Diisopropylethylamine → HCID 68157294, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-[6-fluoro-1-(2-methyl-2H-pyrazol-3-yl)-1H-benzoimidazol-2-yl]ethylamine, (0.093 g, 0.359 mmol), 4-amino-6-chloropyrimidine-5-carbonitrile (0.078 g, 0.502 mmol) and DIPEA (0.12 mL, 0.646 mmol) in IPA (2 mL) was stirred at 80° C. in a sealed microwave tube for 16 h. After cooling, mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH then concentrated in vacuo. Residue was purified by silica gel chromatography eluting with 100% DCM—8% (2M ammonia in methanol) in DCM to give 416 as a white solid (0.107 g, 79%). LCMS (Method K): RT 3.16, 3.28 min [M+H]+ 378.0. 1H NMR (DMSO-d6, 400 MHz): δ 7.92-7.87 (1H, s), 7.87-7.84 (1H, m), 7.75-7.75 (1H, m), 7.60-7.54 (1H, m), 7.30-7.19 (3H, m), 6.96 (1H, m), 6.61-6.44 (1H, m), 5.47-5.38 (1H, m), 3.59-3.53 (3H, m), 3.17 (0H, d, J=5.25 Hz), 1.58-1.51 (3H, m). Signals split due to presence of rotamers/tautomers

Provenance & Evidence