (0.050 g, 0.41 mmol) was added and the mixture was stirred at rt for about 16 h. The mixture was purified by flash chromatography (12 g silica gel column, (6:3:1 CHCl3/MeOH/saturated NH4OH)/EtOAc 50-85%) to give 1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-N-(methylsulfonyl)-1H-indole-5-carboxamide (0.024 g, 42%): LC/MS (Table 2, Method a) Rt=1.55 min; MS m/z 423 (M+H)+. Syk IC50=A.

Provenance & Evidence