Reaction #712862

Reaction equation

N,N-Diisopropylethylamine

compound 4

2-(4-(2-(2-(2-aminoethoxyl)ethoxy)ethoxy)-3,5-dichlorophenylamino)benzoic acid

fluorescein isothiocyanate

→

desired compound 5

Yield 61.1%

2-(3,5-dichloro-4-(2-(2-(2-(3-(3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-yl)thioureido)ethoxy)ethoxy)ethoxy)phenylamino)benzoic acid

Yield 61.1%

Solvents

DMF

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure

Procedure

N,N-Diisopropylethylamine (10 μL, 0.057 mmol) was added to a solution of the compound 4 (1.9 mg, 0.0035 mmol) and fluorescein isothiocyanate (FITC) (1.2 mg, 0.003 mmol) in DMF (1.0 ml) and the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was subjected to flash column chromatography (silica gel, 1-20% methanol/methylene chloride) to give the desired compound 5 (1.5 mg, 52% yield); 1H NMR (CD3OD, 400 MHz) δ 8.14-8.10 (m, 1H), 7.88 (dd, 1H, J=2.0 Hz, 8.0 Hz), 7.80-7.62 (m, 2H), 7.34-7.30 (m, 1H), 7.24-7.18 (m, 1H), 7.18-7.12 (m, 3H), 6.86-6.78 (m, 1H), 6.72-6.64 (m, 3H), 6.54-6.50 (m, 2H), 4.21-4.04 (m, 4H), 3.92-3.66 (m, 8H); HRMS (ESI+) m/z: calcd for C40H33Cl2N3O10S+H+ 818.1342. found 818.1328 (M+H+).

Source