Sulfamic Acid → HCID 71279931, compound

Participants

Reaction Conditions

Reaction Steps

In a 50 mL round-bottomed flask, sulfamic acid (187 mg, 1.54 mmol) and 2-(5-chloro-benzoimidazol-1-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (110 mg, 0.26 mmol) were combined with dioxane (6 ml) to give a off-white suspension. The reaction mixture was cooled to 5° C. and a solution of sodium chlorite (30.2 mg, 0.33 mmol) and potassium dihydrogen phosphate (35.0 mg, 0.26 mmol) in water (2 ml) was added dropwise via syringe over 5 min. The reaction warmed to room temperature and stirred for 1 h. The reaction was diluted with EtOAc (25 ml) and washed with 50% brine/water. The aqueous layer was back-extracted with EtOAc (15 mL). The organic layers were combined, washed with brine and dried (MgSO4). Evaporation of the solvent gave 90 mg (79%) of 2-(5-chloro-benzoimidazol-1-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid as a solid. (M+H)+=444.

Provenance & Evidence