Trifluoroacetic acid → 7-Iodo-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one

HRID 1037292Notes

Reaction equation

HRID 1037292 reaction equation
CN(C)S([N:6]1[C:10]2=[C:11]3[C:16](=[CH:17][CH:18]=[C:9]2[CH:8]=[N:7]1)[C:15](=[O:19])[C:14]([I:20])=[C:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[O:12]3)(=O)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[I:20][C:14]1[C:15](=[O:19])[C:16]2[C:11]([O:12][C:13]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[C:10]1[NH:6][N:7]=[CH:8][C:9]1=[CH:18][CH:17]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670678327-Iodo-6-oxo-8-phenyl-6H-9-oxa-1,2-diaza-cyclopenta[a]naphthalene-1-sulfonic acid dimethylamide

Product 1

HCID 670677727-Iodo-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-iodo-6-oxo-8-phenyl-6H-9-oxa-1,2-diaza-cyclopenta[a]naphthalene-1-sulfonic acid dimethylamide (82 mg, 0.166 mmol) in DCM (2 mL) was added TFA (0.5 mL) at RT. After 3 h, the reaction mixture was concentrated in vacuo to afford the title compound as a white solid (64 mg, 100%). LCMS (Method A): RT=4.23 min, [M+H]+=389.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f3a95162d6f046c38122ffcd9d8733df
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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