Trifluoroacetic acid → HCID 21101692, compound

Participants

Reaction Steps

4-Chloro-7-methylquinoline [obtained from 3-toluidine following the protocol of Krogstad et. al. (De, D., Byers L. D., Krogstad, D. J. J. Heterocyclic Chem. 1997, 34, 315; 1H NMR ([D]6-DMSO), δ 2.55 (s, 3H), 7.60 (m, 1H), 7.75 (d, 1H), 7.90 (s, 1H), 8.10 (d, 1H), 8.80 (d, 1H)) (0.80 g, 4.5 mmol) and 1-tert-butoxycarbonylpiperazine (3.35 g, 18 mmol) are reacted according to method A yielding 475 mg of 4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-7-methylquinoline. After cleaving the Boc group with trifluoroacetic acid (1.8 mL) in CH2Cl2 (1.8 mL), the piperazine is treated with 4-fluorophenyl isocyanate and triethylamine (0.245 mL) according to method C yielding the title product.

Provenance & Evidence