1-Chloropyrrolo[1,2-a]pyrazine → HCID 75204315, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the crude amine in 0.16 mL of diisopropylethylamine was added 1-chloropyrrolo[1,2-a]pyrazine (0.047 g, 0.31 mmol) followed by 1 drop of 1-butyl-3-methylimidazolium tetrafluorborate. The reaction was heated at 90° C. for 20 h. Purification of the residue by HPLC afforded (S)-6-chloro-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)quinazoline-2-carboxamide (0.05 g, 0.013 mmol, 6%). 1H NMR (400 MHz, CD3OD) δ 9.60 (s, 1 H), 8.26(s, 1 H), 8.17 (d, J=9.1 Hz, 1 H), 8.07 (dd, J=1.8, 9.1 Hz, 1 H), 7.76 (d, J=1.5 Hz, 1 H), 7.72 (d, J=5.8 Hz, 1 H), 7.57 (s, 1 H), 6.93 (m, 1 H), 6.85 (d, J=5.8 Hz, 1 H), 5.06-4.84 (m, 1 H), 4.82-3.60 (br, 4 H), 2.65-2.40 (br, 2 H); MS: (ES) m/z calculated for C20H17ClN6O [M+H]+ 393.2, found 393.

Provenance & Evidence