N-Hydroxysuccinimide → N-(4-methoxy-phenyl)-N-(succinimidyl-oxycarbonyl-propyl-sulfonyl)-furo[2,3-b]quinoline-4-carboxamide

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([S:25]([CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])(=[O:27])=[O:26])[C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]3[O:22][CH:23]=[CH:24][C:13]=23)=[O:11])=[CH:5][CH:4]=1.O1CCN(CC[N+]#[C-])CC1.O[N:45]1[C:49](=[O:50])[CH2:48][CH2:47][C:46]1=[O:51]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([S:25]([CH2:28][CH2:29][CH2:30][C:31]([O:33][N:45]2[C:49](=[O:50])[CH2:48][CH2:47][C:46]2=[O:51])=[O:32])(=[O:26])=[O:27])[C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]3[O:22][CH:23]=[CH:24][C:13]=23)=[O:11])=[CH:7][CH:8]=1

Participants

Reactant 3

HCID 80170N-Hydroxysuccinimide

HCID 27594344-(2-Isocyanoethyl)morpholine

HCID 68637975N-(4-Methoxy-phenyl)-N-(carboxypropyl-sulfonyl)-furo[2,3-b]quinoline-4-carboxamide

Product 1

HCID 86607521N-(4-methoxy-phenyl)-N-(succinimidyl-oxycarbonyl-propyl-sulfonyl)-furo[2,3-b]quinoline-4-carboxamideYield 63.9%

Procedure

A mixture of 140 mg (0.26 mmol) N-(4-Methoxy-phenyl)-N-(carboxypropyl-sulfonyl)-furo[2,3-b]quinoline-4-carboxamide 10, 54 μl (0.37 mmol) 2-Morpholino-ethyl-isocyanide (MEI) and 44 mg (0.37 mmol) N-Hydroxysuccinimide (HOSu) was stirred overnight at room temperature. The solvent was removed under vacuum and the oily residue was purified by silica gel column chromatography (eluent: methylene chloride/acetone 9:1+0.1% acetic acid). The appropriate fractions were combined and evaporated to yield 94 mg of 11.