Acetyl chloride → HCID 58710695, compound

Participants

Reaction Steps

N,N-Diisopropylethylamine (52 μl) and acetyl chloride (21 μl) were added sequentially, each in one portion, to a stirred mixture of N-(3-chloro-4-fluorophenyl)-7-methoxy-5-[(2R)-pyrrolidin-2-ylmethoxy]-quinazolin-4-amine (100 mg) in DCM (2 ml) at room temperature. The reaction mixture was stirred for 1 hour and then diluted with DCM (10 ml) and washed with saturated aqueous sodium hydrogen carbonate. The organic layer was dried (MgSO4) and concentrated in vacuo to leave a yellow solid, which was purified by column chromatography using 24% methanol in DCM as eluent, followed by trituration with ether to give the title compound as a white solid (92 mg, 83%); NMR Spectrum (DMSO-d6) 9.90 (br s, 1H), 8.40 (s, 1H), 8.15 (m, 1H), 7.65 (m, 1H), 7.40 (m, 1H), 6.80 (m, 2H), 4.60 (m, 1H), 4.50 (m, 1H), 4.25 (m, 1H), 3.95 (s, 3H), 3.50 (m, 1H), 3.30 (s, 3H), 2.0-1.85 (m, 5H); Mass spectrum MH+ 445.

Provenance & Evidence