Water → HCID 69932045, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-chloro-2-(3-methylquinoxalin-2-yl)-N-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine (Example 1.001 (g)) (398 mg, 1.01 mmol) and (s)-3-hydroxypyrrolidine (351 mg, 4.03 mmol) in N-methyl-2-pyrrolidinone (5.0 mL) was heated at 80° C. for 6 h. Then the reaction mixture was poured into cold water. The resulting precipitate was collected and purified by silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=7:3) to give 1-[2-(3-methylquinoxalin-2-yl)-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-3-ol (the compound of Example 1.007 listed in the Table of Examples as described hereinafter). 1H-NMR (500 MHz, CDCl3): δ 1.74-1.81 (2H, m), 2.12-2.22 (4H, m), 3.03 (3H, s), 3.58 (2H, dt, J=2.3, 11.9 Hz), 3.65-3.76 (5H, m), 4.08 (2H, dt, J=11.6, 3.2 Hz), 4.64-4.67 (1H, m), 5.16 (1H, s), 6.16 (1H, d, J=8.0 Hz), 6.66 (1H, s), 7.70-7.76 (2H, m), 8.03-8.05 (1H, m), 8.17-8.19 (1H, m).

Provenance & Evidence