Triethylamine → HCID 57415394, compound

Reaction equation

[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][C:8]2[S:12][C:11]([NH2:13])=[N:10][N:9]=2)=[CH:5][CH:4]=1.CCN(CC)CC.[CH3:23][C:24]1[O:28][C:27]([CH2:29][CH2:30][C:31](Cl)=[O:32])=[CH:26][CH:25]=1>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[S:12][C:11]([NH:13][C:31](=[O:32])[CH2:30][CH2:29][C:27]3[O:28][C:24]([CH3:23])=[CH:25][CH:26]=3)=[N:10][N:9]=2)=[CH:14][CH:15]=1

Participants

Procedure

To a solution of 5-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (88b, 221 mg, 1.0 mmol), Et3N (0.38 ml) in 1,4-dioxane (8.0 ml) was slowly added 3-(5-methylfuran-2-yl) propanoyl chloride and stirred for further 16.0 hours at room temperature. The reaction mixture was then quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s), and concentrated under reduced pressure to give N-[5-(4-methoxy-benzyl)-[1,3,4]thiadiazol-2-yl]-3-(5-methyl-furan-2-yl)-propionamide (88): 1H NMR (500 MHz, DMSO) δ7.24(d, 2H), δ6.89(d, 2H), δ5.90(d, 2H), δ4.24(s, 2H), δ3.72(s, 3H), δ2.83 (d, 3H), δ2.71(d, 2H), δ2.17(s, 3H). ESI-MS: 358.0 (M+H)+.