1-(2-Chloroacetyl)indoline → N-({4-[2-(2,3-Dihydro-1H-indol-1-yl)-2-oxoethyl]morpholin-2-yl}methyl)-N'-phenylurea

Participants

Reaction Steps

To a stirred solution of Intermediate 7 (0.01 g) in N,N-dimethylformamide (0.5 ml) was added 1-(2-chloroacetyl)indoline (0.0092 g). The mixture was stirred at 22° C. for 17 h before tris-(2-aminoethyl)amine polystyrene (Argonaut Technologies, 0.01 g @ 4.46 mmol/g) and polystyrene methyl isocyanate (Argonaut Technologies, 0.033 g @ 1.39 mmol/g) was added. Stirring was continued for a further 30 min before the mixture was purified by solid phase extraction (1 g Isolute SCX sulphonic acid column), eluting with methanol followed by 10% 0.880 ammonia solution in methanol. The basic fraction was evaporated in vacuo to give the title compound as a white solid (0.012 g). LC/MS (System A) Rt 2.69 min, Mass Spectrum m/z 394 [MH+].

Provenance & Evidence