1,1'-Carbonyldiimidazole → HCID 68182919, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1S,2R)-2-(4-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)butanamido)bi(cyclopropane)-2-carboxylic acid (15 mg, 0.02 mmol) in THF solution was added CDI (7.0 mg, 0.04 mmol). The mixture was heated at 65° C. for 1 hour. After cooling to room temperature, methanesulfonamide (4.2 mg, 0.04 mmol) and DBU (9.9 ul, 0.07 mmol) were added to the mixture. The reaction mixture was stirred at r.t. for 16 hours. The solvent was evaporated and the residue was purified by preparative HPLC to afford 4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-N-(4-((1S,2R)-2-(methylsulfonylcarbamoyl)bi(cyclopropan)-2-ylamino)-4-oxobutyl)benzamide (6.7 mg, 40%) as a white solid. 1H NMR (400 MHz, MeOD) δ ppm 0.34 (m, 2H), 0.57 (q, J=9.20 Hz, 2H), 0.71-0.80 (m, 1H), 1.08-1.13 (m, 1H), 1.18 (ddd, J=9.41, 7.53, 7.40 Hz, 1H), 1.34-1.45 (m, 4H), 1.77 (dd, J=7.53, 5.02 Hz, 1H), 1.85-1.97 (m, 1H), 2.26-2.36 (m, 2H), 2.37 (m, 2H), 3.26 (s, 3H), 3.41-3.51 (m, 1H), 4.00 (s, 2H), 7.23-7.33 (m, 4H), 7.60-7.75 (m, 3H), 7.85 (m, 1H); LC-MS (Condition A), MS m/z 765.1 (M++H).

Provenance & Evidence