Diisopropylethylamine → HCID 68156905, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-[6-fluoro-1-(2-methoxyethyl)-7-pyridin-2-yl-1H-benzoimidazol-2-yl]ethylamine (167 mg, 0.53 mmol), 4-amino-6-chloropyrimidine-5-carbonitrile (86 mg, 0.56 mmol) and DIPEA (0.28 mL, 1.6 mmol) in IPA (1 mL) was heated for 16 h at 90° C. After cooling to RT, the volatiles were removed under reduced pressure and the resulting residue loaded onto an Isolute® SCX-2 cartridge. The cartridge was 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—PPC, gradient 0-10% 2M NH3 in MeOH/DCM) to afford 420 as a white solid (146 mg, 63%). LCMS (Method K): RT 3.15 min [M+H]+ 433. 1H NMR (DMSO-d6, 400 MHz): δ 8.73 (1H, ddd, J=5.0, 2.0, 1.0 Hz), 8.03 (1H, s), 7.97 (1H, ddd, J=7.5, 7.5, 2.0 Hz), 7.74 (1H, dd, J=9.0, 5.0 Hz), 7.70-7.66 (2H, m), 7.51 (1H, ddd, J=7.5, 5.0, 1.0 Hz), 7.30 (2H, bs), 7.18 (1H, dd, J=10.5, 9.0), 5.69 (1H, dq, J=6.5, 6.5 Hz), 4.14-4.07 (1H, m), 3.82 (1H, ddd, J=15.0, 5.0, 5.0 Hz), 3.07-2.99 (2H, m), 2.93 (1H, s), 1.59 (3H, d, J=6.5 Hz)

Provenance & Evidence