Benzylamine → HCID 86616741, compound

Participants

Reaction Steps

A solution of 5-(5-amino-1H-pyrrolo[2,3-c]pyridin-3-yl)-1H-indazole-7-carboxylic acid hydrochloride (Preparation #13, 32.9 mg, 0.10 mmol) and benzylamine (24.0 μL, 0.22 mmol) in DMF (1.0 mL) were treated with o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (38.0 mg, 0.10 mmol) at ambient temperature and the reaction was stirred for about 1 hour. The reaction was concentrated under reduced pressure and the residue was purified by preparative HPLC (Waters Symmetry C8 column (25×100 mm, 7 μm particle size) using a gradient of 10%-100% CH3CN/0.1% aqueous TFA over 8 min (10 min run time) at a flow rate of 40 mL/min). Product fractions were combined and concentrated to remove organic solvents and then lyophilized to yield N-benzyl 5-(5-amino-1H-pyrrolo[2,3-c]pyridin-3-yl)-1H-indazole-7-carboxamide acetate (10 mg, 23%) as an off-white powder; RP-HPLC (Table 1, Method e) Rt 1.94 min; m/z: (M−H)− 381.

Provenance & Evidence