2,4-Difluorobenzoyl chloride → [4-(2,4-Diaminoquinazolin-5-yloxymethyl)piperidin-1-yl]-(2,4-difluorophenyl)methanone

Participants

Reaction Steps

The amidation of 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (50 mg; 0.18 mmol) was carried out using 2,4-difluorobenzoyl chloride (65 mg; 0.37 mmol) via Method AA to yield 108 mg. (71% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.48 (m, 1H), 7.35 (m, 2H), 7.18 (m, 3H), 6.77 (d, J=8.0 Hz, 1H), 6.54 (d, J=8.0 Hz, 1H), 5.94 (br s, 2H), 4.53 (br d, J=13.2 Hz, 1H), 4.03 (d, J=6.0 Hz, 2H), 3.44 (m, 1H), 3.12 (t, J=12.8 Hz, 1H), 2.85 (m, 1H), 2.22 (m, 1H), 1.9 (d, J=12.4 Hz, 1H), 1.74 (d, J=12.4 Hz, 1H), 1.26 (m, 2H). MS m/z (ESI) 414 (M+H)+.

Provenance & Evidence