2-Aminothiazole → HCID 86659561, compound

Participants

Reaction Steps

A mixture of diisopropyl 3-[4-(diisopropoxy-phosphoryl)-phenoxy]-5-(1-methyl-1H-imidazol-2-ylsulfanyl)-benzoic acid (68 mg, 0.139 mmol), 2-aminothiazole (28 mg, 0.277 mmol), HATU (66 mg, 0.174 mmol), DMA (0.058 mL, 0.35 mmol) and 0.7 mL of DMF were stirred for 16 h at rt, diluted with CH2Cl2, washed with water, brine, dried and evaporated. The residue was adsorbed to SiO2 and subjected to MPLC on a 12 g column of SiO2 eluting with % MeOH in CH2Cl2 (time): 1% (5 min), 2.5% (10 min), 5% (10 min) which provided 50 mg (63%) of the title compound: 1H NMR (500 MHz, DMSO-d6): δ 1.20 (d, 6H, J=6 Hz). 1.28 (d, 6H, J=6 Hz), 3.66 (s, 3H). 4.56 (m, 2H), 6.95 (t, 1H, J=2 Hz), 7.13 (d, 1H, J=1 Hz), 7.15 (dd, 2H, J=8, 3 Hz), 7.30 (br s, 1H), 7.50 (d, 1H, J=1 Hz), 7.55 (d, 1H, J=3 Hz). 7.60 (br s, 1H), 7.67 (br s, 1H), 7.73 (dd, 2H, J=12, 8 Hz); LCMS (m/z): 573.7 [C26H29N4O5PS2+H]+.

Provenance & Evidence