1,2-Dichloroethane → HCID 118126849, compound

Participants

Reaction Steps

1-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyrimidin-2-yl]amino}cyclopropanecarboxylic acid (177 mg, 0.411 mmol, as prepared in Example 2.3), ammonium chloride (66 mg, 1.2 mmol), EDC (0.158 g, 0.823 mmol), HOBT (0.111 g, 0.823 mmol), N,N-diisopropylethylamine (0.359 mL, 2.06 mmol) and DMF (4 mL) were combined and stirred at rt for 14 hours. The reaction mixture was concentrated in vacuo, then diluted with water and extracted with EtOAc (2×). The combined organic portions were washed with saturated sodium bicarbonate, then brine. The organic portions were collected and dried with MgSO4, filtered, and concentrated in vacuo to afford a brown solid. The residue was diluted with 1:1 CH2Cl2:hexanes and stirred for 10 min, then filtered. The solid was washed with 1:1 CH2Cl2:hexanes, then methanol to afford 1-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyrimidin-2-yl]amino}cyclopropanecarboxamide. MS ESI calcd. for C20H19F3N2O [M+H]+ 430. found 430. 1H NMR (500 MHz, DMSO-d) δ 10.22 (s, 1H), 8.82 (d, J=4.8 Hz, 1H), 8.60-8.55 (m, 2H), 7.85 (s, 1H), 7.82 (s, 1H), 7.47 (s, 1H), 7.26 (d, J=4.9 Hz, 1H), 7.17 (s, 1H), 7.11 (s, 1H), 6.92 (s, 1H), 2.32 (s, 3H), 1.33 (d, J=3.3 Hz, 2H), 0.92 (d, J=3.2 Hz, 2H).

Provenance & Evidence