Tert-Butylamine → 3-(7-(tert-butylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazole 2-oxide

Participants

Reaction Conditions

Reaction Steps

In a 16×100 mm screw cap test tube were added HATU (46.3 mg, 122 μmol.20) and 2-methylpropan-2-amine (29.7 mg, 406 μmol) then 3-(7-carboxy-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazole 2-oxide (45 mg, 101 μmol) dissolved in DMF (2.00 mL) was added to give a light yellow solution which immediately formed a white precipitated. The reaction mixture stirred at 25° C. overnight, solvents evaporated and residue purified by chromatography (spherical silica 20-45 μm, 23 g, Versaflash Supelco) eluting with 0 to 50% EtOAc in hexanes over 30 min to yield 3-(7-(tert-butylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazole 2-oxide (43 mg, 86.2 μmol, 85.0%) as a clear foam. MS (M+H)+=499 (>90% purity); 1H NMR (CDCl3) δ: 7.82 (s, 1H), 6.21 (s, 1H), 4.52 (s, 2H), 2.36-2.45 (m, 2H), 2.30 (s, 3H), 1.23-1.37 (m, 2H), 0.95-1.12 (m, 2H), 0.89 (dd, J=10.9, 5.6 Hz, 2H), 0.72-0.85 (m, 2H), 0.37 (s, 9H), −0.29-−0.17 (m, 2H), −1.20 (s, 9H).

Provenance & Evidence