2-Amino-4-methylthiazole → HCID 50990952, compound

Participants

Reaction Steps

Compound 2 (3.0 g, 14 mmol, 1.0 eq), 4-methylthiazol-2-amine (1.66 g, 14.5 mmol, 1.05 eq), 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (5.54 g, 14.5 mmol, 1.05 eq), and DIEA (2.6 mL, 15 mmol, 1.1 eq) were dissolved in DMF (69 mL) and stirred overnight at rt. The reaction was diluted with EtOAc and washed with H2O (2×). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by preparative HPLC afforded 1.5 g (35%) of the title compound as an off-white powder: 1H NMR (400 MHz, DMSO-d6) δ 8.65 (d, J=5.5 Hz, 1H), 8.59-8.57 (m, 2H), 7.79 (d, J=8.4 Hz, 1H), 7.60-7.56 (m, 2H), 7.31 (dd, J=5.5, 2.4 Hz, 1H), 6.89 (s, 1H), 2.29 (s, 3H); ES-MS [M+1]+: 313.1.

Provenance & Evidence