3-Methylbenzoyl chloride → [4-(2,4-Diaminoquinazolin-5-yloxymethyl)piperidin-1-yl]-m-tolylmethanone

Participants

Reaction Steps

The amidation of 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (50 mg; 0.18 mmol) was carried out using m-toluoyl chloride (56 mg; 0.36 mmol) via Method AA to yield 47 mg. (66% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.34 (m, 2H), 7.26 (m, 2H), 7.12 (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 s, 1H), 4.03 (d, J=6.0 Hz, 2H), 3.63 (br s, 1H), 3.08 (br s, 1H), 2.82 (br s, 1H), 2.34 (s, 3H), 2.21 (m, 1H), 1.86 (br s, 1H), 1.75 (br s, 1H), 1.31 (m, 2H). MS m/z (ESI) 392 (M+H)+.

Provenance & Evidence