Diisopropylethylamine → HCID 178461951, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-(6-fluoro-1-methyl-7-pyridin-2-yl-1H-benzoimidazol-2-yl)ethylamine (100 mg, 0.37 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (88 mg, 0.37 mmol) and DIPEA (340 μL, 1.85 mmol) in IPA (5 mL) were added and the reaction mixture heated at 90° C. for 16 h. The reaction mixture was loaded onto an SCX column to remove the THP group. The column was washed with MeOH and the product was eluted with 2M NH3 in MeOH. The product fractions were collected, concentrated in vacuo and the resultant residue was subjected to flash chromatography (Si—PPC, gradient 0-5% MeOH in DCM) to give 413 as a white solid (67 mg, 47%). LCMS (Method K): RT 2.53 min [M+H]+ 389. 1H NMR (DMSO-d6, 400 MHz): δ 12.7 (1H, br s), 8.68 (1H, ddd, J=4.8, 1.7, 0.8 Hz), 8.13 (2H, d, J=21.9 Hz), 7.91 (1H, br s), 7.90 (1H, td, J=7.8, 1.8 Hz), 7.65 (1H, dd, J=8.8, 4.8 Hz), 7.60 (1H, tq, J=7.7, 1.1 Hz), 7.44 (1H, ddd, J=7.5, 4.8, 1.1 Hz), 7.10 (1H, dd, J=10.4, 8.8 Hz), 5.82-5.67 (1H, m), 3.15 (3H, s), 1.61 (3H, d, J=6.7 Hz)

Provenance & Evidence