Trifluoroacetic acid → HCID 54549565, compound

HRID 1858094Notes

Reaction equation

HRID 1858094 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:36])=[C:24]([NH:27][S:28]([C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)(=[O:30])=[O:29])[CH:25]=2)[NH:20][C:19](=[O:37])[C:18]=1[C:38]1[CH:43]=[C:42]([CH3:44])[CH:41]=[C:40]([CH3:45])[CH:39]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.C1(OC)C=CC=CC=1>[Cl:36][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([O:16][CH2:15][CH2:14][CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]3)=[C:18]([C:38]3[CH:43]=[C:42]([CH3:44])[CH:41]=[C:40]([CH3:45])[CH:39]=3)[C:19](=[O:37])[NH:20]2)=[CH:25][C:24]=1[NH:27][S:28]([C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)(=[O:30])=[O:29]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53683563HCID 53683563, compound

Product 1

HCID 54549565HCID 54549565, compound

Reagents, catalysts & solvents 2

HCID 7519AnisoleCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(thiophene-2-sulfonylamino)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester in 5 mL methylene chloride was added a few drops of anisole followed by 1.0 mL of trifluoroacetic acid and the mixture stirred at room temperature. After 30 minutes the solvents were removed in vacuo and the resulting residue purified by flash chromatography on silica gel (methylene chloride:10% ammonium hydroxide in methanol, 95:5; then 90:10) to give the title compound.

Workup

  1. customAfter 30 minutes the solvents were removed in vacuo
  2. customthe resulting residue purified by flash chromatography on silica gel (methylene chloride

Sources & evidence

ORD record
ord-5987622a8d6542f0afcc52c76695d777
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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