Diisopropylethylamine → HCID 178476577, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylethylamine (0.16 mL, 0.92 mmol) was added to a solution of {4-[4-(4-{bis-[2-(4-hydroxy-3-formylaminophenyl)-2-(R)-hydroxyethyl]amino}-butyl)phenyl]butyl}amine diacetic acid salt (13) (129 mg, 019 mmol) in absolute ethanol (4 mL). The mixture was stirred at 70° C. (oil bath) for 10 min, after which 1-(3,5-diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (79 mg, 0.20 mmol) was added in one portion. The reaction mixture was stirred at that temperature for 3 h and cooled to rt. The solvent was removed by rotary evaporation. The residue was purified by Biotage silica gel column chromatography (A=dichloromethane, B=10% concentrated aqueous ammonium hydroxide in methanol, gradient B/A 1% to 25%) to give the desired adduct 14 as a greenish yellow solid (44 mg, 26%): 1H NMR (500 MHz, DMSO-d6) δ 1.50 (m, 8H), 1.98 (s, 6H), 2.58 (m, 4H), 3.20 (m, 8H), 4.45 (m, 2H), 6.60 (br, 2H), 6.80 (m, 4H), 7.08 (m, 4H), 8.00 (s, 2H), 8.28 (s, 2H), 9.56 (br, 2H); m/z (ESI) 791 [C38H47ClN10O7+H]+; [α]D25 −4.0° (c 0.35, MeOH); mp 128-130° C.

Provenance & Evidence