Dichloromethane → N-(4-Methoxy-phenyl)-N-(carboxypropyl-sulfonyl)-thieno[2,3-b]quinoline-4-carboxamide

HRID 641140Notes

Reaction equation

HRID 641140 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]([O:33]C(C)(C)C)=[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.C(Cl)Cl>FC(F)(F)C(O)=O>[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]([OH:33])=[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 2

HCID 6344DichloromethaneHCID 68638513N-(4-methoxy-phenyl)-N-(tert-butyl-oxycarbonylpropyl-sulfonyl)-thieno[2,3-b]quinoline-4-carboxamide

Product 1

HCID 68637627N-(4-Methoxy-phenyl)-N-(carboxypropyl-sulfonyl)-thieno[2,3-b]quinoline-4-carboxamideYield 104.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

80 mg (0.13 mmol) N-(4-Methoxy-phenyl)-N-(tert-butyl-oxycarbonylpropyl-sulfonyl)-thieno-[2,3-b]quinoline-4-carboxamide 16 were dissolved in 1.2 mL trifluoroacetic acid and stirred for 30 minutes at room temperature. 50 mg of silica gel and 10 mL of methylene chloride were added and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel (eluent: methylene chloride/diethylether 6:4+0.1% trifluoroacetic acid). Evaporation of the appropriate fractions gave 66 mg of the desired product 17.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was purified by chromatography on silica gel (eluent: methylene chloride/diethylether 6:4+0.1% trifluoroacetic acid)
  3. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-28d3146ff9424d2680cb90e79251ac22
Source dataset
uspto-grants-2010_04
Patent number
US07695980B2

Reaction notes

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