Dimethylformamide → HCID 67497612, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(pyridin-4-yl)thiazol-5-amine (0.987 g, 5.57 mmol), (S)-2-(tert-butoxycarbonyl)-3-(4-fluorophenyl)propanoic acid (1.58 g, 5.57 mmol), HBTU (2.11 g, 5.57 mmol) and N-ethyl-N-isopropylpropan-2-amine (2.43 ml, 13.9 mmol) in N,N-dimethylformamide (11.1 ml, 5.57 mmol) was allowed to stir at 80° C. for 4 hours. 20 mL of water was added and the resulting mixture was extracted with DCM (40 mL×4). The extract was dried and concentrated. The residue was purified by CombiFlash using 0-10% methanol/DCM to give 250 mg of (S)-tert-butyl 3-(4-fluorophenyl)-1-oxo-1-(2-(pyridin-4-yl)thiazol-5-ylamino)propan-2-ylcarbamate 5.2A. 400 MHz 1H NMR (CD3OD) δ: 8.78 (d, 2H), 8.43 (d, J=8.0 Hz, 2H), 7.87 (s, 1H), 7.27 (dd, J=8.0, 4.0 Hz, 2H), 7.01 (dd, 2H), 4.50 (m, 1H), 3.15 (m, 1H), 2.99 (m, 1H), 1.40 (s, 9H). LCMS (ES+) m/z 443.

Provenance & Evidence