1-Hydroxybenzotriazole → HCID 136331244, compound

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Reaction Steps

A solution of 3-formyl-5-methyl-benzoic acid (3.80 g, 23.2 mmol), HOBt (4.17 g, 27.8 mmol) and EDC HCl (4.44 g, 23.2 mmol) in DMF (200 mL) was stirred at rt for 5 min before 3-ethyl-4,N-dihydroxy-5-methyl-benzamidine (4.50 g, 23.2 mmol) was added. The mixture was stirred at rt for 1 h. The mixture was heated to 75° C. and stirring was continued for 3 h. The mixture was concentrated to about 40 mL, acidified by adding formic acid (0.6 mL), diluted with a small amount of acetonitrile/water and separated by prep. HPLC (Waters XBridge Prep C18, 50×50 mm+50×100 mm, 10 μm, 80% to 10% water (containing 0.5% of formic acid) in MeCN) to give the title compound as a white solid (2.14 g). LC-MS**: tR=0.82 min; [M+1]+=323.15, 1H NMR (D6-DMSO): δ 1.20 (t, J=7.3 Hz, 3H), 2.28 (s, 3H), 2.55 (s, 3H), 2.69 (q, J=7.5 Hz, 2H), 7.71 (d, J=2.0 Hz, 2H), 8.05 (s, 1H), 8.32 (s, 1H), 8.49 (s, 1H), 8.95 (s, 1H), 10.14 (s, 1H).

Provenance & Evidence