Reaction Steps
A solution of the isothiocyanate 25 (18.9 mg, 0.02986 mmol), triethylamine (7.26 mg, 0.07175 mmol), anisidine (6.9 mg, 0.05602 mmol), and CHCl3 (15 mL) was refluxed for 3 hours and the solvent was removed in vacuo. Flash chromatography of this crude product using 100% EtOAc gave the anisidine derivative 26 as a clear oil (19.8 mg, 87.6% yield). 1H NMR (in CDCl3): δ8.17 (brs,lH,NH--CS--NH--Ar), 7.28 (d,j=8.8 Hz,2H,H2 &H6 --Ar--N), 7.15 (d,j=8.6 Hz,4H,2H3 &H5 --Ar--OCH3), 7.06 (brs,lH,NH--CS--NH--Ar), 7.06 (t,j=5.7 Hz,2H,2NH--CO), 6.90 (d,j=8.9 Hz,2H,H3 &H5 --Ar--N), 6.82 (d,j=8.6 Hz,4H,2H2 &H6 --Ar--OCH3), 3.79 (s,3H,CH3O--Ar--N), 3.77 (s,6H,2CH3O--Ar--CH2), 3.67 (s,4H,2S--CH2 -Ar), 3.61 (q,j=5.3 Hz,2H,N--CH2CH2 --NHCS), 3.14 (q,j=6.2 Hz,4H,2N-CH 2CH2 --NHCO), 2.69 (t,j=5.6 Hz,2H,N--CH2CH2 --NHCS), 2.52 (t,j=6.3Hz,4H 2N--CH2CH2 --NH--CO), 1.51 (br s,12H,4CH3 --C--S) ppm. 13C NMR (in CDCl3): δ181.9 (s,N--CS--N), 175.2 (s,2NH--CO), 158.8 (s,3C1 --Ar--OCH3), 130.0 (s,C1 --Ar--N), 130.0 (d,2C2 &C6 --Ar--OCH3), 129.2 (s,2C4 --Ar--OCH3), 127.0 (d,C2 &C6 --Ar--N), 114.5 (d,C3 &C5 --Ar--N), 114.2 (d,2C3 &C5 --Ar--OCH3), 55.4 (q,3CH3O), 54.4 (t,2N-CH 2CH2 --NHCO), 52.9 (t,N--CH2CH2 --NHCS), 50.1 (s,2S--C--CH3), 42.8 (t,N--CH2CH2 --NHCS), 38.3 (t,2N--CH2CH2 --NHCO), 34.2 (t,2S--CH2 --Ar), 28.3 (q,4CH3 --C--S) ppm. MS (m/z,FAB): 756(4.2, M+). IR (CDCl3): 3320, 2960, 1720, 1655, 1510, 1290, 1245, 1030 cm-1.
