Diisopropylethylamine → HCID 68283608, compound

Participants

Reaction Steps

To a solution of (3-carbamoyl-pyrazolo[3,4-c]pyridin-1-yl)-acetic acid trifluoroacetate salt (2.65 g, 7.94 mmol, prepared as described in Scheme A26) in DMF (30 mL) were added successively (1R,3S,5R)-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid, [(R)-1-(3-chloro-2-fluoro-phenyl)-ethyl]-amide trifluoroacetate salt (3.00 g, 7.56 mmol), HBTU (3.44 g, 9.07 mmol) and DIPEA (5.28 mL, 30.2 mmol). The reaction mixture was stirred at RT for 16 h and then was concentrated under vacuum. The residual oil was partitioned between CH2Cl2 and a sat. aq. NaHCO3 solution. A solid precipitated from the resulting emulsion and was filtered off, washed with water and dried under vacuum. The solid was suspended in a mixture of water (150 mL) and MeOH (3 mL), stirred for 1 h at RT, filtered, washed with water and finally dried under vacuum to give the title material as a white powder. MS (LC/MS): 485 [M+H]+; tR (HPLC conditions c): 3.54 min.

Provenance & Evidence