2-Amino-5-methylthiazole → 2,2-Dimethyl-trans-N-(5-methylthiazol-2-yl)-3-phenylcyclopropanecarboxamide
Reaction equation
[CH3:1][C:2]1([CH3:14])[C@@H:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@@H:3]1[C:11]([OH:13])=O.[NH2:15][C:16]1[S:17][C:18]([CH3:21])=[CH:19][N:20]=1>>[CH3:14][C:2]1([CH3:1])[C@@H:4]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@@H:3]1[C:11]([NH:15][C:16]1[S:17][C:18]([CH3:21])=[CH:19][N:20]=1)=[O:13]Participants
3
Procedure
2,2-Dimethyl-trans-3-phenylcyclopropanecarboxylic acid (250 mg, 1.32 mmol) and 2-amino-5-methylthiazole (150 mg, 1.31 mmol) were reacted as described under General Procedure D to furnish the title compound (232 mg, 61%) as a yellow foam. 1H NMR (300 MHz, CDCl3) δ 7.33-7.17 (m, 6H), 7.02 (s, 1H), 2.95 (d, J=5.6 Hz, 1H), 2.37 (s, 3H), 2.08 (d, J=5.6 Hz, 1H), 1.44 (s, 3H), 1.03 (s, 3H). mp 132-135° C. ESIMS m/z [M+H]+ 287.1.