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

HRID 641137Notes

Reaction equation

HRID 641137 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

4

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 27594344-(2-Isocyanoethyl)morpholineHCID 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.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe oily residue was purified by silica gel column chromatography (eluent: methylene chloride/acetone 9:1+0.1% acetic acid)
  3. customevaporated

Sources & evidence

ORD record
ord-fcf418860960474dabba75e364298a68
Source dataset
uspto-grants-2010_04
Patent number
US07695980B2

Reaction notes

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