1-Hydroxybenzotriazole → HCID 86677960, compound

Participants

Reaction Steps

2-((R)-1-Amino-ethyl)-cyclopropanecarbonitrile trifluoroacetate, diastereomer A (crude from Step 2) was treated with 1-hydroxybenzotriazole (153 mg, 1.14 mmol), 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (662 mg, 1.75 mmol,), DIPEA (0.76 ml, 4.37 mmol), 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (400 mg, 0.87 mmol) and DMF (6.0 ml) to give a light yellow solution. After stirring at room temperature overnight, the reaction mixture was diluted with ethyl acetate and water. The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, EtOAc in heptane gradient) to provide 210 mg (44%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(2-cyano-cyclopropyl)-ethyl]-amide (diastereomer A) as a colorless oil. MS: (M+H)+=551.

Provenance & Evidence