O-Phenylenediamine → HCID 85417831, compound

Participants

Reaction Steps

A solution of 100 mg (0.31 mmol) 5-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyleneaminooxymethyl)-thiophene-2-carboxylic acid, 65 mg (0.47 mmol) 1-hydroxybenzotriazol, 92 mg (0.47 mmol) N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide and 65 μl (0.47 mmol) triethylamine in 3 ml dichloromethane was stirred for 15 minutes. After addition of 68 mg (0.63 mmol) phenylenediamine the reaction mixture was stirred overnight. The solvent was evaporated and the residue was subjected to preparative HPLC to yield 88 mg (0.21 mmol) 5-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyleneaminooxymethyl)-thiophene-2-carboxylic acid (2-amino-phenyl)-amide (17); exact MW [M+H] calc'd: 410.12; MW found [M+H]: 410.2. 1H-NMR (400 MHz, (CH3)2SO): δ=9.67 (s, 1H), 8.18 (s, 1H), 7.85 (m, 1H), 7.20 (m, 1H), 7.14–7.09 (m, 3H), 6.97 (m, 1H), 6.91 (m, 1H), 6.77 (m, 1H), 6.58 (m, 1H), 5.29 (s, 2H), 4.90 (s, 2H), 4.26 (m, 4H)

Provenance & Evidence