Diisopropylethylamine → HCID 58382191, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzoic acid (0.10 g, 0.22 mmol, prepared using D from Preparation #1 with 3-boronobenzoic acid), DIEA (0.039 mL, 0.224 mmol), HATU (0.085 g, 0.224 mmol) and DMF (3 mL). The mixture was stirred at about 40° C. for about 30 min. To the mixture was added 2-morpholinoethanamine (0.038 mL, 0.291 mmol). The mixture was allowed to stir at about 40° C. for about 2 h. The mixture was stirred overnight at rt and then diluted with EtOAc (10 mL) and washed with water (10 mL). The aqueous layer was further extracted with EtOAc (2×10 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography with an elution gradient of 0 to 7.5% MeOH/DCM to give 3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-N-(2-morpholinoethyl)benzamide (0.123 g, 98%): LC/MS (Table 2, Method c) Rt=1.20 min; MS m/z 559 (M+H)+.

Provenance & Evidence