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

HRID 641141Notes

Reaction equation

HRID 641141 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[S: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[S: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 68637627N-(4-Methoxy-phenyl)-N-(carboxypropyl-sulfonyl)-thieno[2,3-b]quinoline-4-carboxamide

Product 1

HCID 86607522N-(4-Methoxy-phenyl)-N-(succinimidyl-oxycarbonyl-propyl-sulfonyl)-thieno[2,3-b]quinoline-4-carboxamideYield 107.5%

Procedure

A mixture of 66 mg (0.12 mmol) N-(4-Methoxy-phenyl)-N-(carboxypropyl-sulfonyl)-thieno[2,3-b]quinoline-4-carboxamide 17, 25 μl (0.17 mmol) 2-Morpholino-ethyl-isocyanide (MEI) and 21 mg (0.17 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 75 mg of 18.

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-577e719816694efea57b62b8871923ab
Source dataset
uspto-grants-2010_04
Patent number
US07695980B2

Reaction notes

Loading…