2-Amino-4-methylthiazole → HCID 86762172, compound

Participants

Reaction Steps

Compound 6 (30 mg, 0.14 mmol, 1.0 eq), 4-methylthiazol-2-amine (19 mg, 0.17 mmol, 1.2 eq), O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (110 mg, 0.289 mmol, 2.10 eq), and N,N-Diisopropylethylamine (38 mg, 0.29 mmol, 2.1 eq) were dissolved in CH2Cl2 (1.5 mL) and DMF (0.30 mL) and stirred at rt for 72 h. The reaction was quenched with water, and the layers were separated via phase separation. The organic layer was dried on air concentrator and purified by reverse-phase preparatory HPLC to afford 17 mg (38%) of the title compound as a mono-TFA salt: 1H NMR (400 MHz, DMSO-d6) δ 9.01 (d, J=1.7 Hz, 1H), 8.69 (d, J=2.8 Hz, 1H), 8.56 (d, J=2.8 Hz, 1H), 8.49 (dd, J=4.7, 1.2 Hz, 1H), 8.04 (t, J=2.2 Hz, 1H), 7.68 (ddd, J=8.4, 2.8, 1.2 Hz, 1H), 7.54 (dd, J=8.4, 4.7 Hz, 1H), 7.23 (d, J=1.2 Hz, 1H), 2.36 (d, J=1.0, 3H); ES-MS [M+1]+:313.1.

Provenance & Evidence