Trifluoroacetic acid → HCID 9968570, compound

HRID 1005666Notes

Reaction equation

HRID 1005666 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][C:20]([CH3:23])=[C:19]3[S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:27]1([S:24]([C:19]2[C:18]3[C:22](=[C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:15]=[CH:16][CH:17]=3)[NH:21][C:20]=2[CH3:23])(=[O:25])=[O:26])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60108787HCID 60108787, compound

Product 1

HCID 9968570HCID 9968570, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Benzenesulfonyl-2-methyl-1H-indol-7-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.25 g) was dissolved in 2 mL of dichloromethane and 2 mL of trifluoroacetic acid was added. After 10 min the mixture was concentrated in vacuo, taken into water, and washed with ether. The aqueous layer was basified with ammonium hydroxide, extracted with dichloromethane, and the extract was dried (sodium sulfate) and evaporated to afford the crude free base which was crystallized from dichloromethane-ether to afford 35 mg of 3-benzenesulfonyl-2-methyl-7-piperazin-1-yl-1H-indole (601), m.p. 188-190° C.

Workup

  1. concentrationAfter 10 min the mixture was concentrated in vacuo
  2. washwashed with ether
  3. extractionextracted with dichloromethane
  4. dry with materialthe extract was dried (sodium sulfate)
  5. customevaporated
  6. customto afford the crude free base which
  7. customwas crystallized from dichloromethane-ether

Sources & evidence

ORD record
ord-6f61945af7734f148ea64f9abc413594
Source dataset
uspto-grants-2004_09
Patent number
US06787535B2

Reaction notes

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