Trifluoroacetic acid → HCID 50991638, compound

HRID 240848Notes

Reaction equation

HRID 240848 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([N:25]4[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]4)=[CH:22][CH:23]=3)[N:18]([C:38]3[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=3)[CH:17]=2)=[CH:12][CH:11]=1>C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([N:25]4[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]4)=[CH:22][CH:23]=3)[N:18]([C:38]3[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=3)[CH:17]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 50991548HCID 50991548, compound

Product 1

HCID 50991638HCID 50991638, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (46 μL, 0.059 mmol) was added to a mixture solution of tert-butyl 4-(3-(4-methoxyphenyl)-1-(pyridin-4-yl)-1H-indol-6-yl)piperazine-1-carboxylate (29 mg, 0.059 mmol) in methylene chloride (1 mL) at room temperature. After stirring for 3 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 (14 mg, 64%) was obtained as yellow 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

Sources & evidence

ORD record
ord-078dc0f7d654424d8350128f0b197f62
Source dataset
uspto-grants-2014_02
Patent number
US08648089B2

Reaction notes

Loading…