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

HRID 1857607Notes

Reaction equation

HRID 1857607 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[Cl:30][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([O:16][CH2:15][CH2:14][C@@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]3)=[C:18]([C:32]3[CH:33]=[C:34]([CH3:39])[CH:35]=[C:36]([CH3:38])[CH:37]=3)[C:19](=[O:31])[NH:20]2)=[CH:25][C:24]=1[N+:27]([O-:29])=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15895694HCID 15895694, compound

Product 1

HCID 10004181(S)-7-chloro-3-(3,5-dimethylphenyl)-6-nitro-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 7519AnisoleCatalyst

Procedure

To a solution of (S)-2-{2-[7-chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (35 mg in 2 mL dry methylene chloride) was added 2 drops of anisole followed by 2 mL of trifluoroacetic acid and the mixture stirred at room temperature. After 30 minutes the solvents were removed in vacuo. The residue was azeotroped in vacuo successively from 2 mL carbon tetrachloride, 2 mL chloroform and 2 mL methylene chloride and the final concentrate purified by preparative tlc on silica gel (chloroform: 10% ammonium hydroxide in methanol, 90:10) to give the title compound, 17 mg.

Workup

  1. customAfter 30 minutes the solvents were removed in vacuo
  2. customThe residue was azeotroped in vacuo successively from 2 mL carbon tetrachloride, 2 mL chloroform and 2 mL methylene chloride
  3. concentrationthe final concentrate
  4. custompurified by preparative tlc on silica gel (chloroform: 10% ammonium hydroxide in methanol, 90:10)

Sources & evidence

ORD record
ord-7e112cb6cb5342dcbccb2af0cfb134c0
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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