Diisopropylethylamine → HCID 58557125, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-8-(piperidin-3-yl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine hydrobromide and (S)-8-(piperidin-3-yl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine hydrobromide [er=80:20](0.30 g, 0.93 mmol), DIEA (0.52 mL, 3.0 mmol) and 3,3-difluorocyclobutanecarboxylic acid (0.35 g, 3.1 mmol, Waterstone) in DMF (4 mL) was added EDC•HCl (0.21 g, 1.1 mmol). The reaction was stirred at about 25° C. for about 4 h. The reaction was partitioned with aqueous Na2CO3 (2 M, 25 mL) and DCM (25 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concd in vacuo. The resulting residue was purified on silica gel (12 g) using 0-5% MeOH in DCM followed by purification using General Procedure AA (Table 2, Method 23, Rt=16.4 min, or =positive) to give (R)-(3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)piperidin-1-yl)(3,3-difluorocyclobutyl)-methanone (0.10 g, 30%): LC/MS (Table 1, Method b) Rt=1.85 min; MS m/z: 360 (M+H)+.

Provenance & Evidence