HCID 18446603, compound → Cyclopentylamine

Participants

Reaction Steps

N-Cyclopentyl-4-{2-[2-(isopropylamino)-4-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl}-2-pyrimidinamine. In a similar manner as described in example 17 from 2-(2-fluoro-4-pyridinyl)-3-[2-(methylsulfinyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridine (410 mg, 1.16 mmol) and cyclopentylamine (4 mL, 40.5 mmol) was formed crude N-cyclopentyl-4-[2-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine (385 mg), of which 260 mg (0.694 mmol) was dissolved in isopropylamine (3 mL, 35.2 mmol) and heated at 150° C. in a steel bomb for 16 hours. The reaction mixture was cooled and the excess isopropylamine was removed under a stream of nitrogen to provide N-cyclopentyl-4-{2-[2-(isopropylamino)-4-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl}-2-pyrimidinamine (170 mg, 52% for 2 step procedure) as a beige solid. 1H NMR (CDCl3) δ 8.50 (d, 1H), 8.41 (d, 1H), 8.13–8.08 (m, 2H), 7.32 (t, 1H), 6.92 (t, 1H), 6.80 (d, 1H), 6.62 (s, 1H), 6.47 (d, 1H), 5.26 (d, 1H), 4.63 (d, 1H), 4.34 (m, 1H), 3.85 (m, 1H), 2.11–2.04 (m, 2H), 1.79–1.51 (m, 6H), 1.22 (d, 6H); MS m/z 414 (M+1).

Provenance & Evidence