Trifluoroacetic acid → 7-chloro-3-(3,5-dimethylphenyl)-6-(3-oxo-3-pyrrolidin-1-yl-propyl)-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-one

HRID 1858098Notes

Reaction equation

HRID 1858098 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]([CH2:27][CH2:28][C:29](=[O:35])[N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[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>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:39]=[C:40]([CH3:45])[CH:41]=[C:42]([CH3:44])[CH:43]=3)[C:19](=[O:37])[NH:20]2)=[CH:25][C:24]=1[CH2:27][CH2:28][C:29](=[O:35])[N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 536595522-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(3-oxo-3-pyrrolidin-1-yl-propyl)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 221245057-chloro-3-(3,5-dimethylphenyl)-6-(3-oxo-3-pyrrolidin-1-yl-propyl)-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-oneYield 92.3%

Reagents, catalysts & solvents 1

HCID 7519AnisoleCatalyst

Procedure

To a solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(3-oxo-3-pyrrolidin-1-yl-propyl)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (9.0 mg in 2.0 dry 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, 9:1) to give the title compound (7.0 mg). MASS: 536 (M+H)

Workup

  1. customAfter 30 minutes the solvents were removed in vacuo
  2. customthe resulting residue purified by flash chromatography on silica gel (methylene chloride:10% ammonium hydroxide in methanol, 9:1)

Sources & evidence

ORD record
ord-6e53d0022f4640e78222148e7323de31
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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