N-((3S,4S)-4-fluoro-1-(9-isopropyl-6-((1-methyl-1H-pyrazol-4-yl)amino)-9H-purin-2-yl)pyrrolidin-3-yl)acrylamide → N-((3R,4R)-4-fluoro-1-(9-isopropyl-6-((1-methyl-1H-pyrazol-4-yl)amino)-9H-purin-2-yl)pyrrolidin-3-yl)acrylamide

Participants

Reaction Steps

N-((3S,4S)-4-fluoro-1-(9-isopropyl-6-((1-methyl-1H-pyrazol-4-yl)amino)-9H-purin -2-yl)pyrrolidin-3-yl)acrylamide, 36.7 mg, 9% yield (in 3 steps), >99% ee, 95% pure. Optical rotation: [α]D22=−19.06° (c 0.08, EtOH). 1H NMR (600 MHz, DMSO-17 mm) δ ppm 9.65 (br. s., 1 H) 8.50 (d, J=6.42 Hz, 1 H) 8.00 (s, 1 H) 7.92 (s, 1 H) 7.69 (s, 1 H) 6.19-6.29 (m, 1 H) 6.11-6.18 (m, 1 H) 5.63 (d, J=11.92 Hz, 1 H) 5.08-5.22 (m, 1 H) 4.46-4.69 (m, 2 H) 3.88 (br. s., 2 H) 3.82 (s, 3 H) 3.64-3.79 (m, 2 H) 1.50 (d, J=6.79 Hz, 6 H). m/z (APCI+) for C19H24FN9O 414.1 (M+H)+.

Provenance & Evidence