Diisopropylethylamine → HCID 178461916, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-(7-chloro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine from Example 19 (482 mg, 1.77 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (466 mg, 1.95 mmol) and DIPEA (0.91 mL, 5.32 mmol) in IMS (3.5 mL) was stirred in a sealed vial for 48 h at 90° C. After cooling to RT, volatiles were removed under reduced pressure and the resulting residue was loaded into an Isolute® SCX-2 which was washed with MeOH followed by 2M NH3/MeOH. The product containing fractions (basic and methanolic) were combined and concentrated in vacuo. Purification by Isolute® SCX-2 was repeated a second time and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM). The basic fractions were combined and concentrated in vacuo and the residue was refluxed in MeOH. After cooling to RT the solid was filtered off and washed with EtOAc affording 138 as a white solid (379 mg, 55%). LCMS: RT 3.65 min [M+H]+ 390.0. 1H NMR (DMSO, 400 MHz): δ 8.20-8.06 (2H, m), 7.94 (1H, s), 7.69-7.36 (6H, m), 7.24-7.19 (2H, m), 5.26 (1H, bs), 1.10 (3H, d, J=7.00 Hz)

Provenance & Evidence