1,1'-Carbonyldiimidazole → HCID 60198467, compound

Participants

Reaction Steps

A 40 mL vial was charged with CDI (0.584 g, 3.60 mmol), 1-(3,4-dichlorophenyl)-3,3,3-trifluoropropan-1-amine (0.929 g, 3.60 mmol), DIPEA (1.88 mL, 10.8 mmol), DCM (7 mL) and DMF (2 mL). The mixture was stirred for 30 min then a solution of 138 (0.750 g, 3.60 mmol) and DIPEA (1.88 mL, 10.8 mmol) in DCM (3 mL) was added and the mixture stirred for 18 h. The reaction mixture was washed with brine (4 mL) and the organic phase isolated and concentrated. The residue was resuspended in EtOAc and washed with brine (2×50 mL) and concentrated in vacuo. The crude product was purified by reverse phase chromatography (Horizen C18 Biotage 40M) eluting with a MeCN/H2O gradient (eluted at ca. 50% MeCN) to afford 925 mg which was separated by chiral HPLC chromatography and repurified as described in example 19 to afford 0.212 g (23%) of I-34 as a white solid: 1H NMR (400 MHz, CD3OD) δ 8.06 (s, 1H), 7.55 (m, 1H), 7.49 (d, 1H), 7.31 (m, 1H), 5.20 (m, 1H), 4.41 (q, 2H), 4.06 (m, 1H), 3.65 (t, 2H), 3.56 (m, 2H), 2.79 (m, 4H), 1.20 (d, 3H); m/z (APCI-pos) M+1=492.0.

Provenance & Evidence