Trifluoroacetic acid → HCID 71280356, compound

Participants

Reaction Steps

To a stirred solution of N-tert-butyl-2-(5-(difluoromethoxy)-1-((4-methylmorpholin-2-yl)methyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (63 mg, 97.9 μmol) in dichloromethane (2 mL) was added trifluoroacetic acid (1 mL). After stirring at room temperature for 15 h the mixture was concentrated in vacuo then 25 mL Jan. 10, 1960 mixture of ammonium hydroxide/methanol/dichloromethane was added. After 1 h the mixture was concentrated and purified by chromatography (silica, 24 g Analogix column, 0-4% methanol containing 10% ammonium hydroxide in dichloromethane) to give 2-[5-difluoromethoxy-1-(4-methyl-morpholin-2-ylmethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (22 mg, 43%). MS (M+H)+=514; 1H NMR (DMSO-d6) δ: 9.07 (s, 1H), 8.39 (s, 1H), 8.19 (d, J=2.3 Hz, 1H), 7.89 (s, 1H), 7.86 (s, 1H), 7.39 (dd, J=9.0, 2.3 Hz, 1H), 7.20 (s, 1H), 4.58-4.68 (m, 2H), 3.74 (d, J=11.9 Hz, 1H), 3.37-3.48 (m, 1H), 2.79 (d, J=11.3 Hz, 1H), 2.57 (br. s., 3H), 2.18 (s, 3H), 1.84-2.01 (m, 1H), 1.51 (s, 9H).

Provenance & Evidence