Diisopropylethylamine → HCID 178463566, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-[2-((S)-1-aminoethyl)-6-fluorobenzoimidazol-1-yl]azetidine-1-carboxylic acid tert-butyl ester (354 mg, 1.05 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (278 mg, 1.16 mmol) and DIPEA (0.41 mL, 3.18 mmol) in n-butanol (1.4 mL) was heated at 90° C. in a sealed vial for 16 h. After cooling to RT, the volatiles were removed under reduced pressure and the resulting residue loaded onto an Isolute® SCX-2 cartridge and washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined, concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-5% MeOH in DCM) to afford 377 as a white solid (214 mg, 71%). LCMS (Method K): RT 3.59 min [M+H]+ 453.1. 1H NMR (DMSO-d6, 400 MHz): δ 12.43 (1H, s), 8.23 (1H, br s), 8.14 (1H, br s), 7.96 (1H, d, J=7.67 Hz), 7.68 (1H, dd, J=8.83, 5.02 Hz), 7.36 (1H, dd, J=9.41, 2.45 Hz), 7.11 (1H, td, J=9.29, 2.36 Hz), 5.79 (1H, br s), 5.70-5.60 (1H, m), 4.48-4.34 (2H, m), 4.31-4.19 (2H, m), 1.65 (3H, d, J=6.67 Hz), 1.44 (9H, s)

Provenance & Evidence