Trifluoroacetic acid → 4-[5-Chloro-3-(2-chlorophenyl)-2,3-dihydro-3-dimethylamino-2-oxoindol-1-yl]methylbenzoic acid

HRID 965565Notes

Reaction equation

HRID 965565 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:24]=[CH:23][C:15]([C:16]([O:18]C(C)(C)C)=[O:17])=[CH:14][CH:13]=1)[C:6](=[O:25])[C:5]2([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Cl:35])[N:26]([CH3:28])[CH3:27].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:24]=[CH:23][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[C:6](=[O:25])[C:5]2([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Cl:35])[N:26]([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19076573tert-Butyl 4-[5-chloro-3-(2-chlorophenyl)-2,3-dihydro-3-dimethylamino-2-oxoindol-1-yl]methylbenzoate

Product 1

HCID 190764264-[5-Chloro-3-(2-chlorophenyl)-2,3-dihydro-3-dimethylamino-2-oxoindol-1-yl]methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.615 g of the compound obtained in EXAMPLE 93 in 2 ml of DCM is cooled to 0° C. and 2 ml of TFA are added. The mixture is stirred for 30 minutes and evaporated under vacuum and the residue is then taken up with DCM and evaporated under vacuum again to give the expected product, which is used as such in the next step.

Workup

  1. customevaporated under vacuum
  2. customevaporated under vacuum again

Sources & evidence

ORD record
ord-0c776678f7e54d0681f774daae7b3d65
Source dataset
uspto-grants-1998_06
Patent number
US05773612

Reaction notes

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