Diethanolamine → HCID 135462962, compound

Participants

Reaction Steps

7-(4,6-Dichloro-[1,3,5]-triazin-2-ylamino)-4-hydroxy-3-(4-methoxy-phenylazo)-napthalene-2-sulfonic acid isopropyl ester (Example 7, 200 mg, 0.36 mmol) in acetone (3 mL) was stirred under nitrogen with sodium carbonate (38 mg, 0.36 mmol). Diethanolamine (35 μL, 40 mg, 0.36 mmol) was added to the stirred suspension, and the reaction mixture was allowed to stir 60 h. The reaction mixture was diluted with hydrochloric acid (3 mL, 1 N) and filtered. The solid was triturated in methanol/ether (1:3) for 1 h and filtered to provide the title compound (179 mg, 0.28 mmol, 79%) as a red solid: NMR (DMSO-d6): δ 16.28 (s, 1H), 10.61 (s, 1H), 8.45 (s, 1H ), 8.30 (d, J=9 Hz, 1H), 7.88 (m, 2H), 7.76 (d, J=9 Hz, 2H), 7.15 (d, J=9 Hz, 2H), 4.78 (m, 1H), 3.90 (m, 13H), 1.23 (d, J=6 Hz, 6H); Analytical HPLC: 87%.

Provenance & Evidence