Trifluoroacetic acid → HCID 22124487, compound

HRID 1858072Notes

Reaction equation

HRID 1858072 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:37])=[C:24]([NH:27][C:28](=[O:36])[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)[CH:25]=2)[NH:20][C:19](=[O:38])[C:18]=1[C:39]1[CH:44]=[C:43]([CH3:45])[CH:42]=[C:41]([CH3:46])[CH:40]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[Cl:37][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:39]3[CH:44]=[C:43]([CH3:45])[CH:42]=[C:41]([CH3:46])[CH:40]=3)[C:19](=[O:38])[NH:20]2)=[CH:25][C:24]=1[NH:27][C:28](=[O:36])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54012627HCID 54012627, compound

Product 1

HCID 22124487HCID 22124487, compound

Procedure

To a solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(2-pyridin-2-yl-acetylamino)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (55 mg in 4.0 mL methylene chloride) was added 2.0 mL trifluoroacetic acid and the mixture stirred at room temperature. After 20 minutes, the mixture was concentrated in vacuo, resolvated in 10% ammonium hydroxide in methanol and concentrated once again. Purification by flash chromatography on silica gel (methylene chloride:10% ammonium hydroxide in methanol, 95:5; then 90:10) gave the title compound, 40 mg.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. concentrationconcentrated once again
  3. customPurification by flash chromatography on silica gel (methylene chloride

Sources & evidence

ORD record
ord-e5ae64b1122147e4bd05594af08271f5
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

Loading…