Water → HCID 86677961, compound

Participants

Reaction Steps

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 (210 mg, 0.382 mmol) was dissolved in a 4:6 solution of TFA:DCM (57 mL). After stirring at room temperature overnight, the volatiles were removed under reduced pressure. The crude material was then dissolved in dichloromethane and treated with ethylenediamine (229 mg, 3.82 mmol). After stirring at room temperature overnight, water was added and the resulting precipitate was collected by filtration to give 140 mg (87%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(2-cyano-cyclopropyl)-ethyl]-amide (diastereomer A) as a light yellow solid. MS: (M+H)+=420. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.70 (bs, 1H) 9.08 (s, 4H) 8.32-8.58 (m, 2H) 8.13 (dd, J=12.27, 8.12 Hz, 1H) 7.98 (s, 1H) 7.24-7.44 (m, 1H) 4.16 (s, 3H) 3.80 (d, J=5.29 Hz, 1H) 1.61-1.96 (m, 2H) 1.40 (m, 3H) 0.98-1.30 (m, 2H).

Provenance & Evidence