Diisopropylethylamine → HCID 57407263, compound

Participants

Reaction Conditions

Reaction Steps

0.1 mmol N-cyclopropyl-4-[8-(methylsulfonyl)-6-(pyridin-4-yl)imidazo[1,2-a]pyrazin-3-yl]benzamide (intermediate example 9-2) (1 mL, 0.1 M in NMP), 0.2 mmol tert-butyl(3-aminopropyl)carbamate (0.4 mL, 0.5 M in NMP, 2 eq) and 0.3 mmol DIPEA (41 μL, 3 eq) were combined in a sealed vial and heated at 170° C. under microwave irradiation for 60 min. After cooling, the solution was filtered and subjected to preparative HPLC to give 8.9 mg tert-butyl [3-({3-[4-(cyclopropylcarbamoyl)phenyl]-6-(pyridin-4-yl)imidazo[1,2-a]pyrazin-8-yl}amino)propyl]carbamate (11%): 1H-NMR (300 MHz, d6-DMSO): δ=8.58 (2H, d), 8.54 (1H, d), 8.32 (1H, s), 8.02-7.93 (3H, m), 7.87-7.76 (4H, m), 6.83 (1H, tr), 3.58 (2H, m), 3.01 (2H, m), 2.86 (1H, m), 1.77 (2H, m), 1.32 (9H, s), 0.68 (2H, m), 0.55 (2H, m) ppm; UPLC-MS: RT=0.90 min; m/z (ES+) 528.6 [MH+]; required MW=527.6.

Provenance & Evidence