3-Aminophenylboronic acid → 6-[3-[(4,5-dihydro-1H-imidazol-2-yl)amino]phenyl]-(alphaS)-3,4-dihydro-4-oxo-alpha-[[(phenylmethoxy)carbonyl]amino]-2-quinazolinepropanoic Acid

Participants

Reaction Steps

Compound 9 was prepared as described for Compound 1, but instead of Compound AA2, N-carbobenzyloxyasparagine tert-butyl ester (8.2 g) was reacted with Compound AA3 and produced Compound AC1. Scheme AC shows the Suzuki cross coupling of Compound AC1 with 3-aminophenylboronic acid to produce Compound AC2. As shown in the illustration for Scheme AA, intermediate Compound AC2 (0.19 g) was converted to the corresponding 2-aminoimidazoline by coupling with Compound AA5 followed by hydrolysis to yield Compound 9. Compound 9 was isolated as a white solid (TFA salt): 1H NMR (DMSO, d6) δ 3.0 (m, 1 H), 3.2 (m, 1 H), 3.4 (m, 2 H), 3.6 (s, 4H), 4.7 (m, 1 H), 5.0 (s, 2 H), 7.0 (m, 1 H), 7.3 (m, 5 H), 7.5 (m, 2 H), 7.7 (d, J=8 Hz, 1 H), 7.8 (d, J=8 Hz, 1 H), 8.1 (d, J=8 Hz, 1 H), 8.3 (s, 1 H); MS m/e 527 (MH+).

Provenance & Evidence