2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-1-methyl-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester → 7-chloro-3-(3,5-dimethylphenyl)-1-methyl-6-nitro-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-one

HRID 1857648Notes

Reaction equation

HRID 1857648 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:30])=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=2)[N:20]([CH3:31])[C:19](=[O:32])[C:18]=1[C:33]1[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[CH:34]=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][CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]3)=[C:18]([C:33]3[CH:34]=[C:35]([CH3:40])[CH:36]=[C:37]([CH3:39])[CH:38]=3)[C:19](=[O:32])[N:20]2[CH3:31])=[CH:25][C:24]=1[N+:27]([O-:29])=[O:28]

Participants

4

Reactant 1

HCID 537246792-{2-[7-Chloro-3-(3,5-dimethylphenyl)-1-methyl-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 221299777-chloro-3-(3,5-dimethylphenyl)-1-methyl-6-nitro-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-1-methyl-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (ca. 100 mg crude from EXAMPLE17, StepB in a mixture of 1 mL trifluoroacetic acid and 0.01 mL anisole) was stirred at room temperature for 1 hour. The mixture was then concentrated in vacuo, resolvated in methylene chloride and washed with saturated sodium bicarbonate. The concentrated organics were purified by flash chromatography on silica gel (chloroform:1% ammonium hydroxide in methanol:, 9:1) to give the title compound (22 mg). MASS: 470 (M+H)

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. washwashed with saturated sodium bicarbonate
  3. customThe concentrated organics were purified by flash chromatography on silica gel (chloroform:1% ammonium hydroxide in methanol:, 9:1)

Sources & evidence

ORD record
ord-84ef600a801d4a33a923eef451ebeefd
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

Loading…