1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tmp269

Participants

Reaction Steps

A mixture of 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid (52 mg, 0.202 mmole), (4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine (50 mg, 0.184 mmole), and EDCI (38.5 mg, 0.202 mmole) in CH2Cl2 (2 ml) was stirred at room temperature for 8 h. The reaction mixture was then diluted with methylene chloride (10 ml), washed with water (5 ml), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by ISCO (silica gel, elute: 2% methanol in CH2Cl2) to give N-((4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide as a white solid product (59 mg, 62% yield): 1H NMR (CDCl3, 500 MHz): 8.49 (s, 1H), 8.22 (d, J=7.5 Hz, 1H), 7.98 (d, J=8.5 Hz, 1H), 7.88 (d, J=8 Hz, 2H), 7.56-7.53 (m, 2H), 7.52 (s, 1H), 7.369-7.31 (m, 3H), 3.97-3.93 (m, 2H), 3.91 (d, J=5.5 Hz, 2H), 3.77-3.74 (m, 2H), 2.36-2.28 (m, 2H), 2.06-2.04 (m, 2H). MS (ESI) m/z: Calculated for C25H21F3N4O3S: 514.13. found: 515.1 (M−H)+.

Provenance & Evidence