Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate → HCID 178476871, compound

Participants

Reaction Steps

The title product was prepared according to the procedure for Example 102 using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate (40.0 mg, 0.0944 mmol) and 7-amino-4-(cis-4-ethoxycyclohexyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one (Compound 166A, 32.67 mg, 0.1133 mmol). The reaction mixture was concentrated under reduced pressure to yield a yellow oil. The material was purified by silica gel chromatography on the combi-flash Rf system using 1:1 EtOAc-DCM/MeOH (100:0→95:5) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield a white solid, 44.3 mg (69% yield). 1H NMR (DMSO-d6, 400 MHz): δ=1.13-1.22 (m, 9 H), 1.46-1.59 (m, 4 H), 1.70-1.84 (m, 2 H), 1.91-2.01 (m, 2 H), 2.56-2.68 (m, 1 H), 3.08 (s, 3 H), 3.16-3.24 (m, 2 H), 3.45 (q, J=6.91 Hz, 2 H), 3.61 (br. s., 1 H), 3.91-4.01 (m, 4 H), 4.53 (s, 2 H), 7.25 (dd, J=8.59, 2.27 Hz, 2 H), 7.30 (d, J=7.58 Hz, 1 H), 7.60 (d, J=4.55 Hz, 2 H), 8.46 (s, 1 H), 8.51-8.88 (m, 1 H), 9.87 (br. s., 1 H), 10.58 (br. s., 1 H). MS (ES+): m/z 676.30 [MH+] (TOF, polar).

Provenance & Evidence