Trifluoroacetic acid → HCID 50991728, compound

HRID 240852Notes

Reaction equation

HRID 240852 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([CH3:47])[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:27]3[C:22](=[CH:23][C:24]([N:28]4[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]4)=[CH:25][CH:26]=3)[N:21]([C:41]3[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=3)[CH:20]=2)=[CH:15][CH:14]=1>C(Cl)Cl>[CH3:8][N:9]([CH3:47])[CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[C:27]3[C:22](=[CH:23][C:24]([N:28]4[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]4)=[CH:25][CH:26]=3)[N:21]([C:41]3[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=3)[CH:20]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 50991642HCID 50991642, compound

Product 1

HCID 50991728HCID 50991728, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.2 mL) was added to a mixture solution of tert-butyl 4-(3-(4-(2-(dimethylamino)ethoxy)phenyl)-1-(pyridin-4-yl)-1H-indol-6-yl)piperazine-1-carboxylate (4.1 mg, 7.6 μmol) in methylene chloride (0.2 mL) at room temperature. After stirring for 15 hours, the reaction solution was concentrated under reduced pressure. After adding ethyl acetate and saturated sodium bicarbonate aqueous solution, the mixture was extracted with ethyl acetate. The collected organic layer was washed with brine and concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The target compound was obtained as white solid.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. additionAfter adding ethyl acetate and saturated sodium bicarbonate aqueous solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe collected organic layer was washed with brine
  5. concentrationconcentrated under reduced pressure
  6. dry with materialby drying with anhydrous magnesium sulfate
  7. customThe target compound was obtained as white solid

Sources & evidence

ORD record
ord-09b5b9bb12324e97b20a4ed64b2365c7
Source dataset
uspto-grants-2014_02
Patent number
US08648089B2

Reaction notes

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