Diisopropylethylamine → HCID 135431014, compound

Participants

Reaction Steps

7-Amino-4-hydroxy-3-(4-methoxy-phenylazo)-napthalene-2-sulfonic acid isopropyl ester (Example 6, 200 mg, 0.48 mmol ) was dissolved in dichloromethane (3 mL) and diisopropylethylamine (160 μL, 114 mg, 0.96 mmol ) was added. 3,5-Dimethoxybenzoyl chloride (111 mg, 0.6 mmol ) was added under nitrogen. The reaction mixture was allowed to stir for 16 h. The suspension was filtered to provide the title compound (110 mg, 0.19 mmol, 40% ) as a red solid: NMR (DMSO-d6): δ 10.72 (s, 1H). 8.46 (s, 1H), 8.32 (d, 9 Hz, 1H), 8.05 ( d, 9 Hz, 1H), 7.80 (d, 9 Hz, 3H), 7.12 (m, 4H), 6.79 (s, 1H), 4.86 (m, 1H), 3.86 (m, 9H), 1.22 (d, 6 Hz, 6H). Analytical HPLC: 87% pure. MS (ES-NEG): [M−H] 578; Anal. Calc. for C29H29N3O8S: C, 60.09, H, 5.04, N, 7.25. Found: C, 57.60, H, 5.17, N, 6.88.

Provenance & Evidence