Trifluoroacetic acid → HCID 68494150, compound

HRID 1038765Notes

Reaction equation

HRID 1038765 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:17]([CH3:45])[C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([O:25][C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:44])[C:34]4[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=4)=[CH:28][N:27]=2)=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[CH3:45][N:17]1[C:18]2[C:23](=[CH:22][C:21]([O:25][C:26]3[N:27]=[CH:28][C:29]([NH:32][C:33](=[O:44])[C:34]4[CH:39]=[CH:38][C:37]([C:40]([F:42])([F:41])[F:43])=[CH:36][CH:35]=4)=[CH:30][CH:31]=3)=[CH:20][CH:19]=2)[CH:24]=[C:16]1[C:14]([N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:15]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68497191HCID 68497191, compound

Product 1

HCID 68494150HCID 68494150, compoundYield 87.9%

Procedure

To 4-{1-methyl-5-[5-(4-trifluoromethylbenzoylamino)-pyridin-2-yloxy]-1H-indole-2-carbonyl}piperazine-1-carboxylic acid tert-butyl ester (2.75 g, 4.41 mmol) was added trifluoroacetic acid (16 mL) under ice cooling. The reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was evaporated under reduced pressure. The residue was made alkaline with 5 M NaOH, and extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford 2.03 g of the title compound as a yellow amorphous powder.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e0fa7b0fc4894d1f8e749420761448f3
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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