cis-4-(7-{[2-({4-[(Diethoxyphosphoryl)methyl]-2-methoxyphenyl}amino)-5-(trifluoromethyl)pyrimidin-4-yl]amino}-2-methyl-1-oxo-2,3-dihydro-1H-isoindol-4-yl)cyclohexanecarboxylic acid (10.0 mg, 0.0142 mmol), TBTU (9.1 mg, 0.0283 mmol) and DMF (0.8 mL) were mixed and the mixture was stirred at room temperature for 30 minutes. Methylammonium chloride (9.6 mg, 0.142 mmol) and DIPEA (24.7 μL, 0.142 mmol) were added and the mixture was stirred at room temperature for 2 hours. The crude was purified by MDP to obtain the title compound (4.4 mg, 43% yield). 1H NMR (400 MHz, methanol-d4) δ=1.29 (t, J=7.1 Hz, 6H), 1.67-1.81 (m, 4H), 1.87-2.01 (m, 2H), 2.15 (d, J=12.4 Hz, 2 H), 2.60 (br. s., 1H), 2.71 (t, J=11.2 Hz, 1H), 2.79 (s, 3H), 3.18 (s, 3H), 3.37 (d, J=21.7 Hz, 2H), 3.90 (s, 3H), 4.10 (quin, J=7.3 Hz, 4H), 4.53 (s, 2H), 6.99 (d, J=7.8 Hz, 1H), 7.13 (s, 1H), 7.34 (br. s., 1H), 7.67 (d, J=8.1 Hz, 1H), 8.33 (br. s., 2H). MS (ES+): m/z 719.36 (100) [MH+]; HPLC: tR=1.04 min (UPLC, purity).
