2-Bromo-imidazo[2,1-b]thiazol-6-ylamine hydrochloride → (S,S)-{1-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester
Reaction equation
Cl.BrC1SC2=NC(N)=CN2C=1.[C:12]([O:16][C:17](=[O:45])[NH:18][C@@H:19]([C:39]1[CH:44]=CC=C[CH:40]=1)[C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@@H:23]1[C:27](=[O:38])[NH:28][C:29]1[N:30]=[C:31]2[N:35]([CH:36]=1)[CH:34]=[C:33]([Br:37])[S:32]2)=[O:21])(C)(C)C>>[CH3:12][O:16][C:17](=[O:45])[NH:18][C@H:19]([C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[C:27](=[O:38])[NH:28][C:29]1[N:30]=[C:31]2[N:35]([CH:36]=1)[CH:34]=[C:33]([Br:37])[S:32]2)=[O:21])[CH:39]([CH3:44])[CH3:40]Participants
3
Reactant 2
Product 1
Procedure
Compound 12b was synthesized from compound 11 (0.33 mmol) and compound 3b (0.495 mmol), following the procedure as described for compound 12a, to give compound 12b as a yellow oil in 44% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 0.93 (dd, 6H), 1.70-2.00 (m, 4H), 2.01-2.10 (m, 1H), 3.51 (s, 3H), 3.59 (m, 1H), 3.82 (m, 1H), 4.00 (t, 1H), 4.51 (dd, 1H), 7.34 (d, 1H), 7.80 (s, 1H), 8.15 (s, 1H), 10.64 (s, 1H); MS (ESI, EI+) m/z=472-474 (MH+).